3alpha,7alpha,12beta-Trihydroxy-5beta-cholanic acid
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Basic information
- CAS
71883-64-2- Standard SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@@H](O)[C@]12C- InChIKey
BHQCQFFYRZLCQQ-KRHHAYMPSA-N- Molecular formula
- C24H40O5
- Average molar mass
- 408.6 g/mol
- Monoisotopic mass
- 408.28757437
Overview
3alpha,7alpha,12beta-trihydroxy-5beta-cholanic acid is a trihydroxy-5beta-cholanic acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3, 7 and 12 (the 3alpha,7alpha,12beta stereoisomer). It has a role as a human metabolite. It is a conjugate acid of a 3alpha,7alpha,12beta-trihydroxy-5beta-cholanate.
Names & identifiers
- Preferred name
- 3alpha,7alpha,12beta-Trihydroxy-5beta-cholanic acid
- IUPAC
- (4R)-4-[(3R,5S,7R,8R,9S,10S,12R,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
- English name
- (3a,5b,7a,12b)-3,7,12-trihydroxy-Cholan-24-oic acid
- Molecular formula
- C24H40O5
- Molecular weight
- 0
Names & synonyms
3alpha,7alpha,12beta-Trihydroxy-5beta-cholanic acid3alpha,7alpha,12beta-Trihydroxy-5beta-cholan-24-oic AcidCHEBI:36240RefChem:106888771883-64-2Lagocholic acid12beta-Hydroxyisocholic Acid12b-Hydroxyisocholic acid12|A-Hydroxyisocholic acid3a,7a,12b-Trihydroxy-5b-cholanoic acidUrsodeoxycholic Acid Impurity 46(4R)-4-[(3R,5S,7R,8R,9S,10S,12R,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Show more names
12β-Hydroxyisocholic AcidBHQCQFFYRZLCQQ-KRHHAYMPSA-N(3α,5β,7α,12β)-3,7,12-Trihydroxycholan-24-oic acid(3a,5b,7a,12b)-3,7,12-trihydroxy-Cholan-24-oic acidCholan-24-oic acid,3,7,12-trihydroxy-, (3a,5b,7a,12b)- (9CI)
(R)-4-((3R,5S,7R,8R,9S,10S,12R,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid3alpha,7alpha,12beta-Trihydroxy-5beta-cholanoic acid105227-32-512b-Hydroxyisocholateorb1979965SCHEMBL20714908DTXSID101226284Ursodeoxycholic Acid Impurity 113
Properties
Computed structural propertiesFilling in
- XLogP
- 3.6
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 637
Experimental & physicochemical properties
Chemical ClassesBile Acids -> Canonical Bile Acids
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
Physical DescriptionSolid
Collision Cross Section211.2 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]
Physicochemical properties
- solubility
- Methanol (Slightly)
- form
- Solid
- color
- White to Off-White
- Stability
- Hygroscopic
Chemistry & industry
Pharmacology
Tissue LocationsGall Bladder
Cellular LocationsExtracellular
Applications
Uses12b-Hydroxyisocholic Acid is a bile acid.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: 3alpha,7alpha,12beta-trihydroxy-5beta-cholanic acid is a trihydroxy-5beta-cholanic acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3, 7 and 12 (the 3alpha,7alpha,12beta stereoisomer). It has a role as a human metabolite. It is a conjugate acid of a 3alpha,7alpha,12beta-trihydroxy-5beta-cholanate.
Related reactions
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Compound notes
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