3-Hydroxy-3-methylglutaryl-coenzyme A reductase
1.0
388357
ChemSpider
6022
PubChem-compound
Farnesyl pyrophosphate
1.0
C23H38N7O17P3S
Acetyl-CoA
809.1258
P04035
UniProt
937
ChemSpider
MEVALONATE
BioCyc
Squalene monooxygenase
388353
ChemSpider
3-Hydroxy-3-methylglutaryl-coenzyme A reductase
HMDB0001188
HMDB
C00448
KEGG Compound
1.0
111-02-4
CAS
NADPH
ATP
BioCyc
Acetoacetyl-CoA
559142
ChemSpider
C30H50O
(S)-2,3-Epoxysqualene
426.38617
SMP0121055
SMPDB
1.0
5742
ChemSpider
Acetyl-CoA
SubPathwayOutput
1.0
C00332
KEGG Compound
Hydrogen Ion
CHEBI:16474
ChEBI
952
ChemSpider
EPOXYSQUALENE
BioCyc
(S)-2,3-Epoxysqualene
C00341
KEGG Compound
CHEBI:17211
ChEBI
445713
PubChem-compound
1010
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
PPI
BioCyc
1.0
5666-16-0
CAS
1.0
1.0
Cytosol
1.0
C00356
KEGG Compound
C00235
KEGG Compound
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C
Mevalonate Pathway
CHEBI:16057
ChEBI
C10H20O7P2
Geranyl-PP
314.06842
22833574
PubChem-compound
C00009
KEGG Compound
C00008
KEGG Compound
C00129
KEGG Compound
1158
ChemSpider
C00007
KEGG Compound
C00006
KEGG Compound
CHEBI:18009
ChEBI
C5H12O7P2
Dimethylallylpyrophosphate
246.00583
C00001
KEGG Compound
NADP
CHEBI:18361
ChEBI
C00005
KEGG Compound
CHEBI:18367
ChEBI
1032
ChemSpider
Acetyl-CoA acetyltransferase, mitochondrial
C00002
KEGG Compound
559060
ChemSpider
150-97-0
CAS
P37268
UniProt
Geranyl-PP
Diphosphomevalonate decarboxylase
C01107
KEGG Compound
C30H50O
Lanosterol
426.38617
1.0
763-10-0
CAS
2.7.1.36
false
2.7.1.36
Adenosine triphosphate + Mevalonic acid → Adenosine diphosphate + Hydrogen Ion + Mevalonic acid-5P
LEFT_TO_RIGHT
Adenosine triphosphate
1.1.1.34
false
1.1.1.34
Coenzyme A + Mevalonic acid + 2 NADP ← 3-Hydroxy-3-methylglutaryl-CoA + 2 Hydrogen Ion + 2 NADPH
RIGHT_TO_LEFT
C00011
KEGG Compound
C00010
KEGG Compound
2.3.3.10
false
2.3.3.10
Acetoacetyl-CoA + Acetyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoA + Coenzyme A + Hydrogen Ion
LEFT_TO_RIGHT
Reaction179282
false
2 Acetyl-CoA ↔ Acetoacetyl-CoA + Coenzyme A
REVERSIBLE
Reaction179289
false
Geranyl-PP + Isopentenyl pyrophosphate → Farnesyl pyrophosphate + Pyrophosphate
LEFT_TO_RIGHT
2.5.1.10
false
2.5.1.10
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Geranyl-PP + Pyrophosphate
LEFT_TO_RIGHT
Squalene monooxygenase
4.1.1.33
false
4.1.1.33
(R)-Mevalonic acid-5-pyrophosphate + Adenosine triphosphate → Adenosine diphosphate + Carbon dioxide + Isopentenyl pyrophosphate + Phosphate
LEFT_TO_RIGHT
C00013
KEGG Compound
NAD(P)
BioCyc
Reaction179291
false
FMNH2 + Oxygen + Squalene → (S)-2,3-Epoxysqualene + Flavin Mononucleotide + Hydrogen Ion + Water
LEFT_TO_RIGHT
3-HYDROXY-3-METHYL-GLUTARYL-COA
BioCyc
Reaction179290
false
2 Farnesyl pyrophosphate + Hydrogen Ion + NADPH → NADP + 2 Pyrophosphate + Squalene
LEFT_TO_RIGHT
Pyrophosphate
CHEBI:16048
ChEBI
H
Hydrogen Ion
1.007825
Coenzyme A
445995
PubChem-compound
56-65-5
CAS
C00024
KEGG Compound
Squalene synthase
Squalene synthase
CPD-499
BioCyc
647
PubChem-compound
388517
ChemSpider
P53602
UniProt
372-97-4
CAS
3-Hydroxy-3-methylglutaryl-CoA
HMDB0001343
HMDB
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
SMILES
CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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
