12705PathwayFarnesene BiosynthesisFarnesene biosynthesis is a pathway that begins in the chloroplast and ends in the cytosol by which isopentenyl diphosphate becomes a farnesene, a set of six closely related chemical compounds which all are sesquiterpenes. alpha-Farnesene and beta-farnesene are isomers, differing by the location of one double bond. Two of the alpha-farnesene stereoisomers are reported to occur in nature. beta-Farnesene has only one naturally occurring isomer . First, isopentenyl diphosphate isomerase catalyzes the reversible synthesis of dimethylallyl diphosphate from isopentenyl diphosphate. This enzyme requires FAD, NAD(P)H, and a divalent cation (e.g. magnesium) as cofactors. Second, geranylpyrophosphate uses magnesium ion as a cofactor to convert dimethylallyl diphosphate into geranyl diphosphate. Third, (2E,6E)-farnesyl diphosphate synthase catalyzes the conversion of geranyl diphosphate into farnesyl diphosphate. Farnesyl diphosphate then must be transported out of the chloroplast and into the cytosol via a predicted farnesyl diphosphate transporter. Three different enzymes then convert farnesyl diphosphate into different farnesenes. (E,E)-alpha-farnesene synthase converts farnesyl diphosphate into (E,E)-alpha-farnesene. Sesquiterpene synthase converts farnesyl diphosphate into (E)-beta-farnesene. Both of these enzymes requires a magnesium or manganese ion as cofactors. A predicted enzyme, (Z,E)-alpha-farnesene synthase is theorized to catalyze the conversion of farnesyl diphosphate into (Z,E)-alpha-farnesene.MetabolicPW012910CenterPathwayVisualizationContext1319517262402#000099PathwayVisualization1266612705Farnesene BiosynthesisFarnesene biosynthesis is a pathway that begins in the chloroplast and ends in the cytosol by which isopentenyl diphosphate becomes a farnesene, a set of six closely related chemical compounds which all are sesquiterpenes. alpha-Farnesene and beta-farnesene are isomers, differing by the location of one double bond. Two of the alpha-farnesene stereoisomers are reported to occur in nature. beta-Farnesene has only one naturally occurring isomer . First, isopentenyl diphosphate isomerase catalyzes the reversible synthesis of dimethylallyl diphosphate from isopentenyl diphosphate. This enzyme requires FAD, NAD(P)H, and a divalent cation (e.g. magnesium) as cofactors. Second, geranylpyrophosphate uses magnesium ion as a cofactor to convert dimethylallyl diphosphate into geranyl diphosphate. Third, (2E,6E)-farnesyl diphosphate synthase catalyzes the conversion of geranyl diphosphate into farnesyl diphosphate. Farnesyl diphosphate then must be transported out of the chloroplast and into the cytosol via a predicted farnesyl diphosphate transporter. Three different enzymes then convert farnesyl diphosphate into different farnesenes. (E,E)-alpha-farnesene synthase converts farnesyl diphosphate into (E,E)-alpha-farnesene. Sesquiterpene synthase converts farnesyl diphosphate into (E)-beta-farnesene. Both of these enzymes requires a magnesium or manganese ion as cofactors. A predicted enzyme, (Z,E)-alpha-farnesene synthase is theorized to catalyze the conversion of farnesyl diphosphate into (Z,E)-alpha-farnesene.Metabolic44456Mevalonate PathwaySubPathway36951039Compound22556798631820Cunillera N, Arro M, Delourme D, Karst F, Boronat A, Ferrer A: Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate synthase genes. J Biol Chem. 1996 Mar 29;271(13):7774-80.12705Pathway568020463089Huang M, Abel C, Sohrabi R, Petri J, Haupt I, Cosimano J, Gershenzon J, Tholl D: Variation of herbivore-induced volatile terpenes among Arabidopsis ecotypes depends on allelic differences and subcellular targeting of two terpene synthases, TPS02 and TPS03. Plant Physiol. 