ChemFOnt: Showing chemical card for 3beta,7alpha-Dihydroxy-5-cholestenoate (CFc000007979)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:34 UTC

Chemfont ID

CFc000007979

Molecule Identification

Common Name

3beta,7alpha-Dihydroxy-5-cholestenoate

Definition

3beta,7alpha-Dihydroxy-5-cholestenoate is found in the primary bile acid biosynthesis pathway. It is created from 3beta-Hydroxy-5-cholestenoate through the action of CYP7B (E1.14.13.100). 3beta,7alpha-Dihydroxy-5-cholestenoate is then converted into 7alpha-Hydroxy-3-oxo-4-cholestenoate by the action of HSD3B7 (EC:1.1.1.181).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3b,7a-Dihydroxy-5-cholestenoate	Generator
3b,7a-Dihydroxy-5-cholestenoic acid	Generator
3beta,7alpha-Dihydroxy-5-cholestenoic acid	Generator
3Β,7α-dihydroxy-5-cholestenoate	Generator
3Β,7α-dihydroxy-5-cholestenoic acid	Generator
(3beta,7alpha)-3,7-Dihydroxy-cholest-5-en-26-Oate	HMDB
(3beta,7alpha)-3,7-Dihydroxy-cholest-5-en-26-Oic acid	HMDB
3 beta,7 alpha-Dihydroxy-5-cholesten-26-Oate	HMDB
3 beta,7 alpha-Dihydroxy-5-cholesten-26-Oic acid	HMDB
3,7-Dihydroxy-5-cholestenoate	HMDB
3,7-Dihydroxy-5-cholestenoic acid	HMDB
3beta,7alpha-Dihydroxy-5-cholesten-26-Oate	HMDB
3beta,7alpha-Dihydroxy-5-cholesten-26-Oic acid	HMDB

Chemical Formula

C₂₇H₄₄O₄

Average Molecular Weight

432.6359

Monoisotopic Molecular Weight

432.323959896

IUPAC Name

(6R)-6-[(2R,5S,9S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid

Traditional Name

(6R)-6-[(2R,5S,9S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid

CAS Registry Number

115538-84-6

SMILES

C[C@H](CCCC(C)C(O)=O)C1CCC2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C27H44O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h15-17,19-24,28-29H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20?,21?,22?,23-,24?,26+,27-/m1/s1

InChI Key

GYJSAWZGYQXRBS-BJGNZVHYSA-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

Dihydroxy bile acid, alcohol, or derivatives
Steroid acid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
7-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
Delta-5-steroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9818927)

Cellular substructure

Extracellular (HMDB: HMDB0012454)
Membrane (HMDB: HMDB0012454)

Source

Exogenous

Exogenous (HMDB: HMDB0012454)

Endogenous

Endogenous (HMDB: HMDB0012454)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Bile Acid Biosynthesis (HMDB: HMDB0012454)

Disease pathway

Zellweger Syndrome (HMDB: HMDB0012454)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0069 g/L	ALOGPS
logP	3.92	ALOGPS
logP	4.9	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.75 m³·mol⁻¹	ChemAxon
Polarizability	51.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029070

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481408

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3beta,7alpha-Dihydroxy-5-cholestenoate (CFc000007979)

MOL for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D MOL for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D SDF for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D-SDF for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

PDB for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D PDB for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

SMILES for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

INCHI for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

Structure for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)

3D Structure for CFc000007979 (3beta,7alpha-Dihydroxy-5-cholestenoate)