ChemFOnt: Showing chemical card for 27alpha-Hydroxy-8-dehydrocholesterol (CFc000040587)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:42:09 UTC

Chemfont ID

CFc000040587

Molecule Identification

Common Name

27alpha-Hydroxy-8-dehydrocholesterol

Definition

This compound belongs to the family of Dihydroxy Bile Acids, Alcohols and Derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
27a-Hydroxy-8-dehydrocholesterol	Generator
27Α-hydroxy-8-dehydrocholesterol	Generator

Chemical Formula

C₂₇H₄₄O₂

Average Molecular Weight

400.6371

Monoisotopic Molecular Weight

400.334130652

IUPAC Name

(2S,5S,11S,14R,15R)-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),7-dien-5-ol

Traditional Name

(2S,5S,11S,14R,15R)-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),7-dien-5-ol

CAS Registry Number

Not Available

SMILES

C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3

InChI Identifier

InChI=1S/C27H44O2/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/h8,18-19,21,23-24,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,23-,24-,26+,27-/m1/s1

InChI Key

WGJXMUYDCGMVJH-VGABTXQKSA-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

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060132)

Source

Exogenous

Exogenous (HMDB: HMDB0060132)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0031 g/L	ALOGPS
logP	5.75	ALOGPS
logP	5.3	ChemAxon
logS	-5.1	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	123.05 m³·mol⁻¹	ChemAxon
Polarizability	50.34 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

HMDB0060132

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30778549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769840

PDB ID

Not Available

ChEBI ID

189990

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 27alpha-Hydroxy-8-dehydrocholesterol (CFc000040587)

MOL for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

3D MOL for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

3D SDF for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

3D-SDF for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

PDB for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

3D PDB for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

SMILES for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

INCHI for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

Structure for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)

3D Structure for CFc000040587 (27alpha-Hydroxy-8-dehydrocholesterol)