7α-Hydroxycholesterol

Multi tool use
7α-Hydroxycholesterol

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Names
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IUPAC name
(3S,7S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
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Identifiers
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CAS Number
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3D model (JSmol)
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- Interactive image
- Interactive image
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ChemSpider
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96891 Y
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IUPHAR/BPS
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MeSH
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7+alpha-hydroxycholesterol
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InChI
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1 Y
Key: OYXZMSRRJOYLLO-RVOWOUOISA-N Y
InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
Key: OYXZMSRRJOYLLO-RVOWOUOIBF
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SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C
O[C@@H]4C/C3=C/[C@@H](O)[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)[C@@]3(C)CC4
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Properties
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Chemical formula
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C27H46O2
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Molar mass
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402.653 g/mol
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Y verify (what is Y N ?)
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Infobox references
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7α-Hydroxycholesterol is a precursor of bile acids, created by cholesterol 7α-hydroxylase. It is the rate-determining step.
References
Cholesterol and steroid metabolic intermediates
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Mevalonate pathway |
to HMG-CoA
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- Acetyl-CoA
- Acetoacetyl-CoA
- HMB
- HMB-CoA
- HMG-CoA
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Ketone bodies |
- Acetone
- Acetoacetic acid
- β-Hydroxybutyric acid
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to DMAPP
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- Mevalonic acid
- Phosphomevalonic acid
- 5-Diphosphomevalonic acid
- Isopentenyl pyrophosphate
- Dimethylallyl pyrophosphate
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Geranyl- |
- Geranyl pyrophosphate
- Geranylgeranyl pyrophosphate
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Carotenoid |
- Prephytoene diphosphate
- Phytoene
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Non-mevalonate pathway |
- DOXP
- MEP
- CDP-ME
- CDP-MEP
- MEcPP
- HMB-PP
- IPP
- DMAPP
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To Cholesterol
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- Farnesyl pyrophosphate
- Squalene
- 2,3-Oxidosqualene
- Lanosterol
- Lanosterol
- Lathosterol
- 7-Dehydrocholesterol
- Cholesterol
- Lanosterol
- Zymosterol
- 7-Dehydrodesmosterol
- Desmosterol
- Cholesterol
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From Cholesterol (to steroids) |
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
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Steroid hormones |
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Nonhuman |
Phytosterols |
- Stigmasterol
- Brassicasterol
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Ergosterols |
- Ergosterol
- Ergocalciferol
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Endogenous steroids
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Precursors |
- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 11β-Hydroxypregnenolone
- 17α-Hydroxypregnenolone
- 21-Hydroxypregnenolone
- 17α,21-Dihydroxypregnenolone
- 11β,17α,21-Trihydroxypregnenolone
