C10H14N5O7P
3'-AMP
347.06308
389566
ChemSpider
20380-11-4
CAS
Cholesterol 25-hydroxylase
C27H46O4
3a,7a,12a-Trihydroxy-5b-cholestan-26-al
434.3396
CHEBI:16496
ChEBI
CHEBI:18431
ChEBI
HMDB0002159
HMDB
1.0
439153
PubChem-compound
474-73-7
CAS
CHEBI:27393
ChEBI
1.0
CPD-3743
BioCyc
53477893
PubChem-compound
3.0
CHEBI:28477
ChEBI
559142
ChemSpider
(24R)-Cholest-5-ene-3-β,7-α,24-triol
NAD
C27H46O3
(24R)-Cholest-5-ene-3-β,7-α,24-triol
418.3447
BTO:0000759
BRENDA TISSUE ONTOLOGY
Choloyl-CoA
Taurocholic acid
5742
ChemSpider
C01301
KEGG Compound
CHEBI:16474
ChEBI
C00695
KEGG Compound
1.0
CHEBI:27379
ChEBI
3'-AMP
389556
ChemSpider
C01794
KEGG Compound
3a,7a,12a-Trihydroxy-5b-cholestan-26-al
389554
ChemSpider
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@@H](O)C(=O)NCCC(=O)NCCS
1.0
439164
PubChem-compound
37610
ChemSpider
1.0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C
1.0
BiologicalState464
Rattus norvegicus, Liver
A
3α,7α,12α-Trihydroxy-5β-cholestanoic acid
Adenosine triphosphate
C03990
KEGG Compound
Q4QQV7
UniProt
1.0
1.0
AH2
HMDB0002197
HMDB
2733768
PubChem-compound
CHEBI:28047
ChEBI
C00008
KEGG Compound
C00007
KEGG Compound
C00249
KEGG Compound
C00006
KEGG Compound
CHEBI:18009
ChEBI
C00001
KEGG Compound
NADP
1.0
C00005
KEGG Compound
C00004
KEGG Compound
C00003
KEGG Compound
C00245
KEGG Compound
C00002
KEGG Compound
CHEBI:83036
ChEBI
C13550
KEGG Compound
5284239
PubChem-compound
SubPathwayInteraction108618
SubPathway108618Reaction
SubPathwayReaction
SubPathwayInteraction108619
SubPathwayReaction
SubPathway108619Reaction
388658
ChemSpider
C00010
KEGG Compound
C24H40O3
Lithocholic acid
376.29776
C00013
KEGG Compound
3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA
1.0
SubPathwayInteraction108620
SubPathway108620Reaction
SubPathwayReaction
O09176
UniProt
1.0
56-65-5
CAS
5775
ChemSpider
53-84-9
CAS
1.0
C15519
KEGG Compound
317-66-8
CAS
Alpha-methylacyl-CoA racemase
7 α,26-Dihydroxy-4-cholesten-3-one
NADP
1.0
3862-25-7
CAS
C00037
KEGG Compound
C01367
KEGG Compound
HMDB0000138
HMDB
P51543
UniProt
C15520
KEGG Compound
SMILES
NCCS(O)(=O)=O
SMILES
[O-]P([O-])(=O)OP([O-])([O-])=O
C04644
KEGG Compound
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
CHEBI:9410
ChEBI
3081084
PubChem-compound
3081085
PubChem-compound
HMDB0001231
HMDB
ReactionCatalysis137830
ACTIVATION
ReactionCatalysis137831
ACTIVATION
ReactionCatalysis137832
ACTIVATION
Propionyl-CoA
193196
ChemSpider
ReactionCatalysis137837
ACTIVATION
Lysosomal acid lipase/cholesteryl ester hydrolase
ReactionCatalysis137833
ACTIVATION
CE(22:2(13Z,16Z))
Prostacyclin synthase
ReactionCatalysis137834
ACTIVATION
ReactionCatalysis137835
ACTIVATION
ReactionCatalysis137836
ACTIVATION
HMDB0001487
HMDB
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
1.0
57-10-3
CAS
C10H16N5O13P3
Adenosine triphosphate
506.99576
C27H46O5
3α,7α,12α-Trihydroxy-5β-cholestanoic acid
450.33453
3a,7a-Dihydroxy-5b-cholestanoyl-CoA
HMDB0002103
HMDB
41211
PubChem-compound
HMDB0001496
HMDB
C15557
KEGG Compound
962
PubChem-compound
ReactionCatalysis137810
ACTIVATION
1.0
3α,7α-Dihydroxycoprostanic acid
ReactionCatalysis137815
ACTIVATION
ReactionCatalysis137816
ACTIVATION
110306
ChemSpider
ReactionCatalysis137817
ACTIVATION
ReactionCatalysis137818
ACTIVATION