Peroxisome
HMDB0000256
HMDB
Lanosterol synthase
1.0
Mevalonic acid-5P
HMDB0001347
HMDB
HMDB0000250
HMDB
SMILES
OP(O)(=O)OP(O)(O)=O
HMDB0001341
HMDB
GERANYL-PP
BioCyc
Squalene
Farnesyl pyrophosphate synthase
Acetyl-CoA acetyltransferase, mitochondrial
Hydroxymethylglutaryl-CoA synthase, cytoplasmic
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
10148626
ChemSpider
SMILES
C[C@@](O)(CCOP(O)(O)=O)CC(O)=O
Mevalonic acid
C15H28O7P2
Farnesyl pyrophosphate
382.13104
53477723
PubChem-compound
7732-18-5
CAS
1.0
436
ChemSpider
Water
9029-62-3
CAS
SMILES
CC(O)(CCO)CC(O)=O
C00061
KEGG Compound
C17H23N4O9P
FMNH2
458.12027
Adenosine diphosphate
HMDB0001120
HMDB
HMDB0001484
HMDB
CPD-4211
BioCyc
146-17-8
CAS
C10H16N5O13P3
Adenosine triphosphate
506.99576
FARNESYL-PP
BioCyc
Pyrophosphate
HMDB0001377
HMDB
2.0
HMDB0001251
HMDB
HMDB0001375
HMDB
962
PubChem-compound
5800
ChemSpider
1.0
3-Hydroxy-3-methylglutaryl-CoA
CO2
Carbon dioxide
43.98983
1.0
1.0
C00080
KEGG Compound
SMILES
O=O
2.0
1.0
1.0
HMDB0002111
HMDB
SMILES
C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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
HMDB0001142
HMDB
14265-44-2
CAS
Isopentenyl-diphosphate Delta-isomerase 1
Squalene
58-64-0
CAS
P14324
UniProt
C6H14O10P2
(R)-Mevalonic acid-5-pyrophosphate
308.00623
C01054
KEGG Compound
Farnesyl pyrophosphate synthase
Mevalonate kinase
1.0
SubPathwayInteraction109643
SubPathway109643Reaction
SubPathwayReaction
1.0
644102
PubChem-compound
444493
PubChem-compound
Mevalonic acid
SMILES
CC(=C)CCOP(O)(=O)OP(O)(O)=O
FMNH2
2.0
PW122323
PathWhiz
22833512
PubChem-compound
ACETYL-COA
BioCyc
H2O
Water
18.010565
1.0
393046
ChemSpider
HMDB0001285
HMDB
Lanosterol
Isopentenyl-diphosphate Delta-isomerase 1
977
PubChem-compound
HMDB0059597
HMDB
1.0
2.0
627
ChemSpider
1.0
Q13907
UniProt
P48449
UniProt
1.0
2.0
Isopentenyl pyrophosphate
SMILES
CC1=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=N2
17215925
ChemSpider
HMDB0001981
HMDB
SMILES
O
C6H12O4
Mevalonic acid
148.07356
(R)-Mevalonic acid-5-pyrophosphate
1.0
SQUALENE
BioCyc
HMDB0000538
HMDB
Phosphomevalonate kinase
Lanosterol synthase
Diphosphomevalonate decarboxylase
393270
ChemSpider
6816
PubChem-compound
Water
Glycolysis
SubPathway
ADP
BioCyc
ReactionCatalysis258
ACTIVATION
Dimethylallylpyrophosphate
1553-55-5
CAS
53-59-8
CAS
358-72-5
CAS
1.0
1038
PubChem-compound
79-63-0
CAS
1.0
HMDB0001520
HMDB
GO:0005829
GENE ONTOLOGY
FMN
BioCyc
274
ChemSpider
445395
PubChem-compound
H3O4P
Phosphate
97.9769
3-Hydroxy-3-methylglutaryl-coenzyme A reductase
Phosphomevalonate kinase
C21H30N7O17P3
NADPH
745.0911
Hydrogen Ion
Mitochondrion
C21H28N7O17P3
NADP
743.07544
Acetyl-CoA
NADPH
BioCyc
1.0
449
PubChem-compound
Carbon dioxide
C5H12O7P2
Isopentenyl pyrophosphate
246.00583
CPD-6641
BioCyc
Mevalonic acid-5P
SMP0000040
SMPDB
HMDB0001423
HMDB
SMILES
OP(O)(O)=O
HMDB0000217
HMDB
124-38-9
CAS
2.0
Oxygen
HMDB0001429
HMDB
NADPH
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](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
HMDB0000221
HMDB
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=C2N=CN=C3N)[C@@H](O)[C@H]1O
P24752
UniProt
HMDB0000227
HMDB
C17H21N4O9P
Flavin Mononucleotide
456.1046
393471
ChemSpider
53-57-6