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Corticosteroids |
Glucocorticoids |
- 3α,5α-Tetrahydrocorticosterone
- 5α-Dihydrocorticosterone
- 11-Deoxycorticosterone
- 11-Deoxycortisol
- 11-Ketoprogesterone
- 21-Deoxycortisol
- 21-Deoxycortisone
- Corticosterone
- Cortisol
- Cortisone
- 17α-Hydroxypregnenolone
- 17α-Hydroxyprogesterone
- Pregnenolone
- Progesterone
Metabolites: 5α-Dihydrocortisol
- 3α,5α-Tetrahydrocortisol
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Mineralocorticoids |
- 5α-Dihydroaldosterone
- 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
- 11-Deoxycortisol
- 11-Deoxycorticosterone
- 11β-Hydroxyprogesterone (21-deoxycorticosterone)
- 18-Hydroxy-11-deoxycorticosterone
- 18-Hydroxycorticosterone
- 18-Hydroxyprogesterone
- Aldosterone
- Corticosterone
- Cortisol
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Sex steroids |
Androgens |
- 11-Ketodihydrotestosterone
- 11-Ketotestosterone
- 7β-Hydroxyepiandrosterone
- 11β-Hydroxyandrostenedione
- Adrenosterone (11-ketoandrostenedione)
- Androstenediol
- Androstenedione
- Androsterone
- Dehydroandrosterone
- DHEA
- DHEA sulfate
- Dihydrotestosterone
- Epiandrosterone
- Epitestosterone
- 16α-Hydroxyandrostenedione
- 16α-Hydroxy-DHEA
- 16α-Hydroxy-DHEA sulfate
- Testosterone
Metabolites: 3α-Androstanediol
- 3α-Androstanediol glucuronide
- 3β-Androstanediol
- 5β-Dihydrotestosterone
- 3α-Etiocholanediol
- 3β-Etiocholanediol
- Androstanetriols
- Androstenediol sulfate
- Androsterone glucuronide
- Androsterone sulfate
- Dihydrotestosterone glucuronide
- Dihydrotestosterone sulfate
- Etiocholanedione
- Etiocholanolone
- Etiocholanolone glucuronide
- Epietiocholanolone
- Testosterone glucuronide
- Testosterone sulfate
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Estrogens |
Estranes: Estetrol
- Estradiol
- Estrone
- Estriol
- 17α-Estradiol
- 16β-Epiestriol (16β-hydroxyestradiol)
- 17α-Epiestriol (16α-hydroxy-17α-estradiol)
- 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
- 2-Hydroxyestradiol
- 2-Hydroxyestriol
- 2-Hydroxyestrone
- 4-Hydroxyestradiol
- 4-Hydroxyestriol
- 4-Hydroxyestrone
- 4-Methoxyestradiol
- 16α-Hydroxyestrone
Others: 27-Hydroxycholesterol
- 3α-Androstanediol
- 3β-Androstanediol
- 4-Androstenedione
- 5-Androstenediol
- DHEA
- DHEA sulfate
- 7-Keto-DHEA
- 7α-Hydroxy-DHEA
- 16α-Hydroxy-DHEA
Metabolites: 2-Methoxyestradiol
- 2-Methoxyestrone
- 4-Methoxyestrone
- Estradiol glucuronide
- Estradiol 3-glucuronide
- Estradiol sulfate
- Estradiol 17β-sulfate
- Estrone glucuronide
- Estrone sulfate
- Estriol glucuronide
- Estriol sulfate
Lipoidal estradiol (e.g., estradiol stearate, estradiol palmitate)
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Progestogens |
- Progesterone
- 16α-Hydroxyprogesterone
- 17α-Hydroxyprogesterone
- 20α-Dihydroprogesterone
- 20β-Dihydroprogesterone
- 5α-Dihydroprogesterone
- 11-Deoxycorticosterone
- 5α-DHDOC
Metabolites: Allopregnanediol
- Pregnanediol
- Pregnanediol glucuronide
- Pregnanetriol
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Neurosteroids |
Cholestanes: 24S-Hydroxycholesterol
- Cholesterol
Pregnanes: 3α-Dihydroprogesterone
- 3β-Dihydroprogesterone
- 5α-Dihydrocorticosterone
- 5α-Dihydroprogesterone
- 5β-Dihydroprogesterone
- Allopregnanolone
- Corticosterone
- DHC
- DHDOC
- 11-Deoxycorticosterone
- Epipregnanolone
- Isopregnanolone
- Pregnanolone
- Pregnenolone
- Pregnenolone sulfate
- Progesterone
- THB
- THDOC
Androstanes: 3α-Androstanediol
- 3α-Androstenol
- 7-Keto-DHEA
- 7α-Hydroxy-DHEA
- 7β-Hydroxy-DHEA
- 7α-Hydroxyepiandrosterone
- 7β-Hydroxyepiandrosterone
- Androsterone
- DHEA
- DHEA sulfate
- Etiocholanolone
Pheromones: 3α-Androstenol
- 3β-Androstenol
- Androstadienol
- Androstadienone
- Androstenone
- Androsterone
- Estratetraenol
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Others |
Vitamin D: 7-Dehydrocholesterol
- Calcidiol/Calcifediol
- Calcitriol
- Cholecalciferol
Others: 7α-Hydroxycholesterol
- 11α-Hydroxyprogesterone
- 11β-Hydroxyprogesterone
- Cholesterol sulfate
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