ReactionCatalysis137811
ACTIVATION
ReactionCatalysis137812
ACTIVATION
ReactionCatalysis137813
ACTIVATION
ReactionCatalysis137814
ACTIVATION
1.0
SMILES
O=O
C03594
KEGG Compound
ReactionCatalysis137808
ACTIVATION
Chenodeoxycholic acid glycine conjugate
SubPathwayInput
ReactionCatalysis137809
ACTIVATION
CHENODEOXYCHOLOYLTAURINE
BioCyc
HMDB0002111
HMDB
SMILES
[H][C@@]12CCC(C(C)CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3OP(O)(O)=O)N3C=NC4=C3N=CN=C4N)C1(C)[C@@H](O)C[C@@]1([H])C2[C@H](O)CC2C[C@H](O)CCC12C
ReactionCatalysis137820
ACTIVATION
ReactionCatalysis137821
ACTIVATION
ReactionCatalysis137826
ACTIVATION
ReactionCatalysis137827
ACTIVATION
ReactionCatalysis137828
ACTIVATION
ReactionCatalysis137829
ACTIVATION
ReactionCatalysis137822
ACTIVATION
ReactionCatalysis137823
ACTIVATION
7a-Hydroxy-cholestene-3-one
ReactionCatalysis137824
ACTIVATION
CHEBI:34310
ChEBI
Deoxycholic acid
SubPathwayOutput
ReactionCatalysis137825
ACTIVATION
Cholic acid
SubPathwayInput
ReactionCatalysis137819
ACTIVATION
CHEBI:76591
ChEBI
C24H40O4
Deoxycholic acid
392.29266
HMDB0001275
HMDB
C24H40O5
Cholic acid
408.28757
1.0
985
PubChem-compound
3a,7a-Dihydroxy-5b-cholestane
644102
PubChem-compound
27-HYDROXYCHOLESTEROL
BioCyc
1.0
1.0
HMDB0006737
HMDB
1.0
123976
PubChem-compound
NADH
BioCyc
53477807
PubChem-compound
977
PubChem-compound
ReactionCatalysis137804
ACTIVATION
123743
PubChem-compound
ReactionCatalysis137805
ACTIVATION
ReactionCatalysis137806
ACTIVATION
ReactionCatalysis137807
ACTIVATION
ReactionCatalysis137800
ACTIVATION
ReactionCatalysis137801
ACTIVATION
ReactionCatalysis137802
ACTIVATION
ReactionCatalysis137803
ACTIVATION
Peroxisomal multifunctional enzyme type 2
17215925
ChemSpider
CHEBI:37998
ChEBI
1.0
CHEBI:2290
ChEBI
C04483
KEGG Compound
1.0
NADH
C27H48O3
5-b-Cholestane-3a ,7a ,12a-triol
420.36035
64907-22-8
CAS
Q64631
UniProt
HMDB0000538
HMDB
1123
PubChem-compound
C05337
KEGG Compound
Cholesterol
SubPathwayOutput
Q64639
UniProt
6816
PubChem-compound
C27H46O
Cholesterol
386.35486
C17333
KEGG Compound
1.0
C27H44O2
7a-Hydroxy-cholestene-3-one
400.33414
5997
PubChem-compound
5-b-Cholestane-3a ,7a ,12a-triol
17974-66-2
CAS
1.0
1.0
C26H43NO5
Chenodeoxycholic acid glycine conjugate
449.31412
1.0
547-98-8
CAS
C26H43NO5
Deoxycholic acid glycine conjugate
449.31412
C27H46O4
3α,7α-Dihydroxycoprostanic acid
434.3396
1.0
SMP0120871
SMPDB
2461-62-3
CAS
167758
ChemSpider
Taurocholic acid
SubPathwayInput
25-Hydroxycholesterol
1.0
1.0
C05122
KEGG Compound
PW122132
PathWhiz
1.0
CHEBI:2288
ChEBI
C27H46O2
25-Hydroxycholesterol
402.3498
C26H45NO7S
Taurocholic acid
515.2917
Lysosomal acid lipase/cholesteryl ester hydrolase
C17335
KEGG Compound
C17336
KEGG Compound
53481010
PubChem-compound
C17337
KEGG Compound
NADPH
BioCyc
1.0
1.0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
CPD-6641
BioCyc
HMDB0001419
HMDB
440985
PubChem-compound
58-68-4
CAS
HMDB0001423
HMDB
SMILES
[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O
C2H5NO2
Glycine
75.03203
CHEBI:15519
ChEBI
SMILES
[H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2
P70540
UniProt
3 α,7 α,24-Trihydroxy-5β-cholestanoyl-CoA
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O
NADPH
Liver
SMILES
[H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
