7722-84-1
CAS
439161
PubChem-compound
C00430
KEGG Compound
937
ChemSpider
1.0
CHEBI:16134
ChEBI
UROPORPHYRIN_III
BioCyc
COPROPORPHYRINOGEN_I
BioCyc
29936
PubChem-compound
P40012
UniProt
HMDB0003125
HMDB
HMDB0002158
HMDB
439153
PubChem-compound
SMILES
CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(C=C)=C3C)N2)N1
HYDROXYMETHYLBILANE
BioCyc
C00448
KEGG Compound
Protoporphyrin IX
Uroporphyrinogen III
607-14-7
CAS
Unknown
1.0
1146
ChemSpider
CHEBI:15380
ChEBI
NADH
PW002462
PathWhiz
C25H40N7O19P3S
Succinyl-CoA
867.1312
CHEBI:17200
ChEBI
952
ChemSpider
ALPHA-GLUCOSE-16-BISPHOSPHATE
BioCyc
ReactionCatalysis6598
ACTIVATION
ReactionCatalysis6597
ACTIVATION
ReactionCatalysis6596
ACTIVATION
HMDB0001086
HMDB
ReactionCatalysis6599
ACTIVATION
UDP-GLUCURONATE
BioCyc
6031
PubChem-compound
PW000157
PathWhiz
1.0
CHEBI:16240
ChEBI
1.0
445713
PubChem-compound
1.0
Saccharomyces cerevisiae
27815
ChemSpider
Fe2+
Uridine 5'-diphosphate
531-14-6
CAS
CHEBI:27484
ChEBI
HMDB0001097
HMDB
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O
C45H52N4O18
Bilirubin diglucuronide
936.32764
389645
ChemSpider
C40H38N4O16
Uroporphyrin I
830.2283
389644
ChemSpider
C15H22N2O18P2
Uridine diphosphate glucuronic acid
580.0343
C00237
KEGG Compound
C36H38N4O8
Coproporphyrin I
654.269
389649
ChemSpider
C34H40N4O4
Protoporphyrinogen IX
568.30493
Cytosol
CHEBI:17381
ChEBI
1.0
BILIRUBIN
BioCyc
1.0
SubPathwayInteraction3719
SubPathwayReaction
SubPathway3719Reaction
C00007
KEGG Compound
1.0
C00001
KEGG Compound
C00004
KEGG Compound
CHEBI:17033
ChEBI
C00003
KEGG Compound
C00486
KEGG Compound
Protoporphyrin IX
114-25-0
CAS
Protoporphyrinogen IX
HMDB0003178
HMDB
1.0
C21H28N7O14P2
NAD
664.11694
C00011
KEGG Compound
HMDB0000902
HMDB
CHEBI:17245
ChEBI
C00015
KEGG Compound
C00014
KEGG Compound
Oxygen
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C5/C=C6\N=C(\C=C\1/N\2[Fe]N45)C(C)=C6C=C)/C(CCC(O)=O)=C3C
1.16.3.1
false
1.16.3.1
4 Fe2+ + 4 Hydrogen + Oxygen ← 4 Fe3+ + 2 Water
RIGHT_TO_LEFT
4.99.1.1
false
4.99.1.1
Fe2+ + Protoporphyrin IX → Heme + 2 Hydrogen
LEFT_TO_RIGHT
2.5.1.-
false
2.5.1.-
Farnesyl pyrophosphate + Heme → Heme O
LEFT_TO_RIGHT
Reaction6648
false
Heme O → Heme A
LEFT_TO_RIGHT
1.14.99.3
false
1.14.99.3
3 AH2 + Heme + 3 Oxygen → 3 A + Biliverdin + Carbon monoxide + Fe2+ + 3 Water
LEFT_TO_RIGHT
5-Aminolevulinic acid
4.2.1.75
false
4.2.1.75
Hydroxymethylbilane → Uroporphyrinogen III + Water
LEFT_TO_RIGHT
4.1.1.37
false
4.1.1.37
Uroporphyrinogen I → 4 Carbon dioxide + Coproporphyrinogen I
LEFT_TO_RIGHT
HMDB0004158
HMDB
4.1.1.37
false
4.1.1.37
Uroporphyrinogen III → 4 Carbon dioxide + Coproporphyrinogen III
LEFT_TO_RIGHT
1.3.3.3
false
1.3.3.3
Coproporphyrinogen III + 2 Hydrogen + Oxygen → 2 Carbon dioxide + Protoporphyrinogen IX + 2 Water
LEFT_TO_RIGHT
1.0
1.3.3.4
false
1.3.3.4
3 Oxygen + Protoporphyrinogen IX → 3 Hydrogen peroxide + Protoporphyrin IX
LEFT_TO_RIGHT
CHEBI:17499
ChEBI
388307
ChemSpider
C40H44N4O16
Uroporphyrinogen III
836.2752
18273-06-8
CAS
CPD-10134
BioCyc
C40H38N4O16
Uroporphyrin III
830.2283
C36H44N4O8
