ChemFOnt: Showing chemical card for 3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid (CFc000000298)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:39 UTC

Chemfont ID

CFc000000298

Molecule Identification

Common Name

3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid

Definition

3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. 3 alpha,6 alpha,7 alpha,12 alpha-Tetrahydroxy-5 beta-cholan-24-oic acid has been identified from human meconium and healthy neonatal urine. (PMID 2743505 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3a,6b,7a,12a-Tetrahydroxy-5b-cholanoate	Generator
(4R)-4-[(1S,2R,5R,7R,8S,9S,10R,11S,14R,15R,16S)-5,8,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	Generator, HMDB

Chemical Formula

C₂₄H₄₀O₆

Average Molecular Weight

424.5708

Monoisotopic Molecular Weight

424.282489012

IUPAC Name

(4R)-4-[(1S,2R,5R,7R,8S,9S,10R,11S,14R,15R,16S)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,5R,7R,8S,9S,10R,11S,14R,15R,16S)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

CAS Registry Number

80875-93-0

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)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C24H40O6/c1-12(4-7-19(27)28)14-5-6-15-20-16(11-18(26)24(14,15)3)23(2)9-8-13(25)10-17(23)21(29)22(20)30/h12-18,20-22,25-26,29-30H,4-11H2,1-3H3,(H,27,28)/t12-,13-,14-,15+,16+,17+,18+,20+,21+,22+,23-,24-/m1/s1

InChI Key

COCMFMBNEAMQMA-VGKGADPCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl 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

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Tetrahydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010120 )

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: HMDB0000399)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000399)

Source

Endogenous

Endogenous (HMDB: HMDB0000399)

Animal

Animal (HMDB: HMDB0000399)

Exogenous

Food

Food (HMDB: HMDB0000399)

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: HMDB0000399)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000399)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000399)

Lipid metabolism pathway (HMDB: HMDB0000399)

Cellular process

Cell signaling (HMDB: HMDB0000399)

Biochemical process

Lipid transport (HMDB: HMDB0000399)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
logP	1.33	ALOGPS
logP	1.49	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.07 m³·mol⁻¹	ChemAxon
Polarizability	47.77 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

HMDB0000399

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022016

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

139419

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kurosawa, Takao; Mahara, Reijiro; Nittono, Hiroshi; Tohma, Masahiko. Synthesis of 6-hydroxylated bile acids and identification of 3a,6a,7a,12a-tetrahydroxy-5b-cholan-24-oic acid in human meconium and neonatal urine. Chemical & Pharmaceutical Bulletin (1989), 37(2), 557-9.

Showing chemical card for 3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid (CFc000000298)

MOL for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

3D MOL for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

3D SDF for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

3D-SDF for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

PDB for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

3D PDB for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

SMILES for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

INCHI for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

Structure for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)

3D Structure for CFc000000298 (3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid)