ChemFOnt: Showing chemical card for 3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid (CFc000000267)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:37 UTC

Chemfont ID

CFc000000267

Molecule Identification

Common Name

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

Definition

3a.6b,7b,12a-tetrahydroxy-5b-cholan-24-oic is an unusual bile acid that has been identified in amniotic fluid and urine samples from adult patients with cholestatic liver disease. (PMID 2075618 ). 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3a,6b,7b,12a-Tetrahydroxy-5b-cholanoate	Generator
3a,6b,7b,12a-Tetrahydroxy-5b-cholanic acid	HMDB
(4R)-4-[(1S,2R,5R,7R,8S,9R,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,9R,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,9R,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

75110-48-4

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-KREOYVNCSA-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
7-alpha-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 (LMST04010121 )

Functional Ontology

Not Available

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000367)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000367)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000367)

Source

Endogenous

Endogenous (HMDB: HMDB0000367)

Animal

Animal (HMDB: HMDB0000367)

Exogenous

Food

Food (HMDB: HMDB0000367)

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: HMDB0000367)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000367)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000367)

Lipid metabolism pathway (HMDB: HMDB0000367)

Cellular process

Cell signaling (HMDB: HMDB0000367)

Biochemical process

Lipid transport (HMDB: HMDB0000367)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000367)

Molecular messenger

Signaling molecule (HMDB: HMDB0000367)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000367)

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	47.9 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

HMDB0000367

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021986

KNApSAcK ID

Not Available

Chemspider ID

4446988

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481262

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kagan, Henri B.; Jacques, Jean. Bile acids containing hydroxyls in position 6 and 7. Bull soc. chim. France (1960), 871-8.

Showing chemical card for 3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid (CFc000000267)

MOL for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

3D MOL for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

3D SDF for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

3D-SDF for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

PDB for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

3D PDB for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

SMILES for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

INCHI for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

Structure for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)

3D Structure for CFc000000267 (3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid)