ChemFOnt: Showing chemical card for 3-Oxo-4,6-choladienoic acid (CFc000000361)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:44 UTC

Chemfont ID

CFc000000361

Molecule Identification

Common Name

3-Oxo-4,6-choladienoic acid

Definition

3-Oxo-4,6-choladienoic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-oxo-4,6-Choladienoate	Generator
3-oxo-4,6-Choladien-24-Oate	HMDB
3-oxo-4,6-Choladien-24-Oic acid	HMDB
3-Oxochola-4,6-dien-24-Oate	HMDB
(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-Dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoate	HMDB
3-oxo-4,6-Choladienoic acid	ChEBI

Chemical Formula

C₂₄H₃₄O₃

Average Molecular Weight

370.525

Monoisotopic Molecular Weight

370.250794954

IUPAC Name

(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoic acid

Traditional Name

3-oxo-4,6-choladienoic acid

CAS Registry Number

88179-71-9

SMILES

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

InChI Identifier

InChI=1S/C24H34O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5-6,14-15,18-21H,4,7-13H2,1-3H3,(H,26,27)/t15-,18+,19-,20+,21+,23+,24-/m1/s1

InChI Key

CREVIXFSUWYGRJ-IHMUCKAYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Bile acids, alcohols and derivatives

Alternative Parents

Substituents

Bile acid, alcohol, or derivatives
Oxosteroid
3-oxosteroid
Cyclohexenone
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010235 )

Functional Ontology

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

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

Excreta

Biofluid or Excreta

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

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000476)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000476)

Source

Endogenous

Endogenous (HMDB: HMDB0000476)

Animal

Animal (HMDB: HMDB0000476)

Exogenous

Food

Food (HMDB: HMDB0000476)

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: HMDB0000476)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000476)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000476)

Lipid metabolism pathway (HMDB: HMDB0000476)

Cellular process

Cell signaling (HMDB: HMDB0000476)

Biochemical process

Lipid transport (HMDB: HMDB0000476)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	4.19	ALOGPS
logP	4.82	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.81	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.6 m³·mol⁻¹	ChemAxon
Polarizability	43.86 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

HMDB0000476

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022063

KNApSAcK ID

Not Available

Chemspider ID

4447080

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5463

PubChem Compound

5283992

PDB ID

Not Available

ChEBI ID

88112

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Takehara, Jun; Fujiwara, Naoya; Endou, Kyouko; Kawai, Junya; Hosokawa, Akemi; Sumitani, Naoko. Process for production of steroids. PCT Int. Appl. (2007), 138pp.

Showing chemical card for 3-Oxo-4,6-choladienoic acid (CFc000000361)

MOL for CFc000000361 (3-Oxo-4,6-choladienoic acid)

3D MOL for CFc000000361 (3-Oxo-4,6-choladienoic acid)

3D SDF for CFc000000361 (3-Oxo-4,6-choladienoic acid)

3D-SDF for CFc000000361 (3-Oxo-4,6-choladienoic acid)

PDB for CFc000000361 (3-Oxo-4,6-choladienoic acid)

3D PDB for CFc000000361 (3-Oxo-4,6-choladienoic acid)

SMILES for CFc000000361 (3-Oxo-4,6-choladienoic acid)

INCHI for CFc000000361 (3-Oxo-4,6-choladienoic acid)

Structure for CFc000000361 (3-Oxo-4,6-choladienoic acid)

3D Structure for CFc000000361 (3-Oxo-4,6-choladienoic acid)