2010 Jul;153(3):1293-310. doi: 10.1104/pp.110.154864. Epub 2010 May 12.12705Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404Cardiomyocyte CL:00007461Homo sapiens9606EukaryoteHuman18Saccharomyces cerevisiae4932EukaryoteYeast4Arabidopsis thaliana3702EukaryoteThale cress12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm49Bathymodiolus platifrons220390EukaryoteDeep sea mussel60Nitzschia sp.0001EukaryoteNitzschia42Bacteria2ProkaryoteBacteria10Drosophila melanogaster7227EukaryoteFruit fly19Schizosaccharomyces pombe4896Eukaryote23Pseudomonas aeruginosa287Prokaryote51Picea sitchensis3332EukaryoteSitka spruce4PeroxisomeGO:00057771CytosolGO:00058295CytoplasmGO:000573713Endoplasmic ReticulumGO:000578335ChloroplastGO:00095073Mitochondrial MatrixGO:000575914Mitochondrial Outer MembraneGO:00057412MitochondrionGO:00057397Endoplasmic Reticulum MembraneGO:000578925Golgi apparatusGO:000579410Cell MembraneGO:000588627Peroxisome MembraneGO:000577815NucleusGO:000563426Golgi apparatus membraneGO:000013911Extracellular SpaceGO:000561512Mitochondrial Inner MembraneGO:00057436LysosomeGO:000576416Lysosomal LumenGO:004320231Periplasmic SpaceGO:00056202Endothelium BTO:00003931LiverBTO:00007597297Nervous SystemBTO:00014845cardiocyteBTO:00015398Blood VesselBTO:000110274115411PW_BS0000052111PW_BS0000028511PW_BS0000081985181PW_BS0000241601181PW_BS00016021013181PW_BS0000242253541PW_BS0000242491341PW_BS0000241115121PW_BS000111122551PW_BS0001221355171PW_BS0001352164181PW_BS000024151141PW_BS0001513344121PW_BS000028408451PW_BS0001153744171PW_BS0000534311PW_BS00000416212PW_BS000016261115PW_BS000026181311PW_BS000018221411PW_BS000022397113PW_BS0000393211PW_BS000003215114PW_BS00002146114PW_BS00004649711PW_BS000049432511PW_BS00004314101PW_BS000014101711PW_BS000010592711PW_BS000059231511PW_BS00002329111PW_BS000029711PW_BS000007311511PW_BS000031918511PW_BS000091541315PW_BS000054562611PW_BS0000561041431PW_BS0001041122121PW_BS000112103331PW_BS0001031471241PW_BS0001471553241PW_BS0001551613181PW_BS00016116611PW_BS0001661783211PW_BS0001781644PW_BS00016419914181PW_BS000024205561PW_BS000024206261PW_BS0000242137181PW_BS0000242111018PW_BS00002421425181PW_BS000024222341PW_BS0000241321121PW_BS0001322881441PW_BS000024226441PW_BS0000242905491PW_BS0000242851041PW_BS0000243081011PW_BS0000241333121PW_BS00013332914121PW_BS0000283361121PW_BS00002833527121PW_BS0000281151012PW_BS0001153317121PW_BS00002835625121PW_BS00002813013121PW_BS0001303683601PW_BS000028184121PW_BS000024372102PW_BS0000281181171PW_BS00011815111PW_BS000015253541PW_BS0000245181PW_BS000051383751PW_BS00010027151PW_BS0000272231241PW_BS000024390761PW_BS0001123987171PW_BS000113406351PW_BS0001153821451PW_BS000100407251PW_BS000115124151PW_BS000124429151PW_BS0001154192551PW_BS0001151251351PW_BS000125405105PW_BS0001154222751PW_BS0001151203171PW_BS00012039914171PW_BS0001131192171PW_BS0001194641171PW_BS00011545525171PW_BS00011513613171PW_BS0001363761017PW_BS00005337527171PW_BS0000532975101PW_BS00002448414101PW_BS0001154793101PW_BS0001154812101PW_BS0001154824101PW_BS0001152991101PW_BS0000244957101PW_BS00011549025101PW_BS0001154781010PW_BS00011549127101PW_BS00011530013101PW_BS0000243891461PW_BS000112501361PW_BS000115502461PW_BS000115388161PW_BS0001125072561PW_BS000115209106PW_BS0000245082761PW_BS0001153951361PW_BS000113101531PW_BS000101171211PW_BS0000179611PW_BS0000092811611PW_BS0000286131PW_BS000006951721PW_BS0000951231751PW_BS000123100521PW_BS00010010813PW_BS00010814117191PW_BS00014111PW_BS000001117131PW_BS000117188118PW_BS0000241632181PW_BS000163224241PW_BS00002429817101PW_BS0000243221231PW_BS000024315123PW_BS00002413412121PW_BS00013433217121PW_BS0000281136121PW_BS00011334713125PW_BS000028943PW_BS0000944251355PW_BS000115126651PW_BS0001263841251PW_BS00010044717171PW_BS00011546013175PW_BS0001154436171PW_BS00011512112171PW_BS00012148012101PW_BS0001153911261PW_BS00011230635511PW_BS0000243211515PW_BS000032892PW_BS000089107313PW_BS0001073183123PW_BS00002412815121PW_BS00012817018PW_BS0001704101551PW_BS00011544415171PW_BS00011548515101PW_BS00011522014PW_BS00002429341PW_BS0000241039Isopentenyl pyrophosphateHMDB0001347Isopentenyl pyrophosphate, IPP or isopentenyl diphosphate, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from Mevalonate-5-pyrophosphate, in a reaction catalyzed by the enzyme mevalonate-5-pyrophosphate decarboxylase. (wikipedia).358-71-4C001291195165841158DB04714CC(=C)CCOP(O)(=O)OP(O)(O)=OC5H12O7P2InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)NUHSROFQTUXZQQ-UHFFFAOYSA-N({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid246.0921246.005825762-1.573isopentenyl-diphosphate0-2FDB0225693-methyl-3-butenyl pyrophosphate;Delta3-isopentenyl diphosphate;Delta3-methyl-3-butenyl diphosphate;Diphosphoric acid mono(3-methyl-3-butenyl) ester;Ipp;Ipr;Isopentenyl diphosphate;Isopentenyl pyrophosphate;Isopentenyl-pp;Mono(3-methyl-3-butenyl) diphosphate;Delta(3)-isopentenyl-pp;Delta-3-isopentenyl