Cholesterol sulfate

Names
IUPAC name

[(3S,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]phenanthren-3-yl] hydrogen sulfate

Other names

Cholest-5-en-3β-ol sulfate

Identifiers

CAS Number

* 1256-86-6

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:41321

ChEMBL |

* ChEMBL1231592

ChemSpider |

* 58586

PubChem CID

* 65076

UNII |

* KU576NT9O9

InChI

* InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

Key: BHYOQNUELFTYRT-DPAQBDIFSA-N

* InChI=1/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

Key: BHYOQNUELFTYRT-DPAQBDIFBL

SMILES

* C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C)C

Properties

Chemical formula

| C27H46O4S
Molar mass | 466.72 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Cholesterol sulfate, or cholest-5-en-3β-ol sulfate, is an endogenous steroid and the C3β sulfate ester of cholesterol.[1][2] It is formed from cholesterol by steroid sulfotransferases (SSTs) such as SULT2B1b (also known as cholesterol sulfotransferase)[2] and is converted back into cholesterol by steroid sulfatase (STS).[1] Accumulation of cholesterol sulfate in the skin is implicated in the pathophysiology of X-linked ichthyosis, a congenital disorder in which STS is non-functional and the body cannot convert cholesterol sulfate back into cholesterol.[1][2]

## See also[edit]

* Steroid sulfate

## References[edit]

1. ^ a b c Peter M. Elias (21 January 2016). Advances in Lipid Research: Skin Lipids. Elsevier. pp. 45–46. ISBN 978-1-4832-1545-7.
2. ^ a b c P. Itin; G. Jemec (15 September 2010). Ichthyoses. Karger Medical and Scientific Publishers. pp. 59–. ISBN 978-3-8055-9395-3.

* v
* t
* e

Endogenous steroids

Precursors|

* Cholesterol
* 22R-Hydroxycholesterol
* 20α,22R-Dihydroxycholesterol
* Pregnenolone
* 11β-Hydroxypregnenolone
* 17α-Hydroxypregnenolone
* 21-Hydroxypregnenolone
* 17α,21-Dihydroxypregnenolone
* 11β,17α,21-Trihydroxypregnenolone

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

|

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

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

|

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
* 4-Methoxyestrone
* 16α-Hydroxyestrone
* 16β-Hydroxyestrone
* 16-Ketoestradiol
* 16-Ketoestrone

* 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
* 2-Methoxyestriol
* 4-Methoxyestriol
* Estradiol disulfate
* Estradiol glucuronide
* Estradiol 3-glucuronide
* Estradiol 3-glucuronide 17β-sulfate
* Estradiol sulfate
* Estradiol 17β-sulfate
* Estrone glucuronide
* Estrone sulfate
* Estriol glucuronide
* Estriol sulfate
* Lipoidal estradiol (e.g., estradiol stearate, estradiol palmitate)

Progestogens|

* Progesterone
* 16α-Hydroxyprogesterone
* 17α-Hydroxyprogesterone
* 20α-Dihydroprogesterone
* 20β-Dihydroprogesterone
* 5α-Dihydroprogesterone
* 11-Deoxycorticosterone
* 5α-DHDOC

* Metabolites: Allopregnanediol
* Pregnanediol
* Pregnanediol glucuronide
* Pregnanetriol

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

Others|

* Vitamin D: 7-Dehydrocholesterol
* Calcidiol/Calcifediol
* Calcitriol
* Cholecalciferol

* Others: 7α-Hydroxycholesterol
* 11α-Hydroxyprogesterone
* 11β-Hydroxyprogesterone
* Cholesterol sulfate

* v
* t
* e

Cholesterol and steroid metabolic intermediates

Mevalonate pathway|

| to HMG-CoA|

* Acetyl-CoA
* Acetoacetyl-CoA
* HMB
* HMB-CoA
* HMG-CoA

|

Ketone bodies|

* Acetone
* Acetoacetic acid
* β-Hydroxybutyric acid

to DMAPP|

* Mevalonic acid
* Phosphomevalonic acid
* 5-Diphosphomevalonic acid
* Isopentenyl pyrophosphate
* Dimethylallyl pyrophosphate

Geranyl-|

* Geranyl pyrophosphate
* Geranylgeranyl pyrophosphate

Carotenoid|

* Prephytoene diphosphate
* Phytoene

Non-mevalonate pathway|

* DOXP
* MEP
* CDP-ME
* CDP-MEP
* MEcPP
* HMB-PP
* IPP
* DMAPP

To Cholesterol|

* Farnesyl pyrophosphate
* Squalene
* 2,3-Oxidosqualene
* Lanosterol

* Lanosterol
* 14-demethyllanosterol
* 4alpha-Methylzymosterol
* Zymosterone
* Zymosterol

* Zymosterol
* Zymostenol
* Lathosterol
* 7-Dehydrocholesterol
* Cholesterol

* Zymosterol
* Cholesta-7,24-dien-3-ol
* 7-Dehydrodesmosterol
* Desmosterol
* Cholesterol

From Cholesterol
to Steroid hormones|

* 22R-Hydroxycholesterol
* 20α,22R-Dihydroxycholesterol
* See here instead.

Nonhuman|

| To Sitosterol|

* Cycloartenol
* Cycloeucalenol
* Obtusifoliol
* 4α-methylfecosterol
* Isofucosterol
* 24-Methylenelophenol
* Sitosterol
* More Phytosterols see here instead.

|

To Ergocalciferol|

* Fecosterol
* Episterol
* Ergostatrienol
* Ergostatetraenol
* Ergosterol
* Ergocalciferol

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