Glycocholic acid
SubPathwayInput
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O
CHEBI:28834
ChEBI
CHEBI:27505
ChEBI
C26H43NO6
Glycocholic acid
465.30905
Q6LDE7
UniProt
3 beta-hydroxysteroid dehydrogenase type 7
516-90-5
CAS
C21H29N7O14P2
NADH
665.12476
Glycine
HMDB0000359
HMDB
5957
PubChem-compound
640-79-9
CAS
CPD-202
BioCyc
1.0
CHEBI:15756
ChEBI
HMDB0000123
HMDB
C27H46O2
7a-Hydroxycholesterol
402.3498
HMDB0001457
HMDB
GO:0005737
GENE ONTOLOGY
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O
7a-Hydroxycholesterol
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O
1.0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
CHEBI:17500
ChEBI
53481407
PubChem-compound
1.0
10116
TAXONOMY
53481409
PubChem-compound
5682
ChemSpider
C27H42O4
7α-Hydroxy-3-oxo-4-cholestenoate
430.30832
343282
ChemSpider
C48H80N7O20P3S
3 α,7 α,24-Trihydroxy-5β-cholestanoyl-CoA
1199.4392
C27H48O3
3 α,7 α,26-Trihydroxy-5β-cholestane
420.36035
1091
ChemSpider
C27H44O3
7 α,26-Dihydroxy-4-cholesten-3-one
416.32904
C27H44O4
3β,7α-Dihydroxy-5-cholestenoate
432.32397
GLYCOCHOLIC_ACID
BioCyc
C27H44O3
3 β-Hydroxy-5-cholestenoate
416.32904
14000-31-8
CAS
CO-A
BioCyc
CHEBI:15339
ChEBI
CPD-8475
BioCyc
5675
ChemSpider
CHEBI:36259
ChEBI
160520
PubChem-compound
Water
862-53-3
CAS
1.0
HMDB0006247
HMDB
Q5M8A2
UniProt
SMILES
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1
10128492
ChemSpider
516-50-7
CAS
1.0
6557
ChemSpider
103116
ChemSpider
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C=O
Transport8030
false
Cholesterol (→) Transport: Rattus norvegicus, Extracellular Space to Rattus norvegicus, Liver, Cell
LEFT_TO_RIGHT
Transport8031
false
CE(22:2(13Z,16Z)) (→) Transport: Rattus norvegicus, Extracellular Space to Rattus norvegicus, Liver, Cell
LEFT_TO_RIGHT
7α-Hydroxy-3-oxo-4-cholestenoate
CHEBI:28865
ChEBI
HMDB0000951
HMDB
3β,7α-Dihydroxy-5-cholestenoate
3 α,7 α,26-Trihydroxy-5β-cholestane
439573
PubChem-compound
CHEBI:15539
ChEBI
3 β-Hydroxy-5-cholestenoate
SMP0000023
SMPDB
P97562
UniProt
GO:0005783
GENE ONTOLOGY
1.0
107-35-7
CAS
53481412
PubChem-compound
1.0
1.0
7782-44-7
CAS
6675
PubChem-compound
HMDB0000722
HMDB
GO:0005777
GENE ONTOLOGY
SMILES
[H][C@@]12CCC([C@H](C)CC[C@@H](O)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C
4444355
ChemSpider
4444354
ChemSpider
1.0
1.0
115538-84-6
CAS
3.0
Non-specific lipid-transfer protein
CHEBI:15377
ChEBI
CHEBI:16466
ChEBI
1.0
HMDB0006281
HMDB
30776546
ChemSpider
CHEBI:15379
ChEBI
CHEBI:18402
ChEBI
HMDB0006280
HMDB
C05464
KEGG Compound
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(O)=O
CHEBI:13193
ChEBI
Cholesterol-esters
BioCyc
Lithocholyltaurine
SubPathwayOutput
CHEBI:81015
ChEBI
HMDB0006292
HMDB
1.0
25-Hydroxycholesterol
HMDB0011644
HMDB
1.0
TAUROLITHOCHOLATE-SULFATE
BioCyc
13628315
ChemSpider
9903
PubChem-compound
HMDB0000518
HMDB
HMDB0000761
HMDB
CHEBI:29746
ChEBI
11966205
PubChem-compound
85-61-0
CAS
434-13-9
CAS
6022
PubChem-compound
937
ChemSpider
CHOLESTEROL
BioCyc
1.0
1.0
2338356
ChemSpider
C26H45NO6S
Taurodeoxycholic acid
499.29675
1.0
C27H48O4
27-Deoxy-5b-cyprinol
436.35526
NAD
CE(22:2(13Z,16Z))
122312
PubChem-compound
ATP
BioCyc
1.0
PW000050
PathWhiz
HMDB0006887
HMDB
360-65-6
CAS
HMDB0006888
HMDB
HMDB0006889
HMDB
Q64194
UniProt
388578