pyrophosphat;3-methylbut-3-en-1-yl trihydrogen diphosphate;3-methylbut-3-enyl phosphono hydrogen phosphate;Delta-3-isopentenyl pyrophosphate;Ippp;3-methyl-3-butenyl pyrophosphoric acid;Isopentenyl diphosphoric acid;3-methylbut-3-en-1-yl trihydrogen diphosphoric acid;3-methylbut-3-enyl phosphono hydrogen phosphoric acid;Delta-3-isopentenyl pyrophosphoric acid;δ-3-isopentenyl pyrophosphate;δ-3-isopentenyl pyrophosphoric acid;Delta3-isopentenyl diphosphoric acid;δ3-isopentenyl diphosphate;δ3-isopentenyl diphosphoric acid;Delta3-methyl-3-butenyl diphosphoric acid;δ3-methyl-3-butenyl diphosphate;δ3-methyl-3-butenyl diphosphoric acid;Diphosphate mono(3-methyl-3-butenyl) ester;Isopentenyl pyrophosphoric acid;Mono(3-methyl-3-butenyl) diphosphoric acidPW_C001039IsopPyr8055830215498730719876061608281210123102251235224978923111121475122124033135874DimethylallylpyrophosphateHMDB0001120Dimethylallylpyrophosphate, also known as 2-isopentenyl diphosphate or delta-prenyl diphosphate, belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Dimethylallylpyrophosphate exists as a solid, slightly soluble (in water), and a moderately acidic compound (based on its pKa). Dimethylallylpyrophosphate has been found in human muscle tissue. Within the cell, dimethylallylpyrophosphate is primarily located in the peroxisome, cytoplasm and mitochondria. Dimethylallylpyrophosphate exists in all living organisms, ranging from bacteria to humans. In humans, dimethylallylpyrophosphate is involved in the lovastatin action pathway, the desmosterolosis pathway, the risedronate action pathway, and the ibandronate action pathway. Dimethylallylpyrophosphate is also involved in several metabolic disorders, some of which include the wolman disease pathway, the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the mevalonic aciduria pathway, and the child syndrome pathway. Outside of the human body, dimethylallylpyrophosphate can be found in a number of food items such as ucuhuba, yellow wax bean, white cabbage, and european plum. This makes dimethylallylpyrophosphate a potential biomarker for the consumption of these food products. Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. (wikipedia).358-72-5C0023564716057CPD-4211627DB01785CC(C)=CCO[P@](O)(=O)OP(O)(O)=OC5H12O7P2InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)CBIDRCWHNCKSTO-UHFFFAOYSA-N({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid246.0921246.005825762-1.583dimethylallyl diphosphate0-2FDB0224341,1-dimethyl-4-phenylpiperazinium iodide;2-isopentenyl diphosphate;3,3-dimethylallyl pyrophosphate;3-methyl-2-buten-1-ol pyrophosphate;3-methyl-2-buten-1-ol trihydrogen pyrophosphate;3-methyl-2-butenyl pyrophosphate;3-methylbut-2-enyl pyrophosphate;Dmapp;Dmpp;Delta2-isopentenyl diphosphate;Delta2-isopentenyl-diphosphate;Dimethylallyl diphosphate;Dimethylallyl pyrophosphate;Dimethylallyl-pp;Dimethylallyl-ppi;Dimethylallyl-diphosphate;Dimethylallyl-pyrophosphate;Dimethylallylpyrophosphate;Diphosphoric acid mono(3-methyl-2-butenyl) ester;Ipe;Prenyl diphosphate;Prenyl-diphosphate;Delta-prenyl diphosphate;Monoprenyl diphosphate;2-isopentenyl diphosphoric acid;Dimethylallylpyrophosphoric acid;Delta2-isopentenyl diphosphoric acid;δ2-isopentenyl diphosphate;δ2-isopentenyl diphosphoric acid;Dimethylallyl pyrophosphoric acid;Monoprenyl diphosphoric acid;Prenyl diphosphoric acidPW_C000874Ipe81057309216123112251248815178924334121477408124035374423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-Nmagnesium(2+) ion24.30523.9850418980magnesium(2+) ion22FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+868227426816476272726811581918883229363998339922111674614834915294317641421241024115929422331262933737454031477491486954497456525310453291115356112537610359061475934151603815560941616250166648417865941646881160697919971702057194206722721372332117250214731021673131987473222117631321184321012312225123242491251328812581226127292901527528515337308771371337723632977937336783933347841733578489115785223317853635678574130800203688004518480048372806231188065413580865158096525381841519383238394900271085962231105593901156873981199744061200701221202473821207024071209814081211811241212654291213194191219241251220864051224084221227591201229213991233071191235463741238354641238894551244771361246373761249783751254472971255984841256694791257774811259214821259472991259734951260004901262434781265534911267533001271253891271645011273805021274073881274515071278042091281255081283473951170Flavin MononucleotideHMDB0001520Flavin mononucleotide (FMN), or riboflavin-5?