CAS
2.7.4.2
false
2.7.4.2
Adenosine triphosphate + Mevalonic acid-5P → (R)-Mevalonic acid-5-pyrophosphate + Adenosine diphosphate
LEFT_TO_RIGHT
SMILES
O=C=O
H4O7P2
Pyrophosphate
177.94322
C25H40N7O18P3S
Acetoacetyl-CoA
851.13635
1.0
1.0
Acetoacetyl-CoA
1.0
HMDB0001206
HMDB
5957
PubChem-compound
C30H50
Squalene
410.39127
Q15126
UniProt
SMILES
C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O
439400
PubChem-compound
GO:0005739
GENE ONTOLOGY
Adenosine triphosphate
Farnesyl pyrophosphate
C10H15N5O10P2
Adenosine diphosphate
427.02942
GO:0005737
GENE ONTOLOGY
C6H13O7P
Mevalonic acid-5P
228.03989
Coenzyme A
5.4.99.7
false
5.4.99.7
(S)-2,3-Epoxysqualene → Lanosterol
LEFT_TO_RIGHT
CHEBI:17621
ChEBI
Endoplasmic Reticulum
Endoplasmic Reticulum Membrane
CPD-8587
BioCyc
CHEBI:15441
ChEBI
2.0
CHEBI:15440
ChEBI
SMILES
[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
CHEBI:1146900
ChEBI
14000-31-8
CAS
ReactionCatalysis543
ACTIVATION
CO-A
BioCyc
1.0
LANOSTEROL
BioCyc
5675
ChemSpider
72-89-9
CAS
216175
ChemSpider
C21H36N7O16P3S
Coenzyme A
767.11523
Adenosine diphosphate
Cytoplasm
1492-08-6
CAS
1.0
Q14534
UniProt
ACETOACETYL-COA
BioCyc
CHEBI:15422
ChEBI
Coenzyme A
643976
PubChem-compound
6557
ChemSpider
Homo sapiens
SMILES
CC(=O)SCCNC(=O)CCNC(=O)[C@H](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
1.0
1.0
C27H44N7O20P3S
3-Hydroxy-3-methylglutaryl-CoA
911.1575
Hydrogen Ion
CHEBI:25351
ChEBI
O2
Oxygen
31.98983
439214
PubChem-compound
Q01581
UniProt
GO:0005789
GENE ONTOLOGY
Isopentenyl pyrophosphate
GO:0005783
GENE ONTOLOGY
Isopentenyl pyrophosphate
439218
PubChem-compound
CHEBI:16521
ChEBI
1.0
Hydroxymethylglutaryl-CoA synthase, cytoplasmic
CHEBI:16526
ChEBI
Farnesyl pyrophosphate synthase
1.0
73566-35-5
CAS
CHEBI:16761
ChEBI
7782-44-7
CAS
1.0
HMDB0000961
HMDB
246983
PubChem-compound
GO:0005777
GENE ONTOLOGY
Dimethylallylpyrophosphate
Mevalonate kinase
9606
TAXONOMY
C01724
KEGG Compound
358-71-4
CAS
392413
ChemSpider
C01847
KEGG Compound
PW000146
PathWhiz
1.0
Q03426
UniProt
C00751
KEGG Compound
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O
SMILES
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1
1420-36-6
CAS
CHEBI:15377
ChEBI
CHEBI:17436
ChEBI
CHEBI:15379
ChEBI
CHEBI:15378
ChEBI
SMILES
[H+]
4.0
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
5886
PubChem-compound
1.0
CHEBI:16584
ChEBI
Phosphate
ReactionCatalysis169196
ACTIVATION
ReactionCatalysis169195
ACTIVATION
ReactionCatalysis169194
ACTIVATION
ReactionCatalysis169193
ACTIVATION
ReactionCatalysis169191
ACTIVATION
280
PubChem-compound
Acetyl-CoA acetyltransferase, mitochondrial
ReactionCatalysis169190
ACTIVATION
CHEBI:15467
ChEBI
30776536
ChemSpider
CHEBI:15345
ChEBI
1195
PubChem-compound
CHEBI:17407
ChEBI
C00418
KEGG Compound
ReactionCatalysis250
ACTIVATION
ReactionCatalysis169189
ACTIVATION
ReactionCatalysis169188
ACTIVATION
ReactionCatalysis169187
ACTIVATION
FMNH2
BioCyc
17216150
ChemSpider
SMILES
CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O
1.0
5.3.3.2
false
5.3.3.2
Isopentenyl pyrophosphate ↔ Dimethylallylpyrophosphate
REVERSIBLE
NADP
1061
PubChem-compound
Flavin Mononucleotide
1.0
HMDB0001967
HMDB
SMILES
CC(C)=CCO[P@](O)(=O)OP(O)(O)=O
CHEBI:15351
ChEBI
2.0
85-61-0
CAS
11975273
PubChem-compound