ChemFOnt: Showing chemical card for 3a,6b,7b-Trihydroxy-5b-cholanoic acid (CFc000000314)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:40 UTC

Chemfont ID

CFc000000314

Molecule Identification

Common Name

3a,6b,7b-Trihydroxy-5b-cholanoic acid

Definition

3a,6b,7b-Trihydroxy-5b-cholanoic acid, also known as beta-muricholic acid, is a bile acid. 3a,6b,7b-Trihydroxy-5b-cholanoic acid belongs to the class of compounds known muricholic acids in which the hydroxy groups at positions 6 and 7 both have a beta configuration. It is also classified as a 6beta-hydroxy steroid, a 7beta-hydroxy steroid, a steroid acid and a bile acid. Muricholic acids are a group of bile acids that are particularly abundant in mice, which gives them their name. Muricholic acids are also found at low concentrations in other mammalian species, including humans (PMID: 12543708 ). Muricholic acids differ from the primary bile acids found in humans (which are cholic acid and chenodeoxycholic acid) by having a hydroxyl group in the beta-conformation at the 6-position. The orientation of the hydroxyl group at the 7 position defines alpha- or beta-muricholic acid. Muricholic acids are detectable at low concentrations in human urine (PMIDL 1629271). The enzyme responsible for the 6-hydroxylation reactions forming muricholates in rodents is the cytochrome P450 Cyp2c70. This produces alpha-muricholic acid from chenodeoxycholic acid, and beta-muricholic acid from ursodeoxycholic acid. Bile acids, such as muricholic acid, 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, 6, 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
(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oic acid	ChEBI
3,6,7-Trihydroxy-5beta-cholan-24-Oic acid	ChEBI
5beta-Cholanic acid-3alpha,6beta,7beta-triol	ChEBI
beta-MCA	ChEBI
beta-Muricholic acid	Kegg
3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oic acid	Kegg
(3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oate	Generator
(3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oate	Generator
(3Α,5β,6β,7β)-3,6,7-trihydroxycholan-24-Oate	Generator
(3Α,5β,6β,7β)-3,6,7-trihydroxycholan-24-Oic acid	Generator
3,6,7-Trihydroxy-5b-cholan-24-Oate	Generator
3,6,7-Trihydroxy-5b-cholan-24-Oic acid	Generator
3,6,7-Trihydroxy-5beta-cholan-24-Oate	Generator
3,6,7-Trihydroxy-5β-cholan-24-Oate	Generator
3,6,7-Trihydroxy-5β-cholan-24-Oic acid	Generator
5b-Cholanate-3a,6b,7b-triol	Generator
5b-Cholanic acid-3a,6b,7b-triol	Generator
5beta-Cholanate-3alpha,6beta,7beta-triol	Generator
5Β-cholanate-3α,6β,7β-triol	Generator
5Β-cholanic acid-3α,6β,7β-triol	Generator
b-MCA	Generator
Β-mca	Generator
b-Muricholate	Generator
b-Muricholic acid	Generator
beta-Muricholate	Generator
Β-muricholate	Generator
Β-muricholic acid	Generator
3a,6b,7b-Trihydroxy-5b-cholan-24-Oate	Generator
3a,6b,7b-Trihydroxy-5b-cholan-24-Oic acid	Generator
3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oate	Generator
3Α,6β,7β-trihydroxy-5β-cholan-24-Oate	Generator
3Α,6β,7β-trihydroxy-5β-cholan-24-Oic acid	Generator
3a,6b,7b-Trihydroxy-5b-cholanoate	Generator
3a,6b,7b-Trihydroxy-5b-cholanate	HMDB
3a,6b,7b-Trihydroxy-5b-cholanic acid	HMDB
3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid	HMDB
3,6,7-Trihydroxy-5-cholanoic acid	HMDB
alpha-Muricholic acid	HMDB
Hyocholic acid	HMDB
Muricholic acid	HMDB
Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6beta,7beta)-isomer	HMDB
Muricholic acid, sodium salt	HMDB
Omega-muricholic acid	HMDB
Trihydroxy-5 alpha-cholanoic acid	HMDB

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

IUPAC Name

(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

2393-59-1

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

InChI Identifier

InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1

InChI Key

DKPMWHFRUGMUKF-CRKPLTDNSA-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
6-hydroxysteroid
7-hydroxysteroid
7-alpha-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

bile acid (CHEBI:81298 )
C24 bile acids, alcohols, and derivatives (LMST04010067 )

Functional Ontology

Feces (PMID: 27275383)
Urine (PMID: 1112456)

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

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

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000415)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000415)

Source

Endogenous

Endogenous (HMDB: HMDB0000415)

Animal

Animal (HMDB: HMDB0000415)

Exogenous

Food

Food (HMDB: HMDB0000415)

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: HMDB0000415)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000415)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000415)

Lipid metabolism pathway (HMDB: HMDB0000415)

Cellular process

Cell signaling (HMDB: HMDB0000415)

Biochemical process

Lipid transport (HMDB: HMDB0000415)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.069 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.72	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-2.7	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	47.31 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

HMDB0000415

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022031

KNApSAcK ID

Not Available

Chemspider ID

4446941

KEGG Compound ID

C17726

BioCyc ID

CPD-16583

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5404

PubChem Compound

5283853

PDB ID

Not Available

ChEBI ID

81298

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Hsia, S. L.; Matschiner, John T.; Mahowald, Theodore A.; Elliott, Wm. H.; Doisy, E. A., Jr.; Thayer, Sidney A.; Doisy, Edward A. Bile acids. VII. Structure of acid I. Journal of Biological Chemistry (1958), 230 573-80.

Showing chemical card for 3a,6b,7b-Trihydroxy-5b-cholanoic acid (CFc000000314)

MOL for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

3D MOL for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

3D SDF for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

3D-SDF for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

PDB for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

3D PDB for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

SMILES for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

INCHI for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

Structure for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)

3D Structure for CFc000000314 (3a,6b,7b-Trihydroxy-5b-cholanoic acid)