-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. Flavin mononucleotide is also used as an orange-red food colour additive. It is the principal form in which riboflavin is found in cells and tissues.146-17-8C0006164397617621FMN559060DB03247CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2C17H21N4O9PInChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1FVTCRASFADXXNN-SCRDCRAPSA-N{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid456.3438456.104614802-2.836riboflavin 5'-phosphate0-3FDB001984Fmn;Flanin;Flavine mononucleotide;Flavol;Riboflavin;Riboflavin 5'-monophosphate;Riboflavin 5'-phosphate;Riboflavin mononucleotide;Riboflavin monophosphate;Riboflavin phosphate;Riboflavin-5'-phosphate na;Riboflavin-5-phosphate;Riboflavine 5'-monophosphate;Riboflavine 5'-phosphate;Riboflavine dihydrogen phosphate;Riboflavine monophosphate;Riboflavine phosphate;Riboflavine-5'-phosphate;Vitamin b2 phosphate;Flavin mononucleotide;Riboflavin 5'-(dihydrogen phosphate)PW_C001170FlvnMnt539811901416922496131577210111900211123132257751911577590111787301321204334051204541221219291241230673761230881351244821181256982971261042991271902051273122091276863881144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid665.441665.124771695-2.358NADH0-2FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH14341533490864810111521275514695422304927811728362931099480618481218482128490464959315169955240103533211153581125466123547912555931355698100573710858291415915147594515160271556079161638716472178677111768931607011188709916371722057195206746222282442268360225908622411809198118212161232024913003298130153001325522342403322426183157710713277123133772081347737133177651336776683347770033277707130779171137798634780009368806911199382212411054938811285494115838118119955406120172407120378122120986408121162425121244126121693429121818383122616384122745120123127447123138136123551374123734460123814443124242464124371398125189121125345479125531481125762297125808299125926482126516495126767480126888501127385502128090390128362391128429395993Geranyl-PPHMDB0001285Geranyl diphosphate is the precursor of monoterpenes, a large family of natural occurring C10 compounds predominately found in plants and animals. Geranyl diphosphate is regarded as a key intermediate in the steroid, isoprene and terpene biosynthesis pathways and is used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids. (wikipedia). In humans, geranyl diphosphate synthase (GPPS) catalyzes the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl diphosphate. Animals produce IPP through the mevalonate (MVA) pathway. Isoprenoid compounds have been implicated in several human disease states including coronary heart disease, blindness, infectious hepatitis and cancer. Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia.763-10-0C0034144599517211GERANYL-PP393471DB02552CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)OC10H20O7P2InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+GVVPGTZRZFNKDS-JXMROGBWSA-N[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid314.2091314.068426018-2.543geranyl diphosphate0-2FDB001463(2e)-3,7-dimethylocta-2,6-dien-1-yl trihydrogen diphosphate;Geranyl diphosphate;Geranyl-pp;Geranyl-diphosphate;Geranyl-pyrophosphate;Monoterpenyl diphosphate;Neryl diphosphate;Trans-geranyl pyrophosphate;Polyisopentenylpyrophosphate;Polyisopentenyldiphosphate;Trans-polyisopentenyldiphosphate;Polyprenyl diphosphate;Polyisopentenylpyrophosphoric acid;Polyisopentenyldiphosphoric acid;Trans-polyisopentenyldiphosphoric acid;Polyprenyl diphosphoric acidPW_C000993Gryl-PP808515988731119876091608282210123142251521830678925111121479122124037135170PyrophosphateHMDB0000250The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.14000-31-8C0001364410218361PPI559142DB04160[O-]P([O-])(=O)OP([O-])([O-])=OO7P2InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4XPPKVPWEQAFLFU-UHFFFAOYSA-J(phosphonooxy)phosphonic acid173.9433173.9119253784pyrophosphoric