ChemSpider
CHEBI:16113
ChEBI
Lithocholic acid glycine conjugate
SubPathwayOutput
CHEBI:16359
ChEBI
1.0
Reduced acceptor
Reaction147538
false
7a-Hydroxy-5b-cholestan-3-one + NAD → 3a,7a-Dihydroxy-5b-cholestane + NADP
LEFT_TO_RIGHT
109066
ChemSpider
1.3.1.3
false
1.3.1.3
7a-Hydroxy-cholestene-3-one + NADPH ← 7a-Hydroxy-5b-cholestan-3-one + NADP
RIGHT_TO_LEFT
27-Deoxy-5b-cyprinol
CHEBI:15022
ChEBI
952
ChemSpider
474-74-8
CAS
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O
6561-58-6
CAS
SMILES
CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C
SMILES
[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H](O)C2)C(C)CCC(O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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
HMDB0006894
HMDB
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O
SMILES
CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C
HMDB0006895
HMDB
SMILES
C[C@H](CCCC(C)C(O)=O)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
HMDB0006890
HMDB
HMDB0006891
HMDB
HMDB0006892
HMDB
HMDB0006893
HMDB
7-a,27-Dihydroxycholesterol
1.14.13.15
false
1.14.13.15
3a,7a-Dihydroxy-5b-cholestane + 3 NADPH + 3 Oxygen → 3 α,7 α,26-Trihydroxy-5β-cholestane + 3 NADP + 3 Water
LEFT_TO_RIGHT
1.14.13.15
false
1.14.13.15
3 α,7 α,26-Trihydroxy-5β-cholestane → 3a,7a-Dihydroxy-5b-cholestan-26-al
LEFT_TO_RIGHT
1.14.13.15
false
1.14.13.15
3a,7a-Dihydroxy-5b-cholestan-26-al → 3α,7α-Dihydroxycoprostanic acid
LEFT_TO_RIGHT
6.2.1.7
false
6.2.1.7
3α,7α-Dihydroxycoprostanic acid + Adenosine triphosphate + Coenzyme A → 3'-AMP + 3a,7a-Dihydroxy-5b-cholestanoyl-CoA + Pyrophosphate
LEFT_TO_RIGHT
C02528
KEGG Compound
5.1.99.4
false
5.1.99.4
3a,7a-Dihydroxy-5b-cholestanoyl-CoA → 3a,7a-Dihydroxy-5b-cholestanoyl-CoA
LEFT_TO_RIGHT
C00100
KEGG Compound
1.17.99.3
false
1.17.99.3
3a,7a-Dihydroxy-5b-cholestanoyl-CoA + Water → 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA
LEFT_TO_RIGHT
Reaction147546
false
3 α,7 α,24-Trihydroxy-5β-cholestanoyl-CoA → Chenodeoxycholoyl-CoA + Water
LEFT_TO_RIGHT
2.3.1.176
false
2.3.1.176
Chenodeoxycholoyl-CoA + Coenzyme A → Chenodeoxycholoyl-CoA + Propionyl-CoA
LEFT_TO_RIGHT
Reaction147548
false
Chenodeoxycholoyl-CoA + Taurine → Taurochenodesoxycholic acid
LEFT_TO_RIGHT
Cholesterol
Reaction147549
false
Chenodeoxycholoyl-CoA + Glycine → Chenodeoxycholic acid glycine conjugate + Glycocholic acid
LEFT_TO_RIGHT
4.0
1.0
Rattus norvegicus
PPI
BioCyc
81-24-3
CAS
11954197
PubChem-compound
7a-Hydroxy-5b-cholestan-3-one
C24H40N7O17P3S
Propionyl-CoA
823.1414
6.2.1.7
false
6.2.1.7
Adenosine triphosphate + Chenodeoxycholoyl-CoA + Cholic acid → 3'-AMP + Chenodeoxycholic acid + Pyrophosphate
LEFT_TO_RIGHT
Reaction147551
false
7a-Hydroxycholesterol + NAD → 7a-Hydroxy-cholestene-3-one + NADH
LEFT_TO_RIGHT
1.14.13.95
false
1.14.13.95
7a-Hydroxy-cholestene-3-one + NADPH + Oxygen → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Water
LEFT_TO_RIGHT
Water
1.14.13.17
false
1.14.13.17
Cholesterol + NADPH + Oxygen → 7a-Hydroxycholesterol + NADP + Water
LEFT_TO_RIGHT
3.1.1.13
false
3.1.1.13
CE(22:2(13Z,16Z)) + Water → Cholesterol + Palmitic acid
LEFT_TO_RIGHT
1.3.1.3
false
1.3.1.3
7a,12a-Dihydroxy-cholestene-3-one + NADPH → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADP
LEFT_TO_RIGHT
