ChemFOnt: Showing chemical card for 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid (CFc000000341)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:42 UTC

Chemfont ID

CFc000000341

Molecule Identification

Common Name

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid

Definition

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid is an unusual bile acids that have been detected in urine early in life, especially during the period up to 1 mo of age. This indicate that bile acid synthesis and metabolism in the liver of developing infants is significantly different from that occurring in the liver of adults. (PMID 10203155 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7alpha,12alpha-Dihydroxy-3-oxochol-4-enoate	ChEBI
7alpha,12alpha-Dihydroxy-3-oxochol-4-enoic acid	ChEBI
7a,12a-Dihydroxy-3-oxochol-4-enoate	Generator
7a,12a-Dihydroxy-3-oxochol-4-enoic acid	Generator
7Α,12α-dihydroxy-3-oxochol-4-enoate	Generator
7Α,12α-dihydroxy-3-oxochol-4-enoic acid	Generator
7a,12a-Dihydroxy-3-oxo-4-cholenoate	Generator
7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oate	HMDB
7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oic acid	HMDB
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-Dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₃₆O₅

Average Molecular Weight

404.5396

Monoisotopic Molecular Weight

404.256274262

IUPAC Name

(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

CAS Registry Number

13587-11-6

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C24H36O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h10,13,16-20,22,26-27H,4-9,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChI Key

ZZUMXQCSMJCDDC-DFQOQHGMSA-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
3-oxo-delta-4-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
12-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

7alpha-hydroxy steroid (CHEBI:49269 )
3-oxo Delta(4)-steroid (CHEBI:49269 )
12alpha-hydroxy steroid (CHEBI:49269 )
C24 bile acids, alcohols, and derivatives (LMST04010241 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000447)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000447)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000447)

Source

Endogenous

Endogenous (HMDB: HMDB0000447)

Animal

Animal (HMDB: HMDB0000447)

Exogenous

Food

Food (HMDB: HMDB0000447)

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)

Exogenous (HMDB: HMDB0000447)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000447)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000447)

Lipid metabolism pathway (HMDB: HMDB0000447)

Cellular process

Cell signaling (HMDB: HMDB0000447)

Biochemical process

Lipid transport (HMDB: HMDB0000447)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000447)

Molecular messenger

Signaling molecule (HMDB: HMDB0000447)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000447)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	2.17	ALOGPS
logP	2.64	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.59 m³·mol⁻¹	ChemAxon
Polarizability	45.67 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

HMDB0000447

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022052

KNApSAcK ID

Not Available

Chemspider ID

4447084

KEGG Compound ID

C15568

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5436

PubChem Compound

5283996

PDB ID

Not Available

ChEBI ID

49269

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kallner, Anders. Bile acids and steroids. 182. A method of synthesis of allochlanoic acids. Acta Chemica Scandinavica (1947-1973) (1967), 21(2), 322-8.

Showing chemical card for 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid (CFc000000341)

MOL for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D MOL for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D SDF for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D-SDF for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

PDB for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D PDB for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

SMILES for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

INCHI for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

Structure for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D Structure for CFc000000341 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)