acid0-3FDB021918(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ionPW_C000170Ppi122354638429237353288222121731620492410592815294175144868545034895252104529410154091175424103543311854581205548111555913255841335606135565510858791076239166697819970731887134163727216073121987318213827515182832101186916112002222120411641231522512323249125122881257922612695290152193061537518347601742561315426973187723532977317128776353367841633578928331791531127995013479958130800473728041717085630194786384948141259481938298678223110634391113270395113275389115527136115532399119934122120017124120032406120330410120936407121261429121341121121486383122407422122985444123502119123831464124044398124977375125324297125395299125410479125597484125656485125876481126552491126869205126935388126950501127337206128124508768Farnesyl pyrophosphateHMDB0000961Farnesyl pyrophosphate, also known as farnesyl diphosphoric acid or farnesyl-PP, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Farnesyl pyrophosphate is considered to be a practically insoluble (in water) and relatively neutral molecule. Farnesyl pyrophosphate has been found in human testicle tissue, and has also been primarily detected in blood. Farnesyl pyrophosphate can be found anywhere throughout the human cell, such as in membrane (predicted from logP), peroxisome, mitochondria, and endoplasmic reticulum. Farnesyl pyrophosphate exists in all living organisms, ranging from bacteria to humans. Farnesyl pyrophosphate participates in a number of enzymatic reactions. In particular, Ferroheme b and farnesyl pyrophosphate can be converted into heme O; which is mediated by the enzyme heme O synthase. Furthermore, Farnesyl pyrophosphate and isopentenyl pyrophosphate can be converted into octaprenyl diphosphate through the action of the enzyme octaprenyl diphosphate synthase. Furthermore, Farnesyl pyrophosphate can be biosynthesized from geranyl-PP and isopentenyl pyrophosphate through its interaction with the enzyme geranyl diphosphate synthase / farnesyl diphosphate synthase. Finally, Farnesyl pyrophosphate and isopentenyl pyrophosphate can be converted into di-trans,octa-cis-undecaprenyl diphosphate; which is catalyzed by the enzyme undecaprenyl diphosphate synthase. In humans, farnesyl pyrophosphate is involved in the simvastatin action pathway, the risedronate action pathway, the alendronate action pathway, and the ibandronate action pathway. Farnesyl pyrophosphate is also involved in several metabolic disorders, some of which include the hyper-igd syndrome pathway, the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the porphyria variegata (PV) pathway, and lysosomal acid lipase deficiency (wolman disease). Outside of the human body, farnesyl pyrophosphate can be found in a number of food items such as sweet basil, apple, spearmint, and nuts. This makes farnesyl pyrophosphate a potential biomarker for the consumption of these food products. Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia.372-97-4C0044844571317407FARNESYL-PP393270DB07780[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)CC15H28O7P2InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+VWFJDQUYCIWHTN-YFVJMOTDSA-N{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid382.33382.131027238-3.683[hydroxy([(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy)phosphoryl]oxyphosphonic acid0-2FDB022339(2e,6e)-farnesyl diphosphate;(2e,6e)-farnesyl pyrophosphate;(e,e)-farnesyl diphosphate;(e,e)-farnesyl pyrophosphate;(all-e)-farnesyl diphosphate;2-trans,6-trans-farnesyl diphosphate;2-trans,6-trans-farnesyl pyrophosphate;All-trans-farnesyl pyrophosphate;Farnesyl diphosphate;Farnesyl pyrophosphate;Farnesyl-pp;Trans-farnesyl pyrophosphate;Trans-trans-farnesyl diphosphate;Trans-trans-farnesyl pyrophosphate;(2e,6e)-farnesol diphosphate;Trans,trans-farnesyl diphosphate;(2e,6e)-farnesol diphosphoric acid;2-trans,6-trans-farnesyl diphosphoric acid;(2e,6e)-farnesyl diphosphoric acid;(2e,6e)-farnesyl pyrophosphoric acid;(all-e)-farnesyl diphosphoric acid;(e,e)-farnesyl pyrophosphoric acid;2-trans,6-trans-farnesyl pyrophosphoric acid;All-trans-farnesyl pyrophosphoric acid;Farnesyl diphosphoric acid;Farnesyl pyrophosphoric acid;Trans,trans-farnesyl diphosphoric acid;Trans-trans-farnesyl diphosphoric acidPW_C000768FarPP813516148374427047160731419882842101231622512319151786051327892611180968312148212212203940712404013512459311912619148117009(3E,6E)-α-FarneseneHMDB0036066(3E,6E)-alpha-Farnesene is found in apple. (3E,6E)-alpha-Farnesene is a constituent of the natural coating of apples and pears and other fruit. (3E,6E)-alpha-Farnesene is a flavouring ingredient.