1.14.13.15
false
1.14.13.15
5-b-Cholestane-3a ,7a ,12a-triol + 3 NADPH + 3 Oxygen → 27-Deoxy-5b-cyprinol + 3 NADP + 4 Water
LEFT_TO_RIGHT
Cytosol
Reaction147557
false
7a,12a-Dihydroxy-5b-cholestan-3-one + NADP → 5-b-Cholestane-3a ,7a ,12a-triol + NADPH
LEFT_TO_RIGHT
1.14.13.15
false
1.14.13.15
27-Deoxy-5b-cyprinol + 3 NADPH + 3 Oxygen → 3a,7a,12a-Trihydroxy-5b-cholestan-26-al + 3 NADP + 4 Water
LEFT_TO_RIGHT
388310
ChemSpider
1.14.13.15
false
1.14.13.15
3a,7a,12a-Trihydroxy-5b-cholestan-26-al → 3α,7α,12α-Trihydroxy-5β-cholestanoic acid
LEFT_TO_RIGHT
4675-38-1
CAS
C02530
KEGG Compound
221493
PubChem-compound
C26H45NO6S
Taurochenodesoxycholic acid
499.29675
3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA
53477732
PubChem-compound
6.2.1.7
false
6.2.1.7
3α,7α,12α-Trihydroxy-5β-cholestanoic acid + Adenosine triphosphate + Coenzyme A → 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + Adenosine diphosphate + Pyrophosphate
LEFT_TO_RIGHT
5.1.99.4
false
5.1.99.4
3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA → 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA
LEFT_TO_RIGHT
1.17.99.3
false
1.17.99.3
3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + Acceptor + Water → 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA + Reduced acceptor
LEFT_TO_RIGHT
5-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL
BioCyc
Reaction147563
false
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA + NAD → 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + NADH
LEFT_TO_RIGHT
Reaction147564
false
Choloyl-CoA + Taurine → Coenzyme A + Taurocholic acid
LEFT_TO_RIGHT
Chenodeoxycholoyl-CoA
Reaction147565
false
Choloyl-CoA + Glycine → Coenzyme A + Glycocholic acid
LEFT_TO_RIGHT
C04722
KEGG Compound
6.2.1.7
false
6.2.1.7
3'-AMP + Choloyl-CoA + Pyrophosphate → Adenosine triphosphate + Cholic acid + Coenzyme A
LEFT_TO_RIGHT
7-a,25-Dihydroxycholesterol
1.14.13.98
false
1.14.13.98
Cholesterol + NADPH + Oxygen → 24-Hydroxycholesterol + NADP + Water
LEFT_TO_RIGHT
7-a,27-Dihydroxycholesterol
PROPIONYL-COA
BioCyc
1.14.13.99
false
1.14.13.99
24-Hydroxycholesterol + NADPH + Oxygen → (24R)-Cholest-5-ene-3-β,7-α,24-triol + NADP + Water
LEFT_TO_RIGHT
CHEBI:18361
ChEBI
1.14.13.100
false
1.14.13.100
25-Hydroxycholesterol + NADPH + Oxygen → 7-a,25-Dihydroxycholesterol + NADP + Water
LEFT_TO_RIGHT
CHEBI:17278
ChEBI
Q9ES38
UniProt
Oxygen
57-88-5
CAS
110495
ChemSpider
1.14.13.100
false
1.14.13.100
Cholesterol + 3 NADPH + 3 Oxygen → 27-Hydroxycholesterol + 3 NADP + 4 Water
LEFT_TO_RIGHT
1.14.13.17
false
1.14.13.17
27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Water
LEFT_TO_RIGHT
Taurochenodesoxycholic acid
SubPathwayInput
1.14.13.100
false
1.14.13.100
27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Water
LEFT_TO_RIGHT
1.14.13.15
false
1.14.13.15
27-Hydroxycholesterol + 3 NADPH + 3 Oxygen → 3 β-Hydroxy-5-cholestenoate + 3 NADP + 4 Water
LEFT_TO_RIGHT
C21H28N7O14P2
NAD
664.11694
1.14.13.100
false
1.14.13.100
3 β-Hydroxy-5-cholestenoate + NADPH + Oxygen → 3β,7α-Dihydroxy-5-cholestenoate + NADP + Water
LEFT_TO_RIGHT
Reaction147575
false
3β,7α-Dihydroxy-5-cholestenoate + NAD → 7α-Hydroxy-3-oxo-4-cholestenoate + NADH
LEFT_TO_RIGHT
Reaction147576
false
