Cholesterol biosynthesis

Song BL, Javitt NB, DeBose-Boyd RA. Insig-mediated degradation of HMG CoA reductase stimulated by lanosterol, an intermediate in the synthesis of cholesterol. Cell Metab. 2005 Mar;1(3):179–89. doi: 10.1016/j.cmet.2005.01.001. PMID: 16054061.; Herman GE. Disorders of cholesterol biosynthesis: prototypic metabolic malformation syndromes. Hum Mol Genet. 2003 Apr 01;12 Spec No 1():R75–88. doi: 10.1093/hmg/ddg072. PMID: 12668600.; Gaylor JL. Membrane-Bound Enzymes of Cholesterol Synthesis from Lanosterol. Biochemical and Biophysical Research Communications. 2002 Apr;292(5):1139–46. doi: 10.1006/bbrc.2001.2008.; Russell DW. Cholesterol biosynthesis and metabolism. Cardiovasc Drugs Ther. 1992 Apr;6(2):103–10. doi: 10.1007/bf00054556. PMID: 1390320.; Rudney H, Sexton RC. Regulation of cholesterol biosynthesis. Annu Rev Nutr. 1986;6():245–72. doi: 10.1146/annurev.nu.06.070186.001333. PMID: 3524618.

Metabolites

(S)-2,3-Epoxysqualene

Formula: C30H50O (426.386145)

CAS ID: 54910-48-4

24,25-Dihydrolanosterol

Formula: C30H52O (428.4017942)

CAS ID: 79-62-9

7-Dehydrocholesterol

Formula: C27H44O (384.3391974)

CAS ID: 434-16-2

7-Dehydrodesmosterol

Formula: C27H42O (382.3235482)

CAS ID: 1715-86-2

Cholesterol

Formula: C27H46O (386.3548466)

CAS ID: 57-88-5

CO2

Formula: CO2 (43.98983)

CAS ID: 124-38-9

Desmosterol

Formula: C27H44O (384.3391974)

CAS ID: 313-04-2

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Lanosterol

Formula: C30H50O (426.386145)

CAS ID: 79-63-0

Lathosterol

Formula: C27H46O (386.3548466)

CAS ID: 80-99-9

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

NADP+

Formula: C21H29N7O17P3 (744.0832754)

CAS ID: 53-59-8

NADPH

Formula: C21H30N7O17P3 (745.0911)

CAS ID: 2646-71-1

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Squalene

Formula: C30H50 (410.39123)

CAS ID: 111-02-4

Zymosterol

Formula: C27H44O (384.3391974)

CAS ID: 128-33-6

Zymosterone

Formula: C27H42O (382.3235482)

CAS ID: 27192-37-6

formate

Formula: CHO2 (44.997654600000004)

CAS ID: 71-47-6

(R)-mevalonate

Formula: C6H11O4 (147.0657306)

CAS ID: 1192-42-3

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

ATP(4-)

Formula: C10H12N5O13P3 (502.9644492)

CAS ID:

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9

ADP(3-)

Formula: C10H12N5O10P2 (424.0059412)

CAS ID:

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
2.5.1.-
1.1.1.170 3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating) 3beta-hydroxysteroid-4alpha-carboxylate:NAD(P)+ 3-oxidoreductase (decarboxylating)
1.1.1.210 3beta(or 20alpha)-hydroxysteroid dehydrogenase 3beta(or 20alpha)-hydroxysteroid:NADP+ oxidoreductase
1.1.1.270 3beta-hydroxysteroid 3-dehydrogenase 3beta-hydroxysteroid:NADP+ 3-oxidoreductase
1.1.1.34 hydroxymethylglutaryl-CoA reductase (NADPH) (R)-mevalonate:NADP+ oxidoreductase (CoA-acylating)
1.1.1.62 17beta-estradiol 17-dehydrogenase 17beta-estradiol:NAD(P)+ 17-oxidoreductase
1.14.14.154 sterol 14alpha-demethylase sterol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (14-methyl cleaving)
1.14.14.17 squalene monooxygenase squalene,NADPH-hemoprotein:oxygen oxidoreductase (2,3-epoxidizing
1.14.18.9 4alpha-methylsterol monooxygenase 4,4-dimethyl-5alpha-cholest-7-en-3beta-ol,ferrocytochrome-b5:oxygen oxidoreductase (C4alpha-methyl-hydroxylating)
1.14.19.20 DELTA7-sterol 5(6)-desaturase DELTA7-sterol,ferrocytochrome b5:oxygen oxidoreductase 5,6-dehydrogenating
1.3.1.21 7-dehydrocholesterol reductase cholesterol:NADP+ DELTA7-oxidoreductase
1.3.1.70 DELTA14-sterol reductase 4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol:NADP+ DELTA14-oxidoreductase
1.3.1.72 DELTA24-sterol reductase sterol:NADP+ DELTA24-oxidoreductase
2.3.1.9 acetyl-CoA C-acetyltransferase acetyl-CoA:acetyl-CoA C-acetyltransferase
2.3.3.10 hydroxymethylglutaryl-CoA synthase acetyl-CoA:acetoacetyl-CoA C-acetyltransferase (thioester-hydrolysing, carboxymethyl-forming)
2.5.1.1 dimethylallyltranstransferase prenyl-diphosphate:3-methylbut-3-en-1-yl-diphosphate prenyltranstransferase
2.5.1.10 (2E,6E)-farnesyl diphosphate synthase geranyl-diphosphate:isopentenyl-diphosphate geranyltranstransferase
2.5.1.21 squalene synthase (2E,6E)-farnesyl-diphosphate:(2E,6E)-farnesyl-diphosphate farnesyltransferase
2.5.1.29 geranylgeranyl diphosphate synthase (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase
2.7.1.36 mevalonate kinase ATP:(R)-mevalonate 5-phosphotransferase
2.7.4.2 phosphomevalonate kinase ATP:(R)-5-phosphomevalonate phosphotransferase
3.3.2.11 cholesterol-5,6-oxide hydrolase 5,6alpha-epoxy-5alpha-cholestan-3beta-ol hydrolase
3.6.1.68 geranyl diphosphate phosphohydrolase geranyl-diphosphate phosphohydrolase
4.1.1.33 diphosphomevalonate decarboxylase ATP:(R)-5-diphosphomevalonate carboxy-lyase (adding ATP; isopentenyl-diphosphate-forming)
5.3.3.5 cholestenol DELTA-isomerase DELTA7-Cholestenol DELTA7-DELTA8-isomerase
5.4.99.7 Lanosterol synthase (S)-2,3-Epoxysqualene mutase (cyclizing, lanosterol-forming)


Proteins

Protein ID name full name