Showing Compound Cholesterol sulfate (FDB022164)

Record Information

Version

1.0

Creation date

2011-09-21 00:09:24 UTC

Update date

2015-10-09 22:29:50 UTC

Primary ID

FDB022164

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cholesterol sulfate

Description

Cholesterol sulfate belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Based on a literature review a significant number of articles have been published on Cholesterol sulfate.

CAS Number

1256-86-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
CHOLEST-5-en-3-yl hydrogen sulfATE	ChEBI
Cholest-5-en-3beta-ol sulfate	ChEBI
Cholesterol 3-sulfate	ChEBI
Cholesterol 3-sulphate	ChEBI
Cholesterol hydrogen sulfate	ChEBI
Cholesterol hydrogen sulphate	ChEBI
Cholesterol sulphate	ChEBI
Cholesteryl sulfate	ChEBI
Cholesteryl sulphate	ChEBI
CHOLEST-5-en-3-yl hydrogen sulfuric acid	Generator
CHOLEST-5-en-3-yl hydrogen sulphate	Generator
CHOLEST-5-en-3-yl hydrogen sulphuric acid	Generator
Cholest-5-en-3b-ol sulfate	Generator
Cholest-5-en-3b-ol sulfuric acid	Generator
Cholest-5-en-3b-ol sulphate	Generator
Cholest-5-en-3b-ol sulphuric acid	Generator
Cholest-5-en-3beta-ol sulfuric acid	Generator
Cholest-5-en-3beta-ol sulphate	Generator
Cholest-5-en-3beta-ol sulphuric acid	Generator
Cholest-5-en-3β-ol sulfate	Generator
Cholest-5-en-3β-ol sulfuric acid	Generator
Cholest-5-en-3β-ol sulphate	Generator
Cholest-5-en-3β-ol sulphuric acid	Generator
Cholesterol 3-sulfuric acid	Generator
Cholesterol 3-sulphuric acid	Generator
Cholesterol hydrogen sulfuric acid	Generator
Cholesterol hydrogen sulphuric acid	Generator
Cholesterol sulfuric acid	Generator
Cholesterol sulphuric acid	Generator
Cholesteryl sulfuric acid	Generator
Cholesteryl sulphuric acid	Generator
5-Cholesten-3b-yl sulfate	HMDB
5-Cholesten-3b-yl sulphate	HMDB
Cholesteryl sulfate, sodium salt, (3beta)-isomer	MeSH, HMDB
Cholesteryl sulfate, ammonium salt, (3beta)-isomer	MeSH, HMDB
Cholesteryl sulfate, sodium salt, 26-(14)C-labeled	MeSH, HMDB
Cholesteryl sulfate, 3H-labeled, (3beta)-isomer	MeSH, HMDB
Cholesteryl sulfate, potassium salt, (3beta)-isomer	MeSH, HMDB
Cholesterol sulfate	hmdb
Cholesterol sulfic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	7.5e-05 g/L	ALOGPS
logP	3.27	ALOGPS
logP	7.17	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.61 m³·mol⁻¹	ChemAxon
Polarizability	56.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C27H46O4S

IUPAC name

[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

InChI Identifier

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

InChI Key

BHYOQNUELFTYRT-DPAQBDIFSA-N

Isomeric SMILES

[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O

Average Molecular Weight

466.717

Monoisotopic Molecular Weight

466.31168065

Classification

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol
Sulfated steroid skeleton
Delta-5-steroid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:41321 )
Sulfates (LMST05020016 )

Ontology

Ingestion

Source:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Multicellular process:

Inflammatory response

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cholesterol sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udr-2117900000-d2dc1d52c2c6b6024f0f	Spectrum
Predicted GC-MS	Cholesterol sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-014i-0000900000-548706c8c2ce9f09a548	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-014i-0000900000-7a511fae1b9c9c3ae716	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-014i-1000900000-c804c1920be98c205e26	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0004900000-3e084b0869dec1511e5a	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2019000000-7af1b592431ae5367f0f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-7259200000-0958e602876ec6735f35	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0002900000-4bf9e43838ae87b48760	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-1009200000-cefbd199aabf735755c7	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0159-5009000000-5d0bf7cb45e64f0239da	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-e3ecb40a540de289ba8b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1000900000-76ef4296ff8273921824	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9002600000-9ad23ecad6099c20e148	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0002900000-b9275f9e554fed1edbf3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ar0-3279000000-9c38d5fd98e2387d950d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3494000000-282974a841618bfa049a	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		Spectrum