ChemFOnt: Showing chemical card for 7a-Hydroxy-3-oxo-5b-cholanoic acid (CFc000043208)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:46:10 UTC

Chemfont ID

CFc000043208

Molecule Identification

Common Name

7a-Hydroxy-3-oxo-5b-cholanoic acid

Definition

7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid, also known as 3-dehydrochenodeoxycholic acid or (5b,7a)-7-hydroxy-3-oxocholan-24-oate, is a member of the class of compounds known as monohydroxy bile acids, alcohols, and derivatives. These compounds are bile acids, alcohols, or any of their derivatives bearing a hydroxyl group. Thus, 7alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid is considered to be a bile acid lipid molecule. 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5beta,7alpha)-7-Hydroxy-3-oxocholan-24-Oic acid	ChEBI
3-Dehydrochenodeoxycholic acid	ChEBI
3-Oxochenodeoxycholic acid	ChEBI
Dehydrochenodeoxycholic acid	ChEBI
(5b,7a)-7-Hydroxy-3-oxocholan-24-Oate	Generator
(5b,7a)-7-Hydroxy-3-oxocholan-24-Oic acid	Generator
(5beta,7alpha)-7-Hydroxy-3-oxocholan-24-Oate	Generator
(5Β,7α)-7-hydroxy-3-oxocholan-24-Oate	Generator
(5Β,7α)-7-hydroxy-3-oxocholan-24-Oic acid	Generator
3-Dehydrochenodeoxycholate	Generator
3-Oxochenodeoxycholate	Generator
Dehydrochenodeoxycholate	Generator
7a-Hydroxy-3-oxo-5b-cholan-24-Oate	Generator
7a-Hydroxy-3-oxo-5b-cholan-24-Oic acid	Generator
7alpha-Hydroxy-3-oxo-5beta-cholan-24-Oate	Generator
7Α-hydroxy-3-oxo-5β-cholan-24-Oate	Generator
7Α-hydroxy-3-oxo-5β-cholan-24-Oic acid	Generator
7α-Hydroxy-3-oxo-5β-cholanic acid	HMDB
3-Oxo-7α-hydroxy-5β-cholanic acid	HMDB
3-Oxo-7α-hydroxycholan-24-oic acid	HMDB
3-keto-7α-Hydroxy-5β-cholanic acid	HMDB
7α-Hydroxy-3-oxo-5β-cholanoic acid	HMDB
7a-Hydroxy-3-oxo-5b-cholanoic acid	HMDB
7alpha-Hydroxy-3-oxo-5beta-cholanoic acid	HMDB
(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	Generator, HMDB

Chemical Formula

C₂₄H₃₈O₄

Average Molecular Weight

390.564

Monoisotopic Molecular Weight

390.277009704

IUPAC Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

4185-00-6

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17-,18+,19+,20-,22+,23+,24-/m1/s1

InChI Key

KNVADAPHVNKTEP-CIGXQKLNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
3-oxosteroid
Hydroxysteroid
Oxosteroid
7-hydroxysteroid
3-oxo-5-beta-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010161 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062796)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	3.11	ALOGPS
logP	3.92	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.25 m³·mol⁻¹	ChemAxon
Polarizability	45.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062796

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283932

PDB ID

Not Available

ChEBI ID

88097

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 7a-Hydroxy-3-oxo-5b-cholanoic acid (CFc000043208)

MOL for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

3D MOL for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

3D SDF for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

3D-SDF for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

PDB for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

3D PDB for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

SMILES for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

INCHI for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

Structure for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

3D Structure for CFc000043208 (7a-Hydroxy-3-oxo-5b-cholanoic acid)