(3E,6E)-alpha-Farnesene belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units.502-61-4C096655281516102804444849CC(C)=CCC\C(C)=C\C\C=C(/C)C=CC15H24InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+CXENHBSYCFFKJS-VDQVFBMKSA-N(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene204.3511204.187800768-4.600farnesene00C09665(3e,6e)-alpha-farnesene;-e,e-farnesene;-trans-farnesene;3,7,11-trimethyl-(e,e)-1,3,6,10-dodecatetraene;Alph;Alpha;Alpha-trans,trans-farnesene;Trans,trans-alpha-farnesene;(3e,6e)-a-farnesene;(3e,6e)-α-farnesene;A-farnesene;α-farnesenePW_C0170093E6EαF1233515157907(Z,E)-α-farnesene(Z,e)-alpha-Farnesene, also known as cis-α-farnesene or (Z,e)-α-farnesene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (Z,e)-alpha-Farnesene is considered to be a practically insoluble (in water) and relatively neutral molecule. Outside of the human body, (Z,e)-alpha-farnesene can be found in ceylon cinnamon. This makes (Z,e)-alpha-farnesene a potential biomarker for the consumption of this food product. A farnesene synthesized in farnesene biosynthesis.536288939238CPD-93384515350CC(C)=CCC\C(C)=C\C\C=C(\C)C=CC15H24InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10-,15-12+CXENHBSYCFFKJS-OXYODPPFSA-N(3Z,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene204.3511204.187800768-4.600(Z,E)-α-farnesene00Cis-alpha-farnesenePW_C057907ZEαF1233615157908(E)-β-FarneseneHMDB0062763(e)-beta-Farnesene, also known as b-farnesene or beta-trans-farnesene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (e)-beta-farnesene is considered to be a hydrocarbon lipid molecule (e)-beta-Farnesene is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, (e)-beta-farnesene is primarily located in the membrane (predicted from logP) and cytoplasm (e)-beta-Farnesene is also a parent compound for other transformation products, including but not limited to, beta-hexaprene, beta-heptaprene, and beta-geranylfarnesene. (E)-beta-farnesene is a farnesene synthesized in farnesene biosynthesis.18794-84-8C09666528151710418CPD-82394444850[H]\C(CCC(=C)C=C)=C(\C)CCC=C(C)CC15H24InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9,12H,1,4,7-8,10-11H2,2-3,5H3/b15-12+JSNRRGGBADWTMC-NTCAYCPXSA-N(6E)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene204.357204.187800773-4.780β-farnesene00trans-beta-Farnesene;trans-β-FarnesenePW_C057908EβF1233715111544isopentenyl diphosphate isomeraseQ38929Isopentenyl diphosphate isomerase is an enzyme in the chloroplast that catalyzes a reaction in the epoxysqualene biosynthesis and farnesene pathways whereby isopentenyl diphosphate is reversibly converted to dimethylallyl diphosphate. In Arabidopsis thaliana, isopentenyl diphosphate isomerase is encoded by 2 differentially expressed genes (IPP1, IPP2). This enzyme requires FAD, NAD(P)H, and a divalent cation (e.g. magnesium) as cofactors.IPP145.3.3.21229922511545geranylpyrophosphate synthaseQ5HZ00Geranylpyrophosphate synthase is an enzyme in the chloroplast that catalyzes a reaction in both epoxysqualene and farnesene biosynthesis pathways whereby dimethylallyl diphosphate is converted into geranyl diphosphate. It requires magnesium ion as a cofactor. GPPS42.5.1.11230122513667222411546(2E,6E)-farnesyl diphosphate synthaseQ09152(2E,6E)-farnesyl diphosphate synthase is an enzyme found in the cytosol, chloroplast, and mitochondria that catalyzes a reaction in both the epoxysqualene biosynthesis and farnesene biosynthesis pathways whereby geranyl diphosphate is converted into farnesyl diphosphate. In Arabidopsis thaliana, there appears to be several different enzymes could catalyze this reaction, each encoded by differentially expressed genes.FPS142.5.1.1012303151123042251230522213667622411549farnesyl diphosphate transporterZ0Z000Farnesyl diphosphate transporter is predicted to transport farnesyl diphosphate out of the chloroplast and into the cytosol.?41231722511550(E,E)-alpha-farnesene synthaseA4FVP2(E,E)-alpha-farnesene synthase is an enzyme in the cytosol that catalyzes a reaction in the farnesene biosynthesis pathway whereby farnesyl diphosphate is converted into (E,E)-alpha-farnesene. In Arabidopsis thaliana, (E,E)-alpha-farnesene synthase is encoded by 2 differentially expressed genes (TPS02, TPS03). It requires a magnesium or manganese ion as cofactors.TPS0344.2.3.46; 4.2.3.106123291512547416413659722511551(Z,E)-alpha-farnesene synthaseZ0Z000(Z,E)-alpha-farnesene synthase is a predicted enzyme in the cytosol that is theorized to catalyze a reaction in the farnesene biosynthesis pathway whereby farnesyl diphosphate is converted into (Z,E)-alpha-farnesene.?44.2.3.