Coproporphyrinogen III
660.3159
Heme
Protoporphyrinogen IX
53-84-9
CAS
HMDB0000916
HMDB
C00027
KEGG Compound
Transport10334
false
Protoporphyrin IX (→) Transport: Saccharomyces cerevisiae, Cell, Mitochondrial Outer Membrane to Saccharomyces cerevisiae, Cell, Mitochondrial Matrix
LEFT_TO_RIGHT
553-12-8
CAS
2.3.1.37
false
2.3.1.37
Glycine + Succinyl-CoA → 5-Aminolevulinic acid + Carbon dioxide
LEFT_TO_RIGHT
4.2.1.24
false
4.2.1.24
5-Aminolevulinic acid → Porphobilinogen + 2 Water
LEFT_TO_RIGHT
1.0
2.5.1.61
false
2.5.1.61
4 Porphobilinogen + Water → 4 Ammonia + Hydroxymethylbilane
LEFT_TO_RIGHT
1.0
Uroporphyrinogen I
3.0
Fe
Fe2+
55.93494
73023-76-4
CAS
372-97-4
CAS
C00032
KEGG Compound
Uroporphyrin III
C00037
KEGG Compound
CHEBI:18276
ChEBI
SMILES
NC(=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]1O
Hydrogen peroxide
4.0
C00282
KEGG Compound
4.0
CHEBI:18392
ChEBI
HYDROGEN-PEROXIDE
BioCyc
AH2
C33H34N4O6
Biliverdin
582.24786
4.0
C02469
KEGG Compound
767
ChemSpider
C00167
KEGG Compound
Alcohol
1.0
763
ChemSpider
604-98-8
CAS
762
ChemSpider
C9H14N2O12P2
Uridine 5'-diphosphate
404.0022
1.3.1.24
false
1.3.1.24
Biliverdin + NAD → Bilirubin + NADH
LEFT_TO_RIGHT
2.4.1.17
false
2.4.1.17
Bilirubin + Uridine diphosphate glucuronic acid → Bilirubin diglucuronide + Uridine 5'-diphosphate
LEFT_TO_RIGHT
3.2.1.31
false
3.2.1.31
Bilirubin diglucuronide + Water → Alcohol + Urobilinogen
LEFT_TO_RIGHT
C15H28O7P2
Farnesyl pyrophosphate
382.13104
784
PubChem-compound
C40H46N4O17
Hydroxymethylbilane
854.28577
C15672
KEGG Compound
788
PubChem-compound
C15670
KEGG Compound
C01024
KEGG Compound
Heme A
7732-18-5
CAS
BILIRUBIN-BISGLUCURONOSIDE
BioCyc
Coproporphyrin I
315
ChemSpider
HMDB0001487
HMDB
PROTOPORPHYRINOGEN
BioCyc
17208-65-0
CAS
AMMONIA
BioCyc
SMILES
N
HMDB0001008
HMDB
C5H9NO3
5-Aminolevulinic acid
131.05824
Transport536
false
Coproporphyrinogen III (→) Transport: Saccharomyces cerevisiae, Cell, Cytosol to Saccharomyces cerevisiae, Cell, Mitochondrion
LEFT_TO_RIGHT
CHEBI:29033
ChEBI
Heme
Transport538
false
Heme (→) Transport: Saccharomyces cerevisiae, Cell, Mitochondrial Matrix to Saccharomyces cerevisiae, Cell, Cytosol
LEFT_TO_RIGHT
2.0
HMDB0001362
HMDB
HMDB0002211
HMDB
CHEBI:29034
ChEBI
HMDB0001361
HMDB
16522
ChemSpider
Fe
Fe3+
55.93494
Porphobilinogen
5353439
PubChem-compound
NAD
56-40-6
CAS
Bilirubin diglucuronide
4.0
SMILES
CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1
FARNESYL-PP
BioCyc
630-08-0
CAS
SMILES
OC(=O)CCC1=C2CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3
HMDB0001377
HMDB
Coproporphyrinogen III
HMDB0001137
HMDB
SMILES
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O
A
SMILES
NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1
1.0
962
PubChem-compound
UROPORPHYRINOGEN-III
BioCyc
C05767
KEGG Compound
121893
PubChem-compound
58-98-0
CAS
C05766
KEGG Compound
1.0
C05769
KEGG Compound
C34H32FeN4O4
Heme
616.1773
Unknown
CO2
Carbon dioxide
43.98983
C05768
KEGG Compound
Coproporphyrinogen III
C05770
KEGG Compound
HMDB0003325
HMDB
730
ChemSpider
SMILES
O=O
HMDB0001149
