ChemFOnt: Showing chemical card for 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid (CFc000000385)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:45 UTC

Chemfont ID

CFc000000385

Molecule Identification

Common Name

7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid

Definition

7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid, also known as 3-dehydrochenodeoxycholic acid or (5beta,7alpha)-7-hydroxy-3-oxocholan-24-oate, is classified as a monohydroxy bile acids, alcohol or a monohydroxy bile acids, alcohol derivative. Monohydroxy bile acids, alcohols are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid is considered to be practically insoluble (in water) and acidic. 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid is a bile acid lipid molecule. Glycine- and taurine-conjugated 7alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid has been identified in normal human serum (PMID: 1939467 ) and as a cholesterol metabolite in bile acids produced in HepG2 cells, a well-differentiated human hepatoblastoma cell line (PMID: 1655725 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7a-Hydroxy-3-oxo-5b-cholanoate	Generator
(5b,7a)-7-Hydroxy-3-oxo-cholan-24-Oate	HMDB
(5b,7a)-7-Hydroxy-3-oxo-cholan-24-Oic acid	HMDB

Chemical Formula

C₂₄H₃₈O₄

Average Molecular Weight

390.5561

Monoisotopic Molecular Weight

390.277009704

IUPAC Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,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,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@@](C)(CCC(O)=O)C1([H])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

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-KXIRRPOASA-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

Not Available

Functional Ontology

Cellular substructure

Extracellular (HMDB: HMDB0000503)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31643938)
Bile (PMID: 31643938)

Excreta

Biofluid or Excreta

Feces (PMID: 31643938)
Urine (PMID: 1112456)

Source

Exogenous

Exogenous (HMDB: HMDB0000503)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000503)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

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	45.37 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022081

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

53477698

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Riva, Sergio; Bovara, Roberto; Zetta, Lucia; Pasta, Piero; Ottolina, Gianluca; Carrea, Giacomo. Enzymic a/b inversion of C-3 hydroxyl of bile acids and study of the effects of organic solvents on reaction rates. Journal of Organic Chemistry (1988), 53(1), 88-92.

Showing chemical card for 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid (CFc000000385)

MOL for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D MOL for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D SDF for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D-SDF for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

PDB for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D PDB for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

SMILES for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

INCHI for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

Structure for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D Structure for CFc000000385 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)