ChemFOnt: Showing chemical card for 3a,7a-Dihydroxycholanoic acid (CFc000000283)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:38 UTC

Chemfont ID

CFc000000283

Molecule Identification

Common Name

3a,7a-Dihydroxycholanoic acid

Definition

3a,7a-Dihydroxycholanoic acid is a chenodeoxycholic or bile acid present in human blood serum. (PMID 13324110 ) and in the biliary excretion of patients with choledochostomy drainage (PMID 16695472 ). 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,7a-Dihydroxycholanoate	Generator
(3a,7a)-3,7-Dihydroxy-cholan-24-Oate	HMDB
(3a,7a)-3,7-Dihydroxy-cholan-24-Oic acid	HMDB
3a,7a-Dihydroxy-cholanoate	HMDB
3a,7a-Dihydroxy-cholanoic acid	HMDB
(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

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

Traditional Name

3a,7a-dihydroxycholanoate

CAS Registry Number

30634-99-2

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15?,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

InChI Key

RUDATBOHQWOJDD-BYRKYSOESA-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-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000384)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000384)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000384)

Source

Endogenous

Endogenous (HMDB: HMDB0000384)

Animal

Animal (HMDB: HMDB0000384)

Exogenous

Food

Food (HMDB: HMDB0000384)

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: HMDB0000384)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000384)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000384)

Lipid metabolism pathway (HMDB: HMDB0000384)

Cellular process

Cell signaling (HMDB: HMDB0000384)

Biochemical process

Lipid transport (HMDB: HMDB0000384)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000384)

Molecular messenger

Signaling molecule (HMDB: HMDB0000384)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000384)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.01	ALOGPS
logP	3.71	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.27 m³·mol⁻¹	ChemAxon
Polarizability	46.57 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

HMDB0000384

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022002

KNApSAcK ID

Not Available

Chemspider ID

13628074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5373

PubChem Compound

21252245

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Berner, E.; Lardon, A.; Reichstein, T. Bile acids and related compounds. XLV. 3(a),12(a)-Dihydroxy-7-cholenic acid. Helvetica Chimica Acta (1947), 30 1542-53.

Showing chemical card for 3a,7a-Dihydroxycholanoic acid (CFc000000283)

MOL for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

3D MOL for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

3D SDF for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

3D-SDF for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

PDB for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

3D PDB for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

SMILES for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

INCHI for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

Structure for CFc000000283 (3a,7a-Dihydroxycholanoic acid)

3D Structure for CFc000000283 (3a,7a-Dihydroxycholanoic acid)