HMDB
2.0
C01051
KEGG Compound
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)C1=C2C=C3C(C)=C(C=C)C4=[N]3[Fe++]35N6C(=C4)C(C)=C(CCC(O)=O)C6=CC4=[N]3C(=CC(N25)=C1C)C(C=O)=C4CCC(O)=O
HMDB0000051
HMDB
HMDB0001261
HMDB
HMDB0002111
HMDB
HMDB0000295
HMDB
5809
ChemSpider
HMDB0001022
HMDB
HMDB0000054
HMDB
1.0
C00091
KEGG Compound
4.0
C36H44N4O8
Coproporphyrinogen I
660.3159
4932
TAXONOMY
C36H38N4O8
Coproporphyrin III
654.269
C05787
KEGG Compound
Glycine
SubPathwayOutput
995
ChemSpider
C05791
KEGG Compound
H2O
Water
18.010565
H2O2
Hydrogen peroxide
34.005478
SMILES
NCC(O)=O
HMDB0001162
HMDB
1867-62-5
CAS
NADH
BioCyc
NAD
BioCyc
Protoporphyrinogen oxidase
15438-31-0
CAS
Farnesyl pyrophosphate
1.0
1.0
1.0
UROPORPHYRIN_I
BioCyc
977
PubChem-compound
31110-56-2
CAS
25394
ChemSpider
1.0
C01079
KEGG Compound
2.0
5-AMINO-LEVULINATE
BioCyc
C03263
KEGG Compound
1.0
10469486
ChemSpider
1.0
COPROPORPHYRINOGEN_III
BioCyc
SMILES
[H][H]
Carbon monoxide
SMILES
[C-]#[O+]
16736727
ChemSpider
16736725
ChemSpider
SMILES
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C
134
ChemSpider
SMILES
O
SMILES
OO
H3N
Ammonia
17.026548
Coproporphyrinogen I
58838673
PubChem-compound
BILIVERDINE
BioCyc
C33H36N4O6
Bilirubin
584.2635
2616-64-0
CAS
Protoporphyrin IX
393270
ChemSpider
C40H44N4O16
Uroporphyrinogen I
836.2752
C02191
KEGG Compound
1.0
5280352
PubChem-compound
3571849
ChemSpider
CHEBI:15846
ChEBI
C10H14N2O4
Porphobilinogen
226.09535
2.0
C34H34N4O4
Protoporphyrin IX
562.258
16736701
ChemSpider
SMILES
[Fe++]
GO:0005829
GENE ONTOLOGY
275
ChemSpider
274
ChemSpider
Ferric-Hydroxamate-Complexes
BioCyc
4510089
ChemSpider
CHEBI:16908
ChEBI
137
PubChem-compound
Ammonia
SMILES
CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C2\NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O
1021
PubChem-compound
137397-56-9
CAS
7412-77-3
CAS
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
Coproporphyrin III
Mitochondrion
Porphyrin Metabolism
1.0
1.0
GLY
BioCyc
Carbon dioxide
27284
PubChem-compound
CPD-6641
BioCyc
321
PubChem-compound
217
ChemSpider
58-68-4
CAS
108741
ChemSpider
Water
CHEBI:24480
ChEBI
Oxygen
124-38-9
CAS
C2H5NO2
Glycine
75.03203
Fe2+
HMDB0000570
HMDB
HMDB0000692
HMDB
4.0
3.0
1.0
1.0
635-65-4
CAS
1.0
Heme O
5257127
PubChem-compound
GO:0005759
GENE ONTOLOGY
17473
PubChem-compound
Hydrogen
7664-41-7
CAS
1.0
Glycine and Serine Metabolism
SubPathway
Hydroxymethylbilane
CO
Carbon monoxide
27.994915
Succinyl-CoA
H2
Hydrogen
2.01565
C00931
KEGG Compound
4444055
ChemSpider
Reaction1879
false
Hydroxymethylbilane → Uroporphyrinogen I
LEFT_TO_RIGHT
1.0
SMILES
O=C=O
SMILES
CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=O
CHEBI:27609
ChEBI
222
PubChem-compound
C21H29N7O14P2
NADH
665.12476
Reaction1877
false
Uroporphyrinogen III → Uroporphyrin III
LEFT_TO_RIGHT
1.0
GO:0005741
GENE ONTOLOGY
17459-92-6
CAS
SMP0002363
SMPDB
16736509
ChemSpider
Protoporphyrinogen oxidase
1.0
Hydrogen
HMDB0000123
HMDB
SMILES
CC1=C2CC3=C(CCC(O)=O)C(C)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3
1.0
HMDB0000245
HMDB