-1233115111552sesquiterpene synthaseQ4KSH9Sesquiterpene synthase is an enzyme in the cytosol that catalyzes many reactions including a reaction in the farnesene biosynthesis pathway whereby farnesyl diphosphate is converted into (E)-beta-farnesene. It requires a magnesium or manganese ion as a cofactor.AT5G4463044.2.3.47; 4.2.3.69; 4.2.3.78; 4.2.3.79123331511366122201366202935422isopentenyl diphosphate isomerase4PW_P005422127761154468042368111706821144123002255423geranylpyrophosphate synthase4PW_P0054231277711545683423123022255424(2E,6E)-farnesyl diphosphate synthase4PW_P00542412778115465427farnesyl diphosphate transporter4PW_P0054271278111549123182255428(E,E)-alpha-farnesene synthase/(E)-beta-ocimene synthase4PW_P0054281278211550686423123301511365962255429(Z,E)-alpha-farnesene synthase4PW_P0054291278311551123321515430sesquiterpene synthase4PW_P00543012784115526874231233415147526PW_R047526Both14692210391Compoundfalse1469238741Compoundfalse3767054225.3.3.247527PW_R047527Both1469248741Compoundfalse14692510391Compoundfalse1469269931Compoundfalse1469271701Compoundfalse3767154232.5.1.147528PW_R047528Right1469289931Compoundfalse14692910391Compoundfalse1469307681Compoundfalse1469311701Compoundtrue3767254242.5.1.1047531PW_R047531Right1469447681Compoundfalse1469451701Compoundfalse146946170091Compoundfalse3767554284.2.3.4647532PW_R047532Right1469477681Compoundfalse146948579071Compoundfalse1469491701Compoundfalse3767654294.2.3.-47533PW_R047533Right1469507681Compoundfalse146951579081Compoundfalse1469521701Compoundfalse3767754304.2.3.47896PW_T00089610487681Compound225151Right79654272017-02-23T15:12:18-07:002017-02-23T15:12:18-07:0022541997310392253false60644310regular1001104199748742253false105644810regular1001004199754232259false82645010regular1002541997611702259false82642010regular1003541997711442259false82640010regular1002541997810392253false110128810regular1001104199799932253false150144910regular10010041998017022545false144935910regular63434199814232259false127644810regular1002541998210392253false155628910regular1001104199837682253false195144310regular10011041998417022545false189935810regular63434199857681513false1951112310regular10011041999617015145false144478510regular6343419997170091513false135186310regular1001104199984231519false157687010regular10025419999579071513false1351112410regular10011042000017015145false1444103410regular6343420001579081513false1351136910regular10010042000217015145false1444128410regular63434200034231519false1576137510regular10025251100115442252false8014658subunitregular15070251101115452252false12514638subunitregular15070251102115462252false17064668subunitregular150702511051154976false19265888subunitregular15070251106115501512false15518858subunitregular150702511071155115198false155111438subunitregular15070251108115521512false155113908subunitregular150701436855422126662252502932511005036419975648155Cofactor5037419976648156Cofactor5038419977648157Cofactor1436865423126662252502942511015039419981648162Cofactor1436875424126662252502952511021436905427126662502982511051436915428126661512502992511065042419998648187Cofactor1436925429126661512503002511071436935430126661512503012511085043420003648194Cofactor648153M706 498 C736 498 771 500 801 500 5false18trueM 643.9468550441649 298.261556296296 L 629 297 L 635.3808877211858 310.5751343230783false648154M1056 498 C1026 498 981 500 951 500 5false18trueM 643.9468550441649 298.261556296296 L 629 297 L 635.3808877211858 310.5751343230783false648155M811 350.5 L811 400.5 L861 350.5 z10true18648156M811 320.5 L811 370.5 L861 320.5 z10true18648157M811 300.5 L811 350.5 L861 300.5 z10true18648158M1156 498 C1186 498 1221 498 1251 498 5false18trueM 474.94685504416486 398.261556296296 L 460 397 L 466.38088772118584 410.5751343230783false648159M1201 343 C1202 451 1221 498 1251 498 5false18trueM 474.94685504416486 398.261556296296 L 460 397 L 466.38088772118584 