3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA + Water → 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA
LEFT_TO_RIGHT
2.3.1.176
false
2.3.1.176
3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + Coenzyme A → Choloyl-CoA + Propionyl-CoA
LEFT_TO_RIGHT
5-BETA-CHOLESTANE-3-ALPHA7-TETRAOL
BioCyc
Taurine
1.14.99.38
false
1.14.99.38
AH2 + Cholesterol + Oxygen → 25-Hydroxycholesterol + A + Water
LEFT_TO_RIGHT
Reaction147579
false
7-a,27-Dihydroxycholesterol + NADP → 7 α,26-Dihydroxy-4-cholesten-3-one + NADPH
LEFT_TO_RIGHT
HMDB0000902
HMDB
C49H84O2
CE(22:2(13Z,16Z))
704.64716
Extracellular Space
60731-52-4
CAS
NAD(P)
BioCyc
Reaction147580
false
3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA + Water → 3 α,7 α,24-Trihydroxy-5β-cholestanoyl-CoA
LEFT_TO_RIGHT
192176
ChemSpider
10133
PubChem-compound
CHEBI:17499
ChEBI
1.0
1.0
1.0
1.0
3a,7a-Dihydroxy-5b-cholestane
3a,7a-Dihydroxy-5b-cholestan-26-al
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
Water
Peroxisome
3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA
7a-Hydroxy-5b-cholestan-3-one
22833539
PubChem-compound
5b-Cyprinol sulfate
C26H43NO4
Lithocholic acid glycine conjugate
433.3192
HMDB0000251
HMDB
HMDB0000250
HMDB
HMDB0001341
HMDB
1.0
CPD-266
BioCyc
NADH
7a,12a-Dihydroxy-5b-cholestan-3-one
27-Hydroxycholesterol
SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
C02592
KEGG Compound
1.0
HMDB0003533
HMDB
2338764
ChemSpider
2338765
ChemSpider
1.0
C45H74N7O19P3S
Chenodeoxycholoyl-CoA
1141.3973
ALPHA-N-DIACETYLNEURAMINYL-23-BETA-D-ETC
BioCyc
3.0
C27H46O3
7-a,25-Dihydroxycholesterol
418.3447
7732-18-5
CAS
C27H46O3
7-a,27-Dihydroxycholesterol
418.3447
25-hydroxycholesterol 7-alpha-hydroxylase
3862-26-8
CAS
Bile acid-CoA:amino acid N-acyltransferase
HMDB0000036
HMDB
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C
1.0
516-35-8
CAS
HMDB0003540
HMDB
NAD
23617285
PubChem-compound
56-40-6
CAS
C00187
KEGG Compound
3 beta-hydroxysteroid dehydrogenase type 7
Bile acid-CoA:amino acid N-acyltransferase
HMDB0001377
HMDB
Cholesterol 7-alpha-monooxygenase
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
53477716
PubChem-compound
22833540
PubChem-compound
HMDB0001374
HMDB
1.0
5800
ChemSpider
730
ChemSpider
Cholesterol 25-hydroxylase
387316
PubChem-compound
Lithocholic acid
SubPathwayOutput
1.0
53477903
PubChem-compound
53477905
PubChem-compound
53477904
PubChem-compound
53477906
PubChem-compound
389810
ChemSpider
58-64-0
CAS
3a,7a-Dihydroxy-5b-cholestanoyl-CoA
HMDB0000067
HMDB
24747221
ChemSpider
960
ChemSpider
C48H80N7O19P3S
3a,7a-Dihydroxy-5b-cholestanoyl-CoA
1183.4442
Choloyl-CoA
Bile acyl-CoA synthetase
1.0
C27H46O2
27-Hydroxycholesterol
402.3498
Sterol 26-hydroxylase, mitochondrial
C27H46O3
7a,12a-Dihydroxy-5b-cholestan-3-one
418.3447
2140-46-7
CAS
3-oxo-5-beta-steroid 4-dehydrogenase
22833512
PubChem-compound
C27H48O8S
5b-Cyprinol sulfate
532.307
C48H78N7O20P3S
3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA
1197.4235
C48H80N7O21P3S
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA
1215.4341
83-44-3
CAS
H2O
Water
18.010565
C48H78N7O21P3S
3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA
1213.4185
C27H46O2
7a-Hydroxy-5b-cholestan-3-one
402.3498
C27H48O2
3a,7a-Dihydroxy-5b-cholestane
404.36542
SMILES
NCC(O)=O
1.0
