Bovine Metabolome Database: Showing metabocard for Cholesterol sulfate (BMDB0000653)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:21 UTC

Update Date

2020-05-11 20:44:01 UTC

BMDB ID

BMDB0000653

Secondary Accession Numbers

BMDB00653

Metabolite Identification

Common 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₂₇H₄₆O₄S

Average Molecular Weight

466.717

Monoisotopic Molecular Weight

466.31168065

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

Traditional 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

CAS Registry Number

1256-86-6

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

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

Chemical Taxonomy

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

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-2117900000-d2dc1d52c2c6b6024f0f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-014i-0000900000-548706c8c2ce9f09a548	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-014i-0000900000-7a511fae1b9c9c3ae716	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-014i-1000900000-c804c1920be98c205e26	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0004900000-3e084b0869dec1511e5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2019000000-7af1b592431ae5367f0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-7259200000-0958e602876ec6735f35	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0002900000-4bf9e43838ae87b48760	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-1009200000-cefbd199aabf735755c7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0159-5009000000-5d0bf7cb45e64f0239da	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-e3ecb40a540de289ba8b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1000900000-76ef4296ff8273921824	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9002600000-9ad23ecad6099c20e148	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0002900000-b9275f9e554fed1edbf3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ar0-3279000000-9c38d5fd98e2387d950d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3494000000-282974a841618bfa049a	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Biospecimen Locations

Adrenal Gland
Epidermis
Platelet

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000653

DrugBank ID

DB01990

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

41321

References

Synthesis Reference

Drayer, N. M.; Lieberman, S. Isolation of cholesterol sulfate from human blood and gallstones. Biochemical and Biophysical Research Communications (1965), 18(1), 126-30.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Cholesterol sulfate (BMDB0000653)

Structure for BMDB0000653 (Cholesterol sulfate)