Cholesterol sulfate

HCID 65076
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Basic information

CAS
1256-86-6
Standard SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
BHYOQNUELFTYRT-DPAQBDIFSA-N
Molecular formula
C27H46O4S
Average molar mass
466.7 g/mol
Monoisotopic mass
466.31168095

Overview

Cholesterol sulfate is a steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3. It has a role as a human metabolite. It is functionally related to a cholesterol. It is a conjugate acid of a cholesterol sulfate(1-).

Names & identifiers

Preferred name
Cholesterol sulfate
IUPAC
[(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
English name
Cholesterol sulfate
Molecular formula
C27H46O4S
Molecular weight
466.72

Names & synonyms

Cholesterol sulfateCholesteryl sulfate1256-86-6Cholesterol 3-sulfatecholesterol sulphateCholest-5-en-3beta-ol sulfateCholesterol hydrogen sulfatecholesteryl sulphatecholest-5-en-3beta-yl hydrogen sulfateCholesterol 3-sulphateCholesterol hydrogen sulphateKU576NT9O9
Show more names
3β-Cholesteryl sulfateCholesterol sulfuric acidCholesterol 3-sulfuric acidCholesterol Sulfate Triethylamine SaltCholest-5-en-3-ol (3β)-, hydrogen sulfate(3beta)-Cholest-5-en-3-ol hydrogen sulfatesulfuric acid [(3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] ester
[(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 sulfateDTXSID401016822Cholest-5-en-3-ol (3beta)-, hydrogen sulfateCHEBI:41321((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 sulfateRefChem:125691DTXCID001475012CHOLEST-5-EN-3-YL HYDROGEN SULFATE

Database identifiers

CAS
1256-86-6、2864-50-8
PubChem CID
65076
DTXSID
DTXSID401016822
ChEMBL
CHEMBL1231592
ChEBI
CHEBI:41321
UNII
KU576NT9O9
Nikkaji
J324.075D

Properties

Computed structural properties

XLogP
8.2
Topological polar surface area
72 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
7
Heavy atoms
32

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Sulfates [ST0502]
Physical DescriptionSolid
Collision Cross Section237.01 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Density
1.12 · 1.12±0.1 g/cm3(Predicted)
pka
-3.51 · -3.51±0.18(Predicted)
FDA UNII
576 NT9O9 · KU576NT9O9

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES.

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.

Tissue LocationsAdrenal Gland
Cellular LocationsCytoplasm

Applications

UsesCholesterol sulfate is a DOCK2 inhibitor. Cholesterol sulfate has an IC50 value of 2 μM for mouse DOCK2. Cholesterol sulfate can be used in studies such as immunity and inflammation[1].

Upstream & downstream products

Upstream raw materials

Suppliers16 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
湖北瑞玛标物科技有限公司15787879035 15787875101 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
TargetMol 中国（陶术生物）400-821-0310 15002144251 · [email protected]

Additional notes

DefinitionChEBI: A steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3.

Related reactions

2 records
New reaction record

Compound notes

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