GO:0005739
GENE ONTOLOGY
HMDB0006901
HMDB
3.0
PORPHOBILINOGEN
BioCyc
Biliverdin
HMDB0000241
HMDB
Heme O
Mitochondrial Outer Membrane
TransportCatalysis1601
ACTIVATION
TransportCatalysis1600
ACTIVATION
CHEBI:17627
ChEBI
A
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
3.0
Urobilinogen
Protoporphyrin IX
5682
ChemSpider
UDP
BioCyc
440784
PubChem-compound
CHEBI:28766
ChEBI
14643-66-4
CAS
14875-96-8
CAS
CHEBI:15439
ChEBI
SMP0000004
SMPDB
Mitochondrial Matrix
ReactionCatalysis6611
ACTIVATION
ReactionCatalysis6610
ACTIVATION
SMILES
OC(=O)CCC1=C2CC3=C(CCC(O)=O)C(CC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3
AH2
SMILES
OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4CC(O)=O)/C(CC(O)=O)=C3CCC(O)=O
HMDB0000936
HMDB
SMILES
CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3
HMDB0000935
HMDB
440776
PubChem-compound
440775
PubChem-compound
Carbon dioxide
Fe3+
2.0
Reaction1886
false
Coproporphyrinogen III → Coproporphyrin III
LEFT_TO_RIGHT
Reaction1884
false
Uroporphyrinogen I → Uroporphyrin I
LEFT_TO_RIGHT
57560-10-8
CAS
Reaction1883
false
Coproporphyrinogen I → Coproporphyrin I
LEFT_TO_RIGHT
5459911
PubChem-compound
3.0
1976-85-8
CAS
106-60-5
CAS
1.0
CHEBI:16990
ChEBI
388299
ChemSpider
Uridine diphosphate glucuronic acid
O2
Oxygen
31.98983
C49H56FeN4O6
Heme A
852.3549
1.0
Water
CHEBI:15436
ChEBI
CHEBI:16645
ChEBI
CHEBI:15435
ChEBI
HMDB0012943
HMDB
CHEBI:16526
ChEBI
CHEBI:15437
ChEBI
487-90-1
CAS
CHEBI:28607
ChEBI
HEME_O
BioCyc
C00500
KEGG Compound
CHEBI:15430
ChEBI
7782-44-7
CAS
1.0
HMDB0000961
HMDB
Unknown
CHEBI:15428
ChEBI
1.0
HEME_A
BioCyc
1333-74-0
CAS
C49H58FeN4O5
Heme O
838.3757
CHEBI:17549
ChEBI
4573640
ChemSpider
Uroporphyrin I
SMILES
OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1
1179
PubChem-compound
281
PubChem-compound
5893
PubChem-compound
SMILES
[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C
Alcohol
CHEBI:30879
ChEBI
SMILES
NCC(=O)CCC(O)=O
3.0
SMILES
[Fe+3]
CHEBI:15377
ChEBI
CHEBI:15379
ChEBI
Unknown
20074-52-6
CAS
CHEBI:13193
ChEBI
Bilirubin
Oxygen
280
PubChem-compound
PROTOPORPHYRIN_IX
BioCyc
CHEBI:17407
ChEBI
1.0
SMILES
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3C
SMILES
CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3
SMILES
CC1=C(C=C)\C(NC1=O)=C/C1=C(C)C(CCC(=O)O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)=C(CC2=C(CCC(=O)O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C(C)=C(N2)\C=C2\NC(=O)C(C=C)=C2C)N1
SMILES
OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
C33H42N4O6
Urobilinogen
590.3104
C14819
KEGG Compound
1.0
C14818
KEGG Compound
3-METHYLBENZYLSUCCINYL-COA
BioCyc
CHEBI:28421
ChEBI
24604415
ChemSpider
CHEBI:17659
ChEBI
HMDB0001967
HMDB
1.0
2624-63-7
CAS
ReactionCatalysis6606
ACTIVATION
ReactionCatalysis6605
ACTIVATION
ReactionCatalysis6604
ACTIVATION
ReactionCatalysis6603
ACTIVATION
HMDB0000643
HMDB
ReactionCatalysis6609
ACTIVATION
ReactionCatalysis6608
ACTIVATION
ReactionCatalysis6607
ACTIVATION
ReactionCatalysis6602
ACTIVATION
ReactionCatalysis6601
ACTIVATION
ReactionCatalysis6600
ACTIVATION