C26H45NO5S
Lithocholyltaurine
483.30185
17215983
ChemSpider
17215984
ChemSpider
547-96-6
CAS
NAD
BioCyc
1.0
C27H46O3
3a,7a-Dihydroxy-5b-cholestan-26-al
418.3447
C48H78N7O19P3S
3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA
1181.4286
Cytochrome P450 3A9
3-alpha-hydroxysteroid dehydrogenase
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C
3-alpha-hydroxysteroid dehydrogenase
Peroxisomal acyl-coenzyme A oxidase 2
Deoxycholic acid glycine conjugate
SubPathwayOutput
C05448
KEGG Compound
3080603
PubChem-compound
C05447
KEGG Compound
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)CO
C05444
KEGG Compound
108790
ChemSpider
Taurodeoxycholic acid
SubPathwayOutput
C05446
KEGG Compound
C05445
KEGG Compound
SMILES
[H][C@]12CCC(C(C)CCCC(C)C)[C@@]1(C)C([H])(O)C[C@@]1([H])C2[C@H](O)CC2CC(=O)CC[C@]12C
C05451
KEGG Compound
SMILES
[H][C@@]12CCC(C(C)CCC(=O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3OP(O)(O)=O)N3C=NC4=C3N=CN=C4N)C1(C)[C@@H](O)C[C@@]1([H])C2[C@H](O)C[C@]2([H])C[C@H](O)CCC12C
SMILES
CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C
C27H44O3
7a,12a-Dihydroxy-cholestene-3-one
416.32904
Acceptor
C05450
KEGG Compound
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
C05453
KEGG Compound
C05452
KEGG Compound
SMILES
CC(CCCC(C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C)C=O
Taurine
SMILES
CC(CCCC(CO)COS(O)(=O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3C[C@@H](O)[C@]12C
1.0
HMDB0000896
HMDB
475-31-0
CAS
SMILES
CC(CC\C=C(/C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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)C1CCC2C3[C@H](O)C[C@]4([H])C[C@H](O)CCC4(C)C3C[C@H](O)C12C
SMILES
O
SMILES
[H][C@@]12C[C@H](O)CCC1(C)C1C[C@H](O)C3(C)C(CCC3C1[C@H](O)C2)C(C)CCC(O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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
SMILES
C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C
1.0
Alpha-methylacyl-CoA racemase
C24H40O4
Chenodeoxycholic acid
392.29266
Pyrophosphate
1.0
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA
9519
ChemSpider
1.0
CHEBI:37623
ChEBI
C05455
KEGG Compound
SMILES
CC(CC\C=C(/C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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)C1CCC2C3[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)C3CC[C@]12C
C05454
KEGG Compound
C05457
KEGG Compound
HMDB0001993
HMDB
1.0
C05463
KEGG Compound
C05460
KEGG Compound
CHEBI:37616
ChEBI
CHEBI:15846
ChEBI
Peroxisomal multifunctional enzyme type 2
1.0
ADP
BioCyc
Non-specific lipid-transfer protein
ReactionCatalysis137796
ACTIVATION
Chenodeoxycholoyl-CoA
ReactionCatalysis137797
ACTIVATION
ReactionCatalysis137798
ACTIVATION
ReactionCatalysis137799
ACTIVATION
53-59-8
CAS
ReactionCatalysis137795
ACTIVATION
C05466
KEGG Compound
C05465
KEGG Compound
C05468
KEGG Compound
C05467
KEGG Compound
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O
GO:0005829
GENE ONTOLOGY
Chenodeoxycholic acid
SubPathwayInput
7a,12a-Dihydroxy-cholestene-3-one
Bile acid-CoA:amino acid N-acyltransferase
3 beta-hydroxysteroid dehydrogenase type 7
CHEBI:16908
ChEBI
Q63688
UniProt
NADPH
3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA
Palmitic acid
NADP
Cholesterol 7-alpha-monooxygenase
C21H30N7O17P3
