ChemFOnt: Showing chemical card for 26-hydroxycholesterol (CFc000042740)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:24 UTC

Chemfont ID

CFc000042740

Molecule Identification

Common Name

26-hydroxycholesterol

Definition

26-hydroxycholesterol, also known as Cholest-5-ene-3beta,27-diol or (3 beta,25R)-Cholest-5-ene-3,26-diol, is classified as a dihydroxy bile acids, alcohol or a Dihydroxy bile acids, alcohol derivative. Dihydroxy bile acids, alcohols are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. 26-hydroxycholesterol is considered to be practically insoluble (in water) and relatively neutral. 26-hydroxycholesterol can be synthesized from cholesterol. 26-hydroxycholesterol can be synthesized into 26-hydroxycholesterol 3-sulfate. 26-hydroxycholesterol is a sterol lipid molecule

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
27-Hydroxycholesterol	ChEBI
Cholest-5-ene-3beta,26-diol	ChEBI
Cholest-5-ene-3beta,27-diol	ChEBI
Cholest-5-ene-3b,26-diol	Generator
Cholest-5-ene-3β,26-diol	Generator
Cholest-5-ene-3b,27-diol	Generator
Cholest-5-ene-3β,27-diol	Generator
(25R)-Cholest-5-ene-3 beta,26-diol	MeSH
5-Cholestene-3 beta,27-diol	MeSH
(3 beta,25R)-Cholest-5-ene-3,26-diol	MeSH
26-Hydroxycholesterol, (25R)	MeSH
(25R)-26-Hydroxycholesterol	MeSH
Cholest-5-ene-3 beta,27-diol	MeSH

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.663

Monoisotopic Molecular Weight

402.349780721

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

13095-61-9

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CO

InChI Identifier

InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18?,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

FYHRJWMENCALJY-CCDZVGGQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-5-steroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

26-hydroxy steroid (CHEBI:17703 )
oxysterol (CHEBI:17703 )
Cholesterol and derivatives (C15610 )
Cholesterol and derivatives (LMST01010057 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062328)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00021 g/L	ALOGPS
logP	6.21	ALOGPS
logP	5.75	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.47 m³·mol⁻¹	ChemAxon
Polarizability	51.61 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

External Links

HMDB ID

HMDB0062328

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C15610

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99470

PDB ID

Not Available

ChEBI ID

17703

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 26-hydroxycholesterol (CFc000042740)

MOL for CFc000042740 (26-hydroxycholesterol)

3D MOL for CFc000042740 (26-hydroxycholesterol)

3D SDF for CFc000042740 (26-hydroxycholesterol)

3D-SDF for CFc000042740 (26-hydroxycholesterol)

PDB for CFc000042740 (26-hydroxycholesterol)

3D PDB for CFc000042740 (26-hydroxycholesterol)

SMILES for CFc000042740 (26-hydroxycholesterol)

INCHI for CFc000042740 (26-hydroxycholesterol)

Structure for CFc000042740 (26-hydroxycholesterol)

3D Structure for CFc000042740 (26-hydroxycholesterol)