ChemFOnt: Showing chemical card for 3a,4b,7a-Trihydroxy-5b-cholanoic acid (CFc000000224)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:34 UTC

Chemfont ID

CFc000000224

Molecule Identification

Common Name

3a,4b,7a-Trihydroxy-5b-cholanoic acid

Definition

3a,4b,7a-Trihydroxy-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. 3a,4b,7a-Trihydroxy-5b-cholanoic acid accounts for 5-15% of the total biliary bile acids in early gestation, has been identified in the feces from healthy newborn infants many days after birth, indicating a hepatic origin for C-4 hydroxylation of bile acids. PMID 2794778 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3a,4b,7a-Trihydroxy-5b-cholanoate	Generator
3,4,7-Trihydroxycholanoate	HMDB
3,4,7-Trihydroxycholanoic acid	HMDB
3a,4b,7a-Trihydroxy-5b-cholan-24-Oate	HMDB
3a,4b,7a-Trihydroxy-5b-cholan-24-Oic acid	HMDB
3alpha,4beta,7alpha-Trihydroxy-5beta-cholan-24-Oate	HMDB
3alpha,4beta,7alpha-Trihydroxy-5beta-cholan-24-Oic acid	HMDB
3alpha,4beta,7alpha-Trihydroxy-5beta-cholanoate	HMDB
3alpha,4beta,7alpha-Trihydroxy-5beta-cholanoic acid	HMDB
3 alpha,4 beta,7 alpha-Trihydroxy-5 beta-cholanoic acid	HMDB
3,4,7-TCOA	HMDB
(4S)-4-[(1S,2R,5R,6R,7S,9R,10S,11S,15R)-5,6,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

IUPAC Name

(4S)-4-[(1S,2R,5R,6R,7S,9R,10S,11S,15R)-5,6,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

3,4,7-trihydroxycholanoic acid

CAS Registry Number

117590-81-5

SMILES

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

InChI Identifier

InChI=1S/C24H40O5/c1-13(4-7-20(27)28)14-5-6-15-21-16(8-10-23(14,15)2)24(3)11-9-18(25)22(29)17(24)12-19(21)26/h13-19,21-22,25-26,29H,4-12H2,1-3H3,(H,27,28)/t13-,14?,15-,16-,17+,18+,19+,21-,22+,23+,24+/m0/s1

InChI Key

AIHWGPJJINPTRP-VSASKLEVSA-N

Chemical Taxonomy

Description

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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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: HMDB0000320)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000320)

Source

Endogenous

Endogenous (HMDB: HMDB0000320)

Animal

Animal (HMDB: HMDB0000320)

Exogenous

Food

Food (HMDB: HMDB0000320)

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: HMDB0000320)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000320)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000320)

Lipid metabolism pathway (HMDB: HMDB0000320)

Cellular process

Cell signaling (HMDB: HMDB0000320)

Biochemical process

Lipid transport (HMDB: HMDB0000320)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.068 g/L	ALOGPS
logP	2.11	ALOGPS
logP	2.72	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.56 m³·mol⁻¹	ChemAxon
Polarizability	47.05 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

HMDB0000320

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021946

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

5309

PubChem Compound

53477681

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Dumaswala R; Setchell K D; Zimmer-Nechemias L; Iida T; Goto J; Nambara T Identification of 3 alpha,4 beta,7 alpha-trihydroxy-5 beta-cholanoic acid in human bile: reflection of a new pathway in bile acid metabolism in humans. Journal of lipid research (1989), 30(6), 847-56.

Showing chemical card for 3a,4b,7a-Trihydroxy-5b-cholanoic acid (CFc000000224)

MOL for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

3D MOL for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

3D SDF for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

3D-SDF for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

PDB for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

3D PDB for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

SMILES for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

INCHI for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

Structure for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)

3D Structure for CFc000000224 (3a,4b,7a-Trihydroxy-5b-cholanoic acid)