410.5751343230783false648160M1501 499 C1471 499 1431 498 1401 498 5false18trueM 474.94685504416486 398.261556296296 L 460 397 L 466.38088772118584 410.5751343230783false648161M1449 380.5 C1447 458.5 1431 498 1401 498 5false18trueM 474.94685504416486 398.261556296296 L 460 397 L 466.38088772118584 410.5751343230783false648162M1446 773 L1446 823 L1496 773 z10true18648163M1601 499 C1631 499 1676 501 1706 501 5false18648164M1656 344 C1656 451 1676 501 1706 501 5false18trueM 1890.0096189432334 860.5 L 1903 853 L 1890.0096189432334 845.5false648165M1951 498 C1921 498 1886 501 1856 501 5false18trueM 969.9468550441649 398.261556296296 L 955 397 L 961.3808877211858 410.5751343230783false648166M1899 379.5 C1900 462.5 1886 501 1856 501 5false18trueM 969.9468550441649 398.261556296296 L 955 397 L 961.3808877211858 410.5751343230783false648181M2001 553 C2001 583 2001 558 2001 588 83false18trueM 2190.5 927.0096189432334 L 2198 940 L 2205.5 927.0096189432334false648182M2001 1123 C2001 1093 2001 688 2001 658 83false18trueM 1566.9468550441647 398.261556296296 L 1552 397 L 1558.380887721186 410.5751343230783false648183M606 498 C576 498 481 498 451 498 5false18trueM 790.0096189432334 857.5 L 803 850 L 790.0096189432334 842.5false648184M1951 1178 C1921 1178 1883 1178 1853 1178 C1851 1137 1854 990 1852 923 C1805 922 1745 920 1701 920 5false18trueM 1713.9903810567666 994.5 L 1701 1002 L 1713.9903810567666 1009.5false648185M1507 806.5 C1506 878.5 1521 920 1551 920 5false18trueM 1179.9468550441647 538.261556296296 L 1165 537 L 1171.380887721186 550.5751343230784false648186M1451 923 C1481 923 1521 920 1551 920 5false18trueM 1179.9468550441647 538.261556296296 L 1165 537 L 1171.380887721186 550.5751343230784false648187M1746 1130.5 L1746 1180.5 L1796 1130.5 z10true18648188M1951 1178 C1921 1178 1731 1178 1701 1178 5false18trueM 1713.9903810567666 1197.5 L 1701 1205 L 1713.9903810567666 1212.5false648189M1451 1179 C1481 1179 1521 1178 1551 1178 5false18trueM 1094.9468550441647 538.261556296296 L 1080 537 L 1086.380887721186 550.5751343230784false648190M1507 1055.5 C1507 1140.5 1521 1178 1551 1178 5false18trueM 1094.9468550441647 538.261556296296 L 1080 537 L 1086.380887721186 550.5751343230784false648191M1951 1178 C1921 1178 1890 1178 1852 1177 C1852 1277 1851 1377 1852 1425 C1815 1425 1753 1424 1701 1425 5false18trueM 1713.843775548577 1444.2516176102508 L 1701 1452 L 1714.1321837620471 1459.2488447106987false648192M1451 1424 C1481 1424 1521 1425 1551 1425 5false18trueM 1094.9468550441647 638.261556296296 L 1080 637 L 1086.380887721186 650.5751343230784false648193M1507 1305.5 C1506 1382.5 1521 1425 1551 1425 5false18trueM 1094.9468550441647 638.261556296296 L 1080 637 L 1086.380887721186 650.5751343230784false648194M1746 1165.5 L1746 1215.5 L1796 1165.5 z10true181551371266647526225578767419973648153Left578768419974648154Right116235376701436851551381266647527225578769419974648158Left578770419978648159Left578771419979648160Right578772419980648161Right116236376711436861551391266647528225578773419979648163Left578774419982648164Left578775419983648165Right578776419984648166Right116237376721436871551421266647531151578787419985648184Left578788419996648185Right578789419997648186Right116240376751436911551431266647532151578790419985648188Left578791419999648189Right578792420000648190Right116241376761436921551441266647533151578793419985648191Left578794420001648192Right578795420002648193Right11624237677143693203128961266641119419983648181Left41120419985648182Right199541436907963813445612666217false30146316regular2174419973648183Right215475087891.01.0-33029154349753311M252.6666259765625 624 C320.6666259765625 621 2093.6666259765625 623 2154.6666259765625 625 237false60.00.053312M252.3333282470703 723.6666870117188 C306.3333282470703 723.6666870117188 2094.3333282470703 722.6666870117188 2154.3333282470703 723.6666870117188 237false60.00.053314M125 225 C125 175 175 125 225 125 C817 125 1585 125 2177 125 C2227 125 2277 175 2277 225 C2277 612 2277 1114 2277 1501 C2277 1551 2227 1601 2177 1601 C1585 1601 817 1601 225 1601 C175 1601 125 1551 125 1501 C125 1114 125 612 125 225 1true62152.01476.02151215Chloroplast Inner Membrane262589201.01.0160152151315Chloroplast Outer Membrane262684201.01.0160152151415Stroma267289201.01.0160152151715Cytosol997874201.01.01601520646539886252249215675041#EBFFEB41904501