NADPH
745.0911
C16H32O2
Palmitic acid
256.24023
25-hydroxycholesterol 7-alpha-hydroxylase
C21H29N7O17P3
NADP
744.08325
474-25-9
CAS
10128154
ChemSpider
GLY
BioCyc
141053
ChemSpider
Peroxisomal acyl-coenzyme A oxidase 2
1.0
Q642G0
UniProt
C06341
KEGG Compound
1.0
Choloyl-CoA
C06340
KEGG Compound
HMDB0000698
HMDB
HMDB0000217
HMDB
Prostacyclin synthase
Oxygen
1.0
CHEBI:15891
ChEBI
SMILES
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
HMDB0000221
HMDB
5280796
PubChem-compound
5257127
PubChem-compound
5280797
PubChem-compound
SMILES
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
SMILES
CCCCCCCCCCCCCCCC(O)=O
CHEBI:2149
ChEBI
121948
PubChem-compound
HMDB0000220
HMDB
53-57-6
CAS
HMDB0012453
HMDB
HMDB0012454
HMDB
HMDB0012455
HMDB
4447327
ChemSpider
HMDB0012456
HMDB
Cytochrome P450 3A9
HMDB0012458
HMDB
HMDB0012459
HMDB
C2H7NO3S
Taurine
125.01466
O7P2
Pyrophosphate
173.91193
1.0
CHEBI:28701
ChEBI
27-Hydroxylase Deficiency
Bile acyl-CoA synthetase
SMILES
[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H](O)C2)C(C)CCCC(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
Steroid Biosynthesis
SubPathway
Adenosine diphosphate
CHEBI:28931
ChEBI
C10H15N5O10P2
Adenosine diphosphate
427.02942
GO:0005615
GENE ONTOLOGY
3-alpha-hydroxysteroid dehydrogenase
1.0
Coenzyme A
3-oxo-5-beta-steroid 4-dehydrogenase
1.0
Sterol 26-hydroxylase, mitochondrial
C01921
KEGG Compound
1.0
3.0
Endoplasmic Reticulum
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
1.0
15313-69-6
CAS
Q62969
UniProt
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C
CHEBI:1146900
ChEBI
440420
PubChem-compound
A
AH2
Coenzyme A
C21H36N7O16P3S
Coenzyme A
767.11523
24-Hydroxycholesterol
CHEBI:27428
ChEBI
Cytoplasm
84-21-9
CAS
21252277
PubChem-compound
C27H46O2
24-Hydroxycholesterol
402.3498
CHEBI:15422
ChEBI
Intestinal Microflora
SubPathway
CHEBI:16755
ChEBI
115538-85-7
CAS
388299
ChemSpider
Acceptor
Reduced acceptor
O2
Oxygen
31.98983
193321
PubChem-compound
1.0
C45H74N7O20P3S
Choloyl-CoA
1157.3922
CHEBI:16525
ChEBI
6423
ChemSpider
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO
Intestinal Microflora
SubPathway
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O
CHEBI:16761
ChEBI
440677
PubChem-compound
440675
PubChem-compound
CHEBI:27403
ChEBI
HMDB0000601
HMDB
CHEBI:15428
ChEBI
Coenzyme A
P31210
UniProt
CHEBI:16577
ChEBI
9728
ChemSpider
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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
389367
ChemSpider
5893
PubChem-compound
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CO
115245
PubChem-compound
439479
PubChem-compound
1.0
1.0
CHEBI:27471
ChEBI
5886
PubChem-compound
CHEBI:15494
ChEBI
HMDB0000619
HMDB
2015539
ChemSpider
1.0
440690
PubChem-compound
81-25-4
CAS
Reaction1564
false
27-Deoxy-5b-cyprinol → 5b-Cyprinol sulfate
LEFT_TO_RIGHT
CPD-7239
BioCyc
HMDB0000626
HMDB
Cholesterol
1.0
222528
PubChem-compound
SMILES
CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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
4725-24-0
CAS
HMDB0000631
HMDB
CHEBI:27458
ChEBI
CHEBI:28540
ChEBI
CHEBI:16325
ChEBI
CHEBI:17899
ChEBI
3836-01-9
CAS
HMDB0000637
HMDB
CPD-7243
BioCyc
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O
CPD-7241
BioCyc
O35048
UniProt