(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid
Basic information
- CAS
566-24-5- 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]3CC[C@]12C- InChIKey
RUDATBOHQWOJDD-JGFDLHJZSA-N- Molecular formula
- C24H40O4
- Average molar mass
- 392.6 g/mol
- Monoisotopic mass
- 392.29265975
Overview
3beta,7alpha-dihydroxy-5beta-cholan-24-oic acid is a dihydroxy-5beta-cholanic acid in which the two hydroxy groups are located at positions 3beta and 7alpha. The 3beta-hydroxy epimer of chenodeoxycholic acid. It has a role as a human metabolite. It is a dihydroxy-5beta-cholanic acid, a bile acid, a 3beta-hydroxy steroid and a 7alpha-hydroxy steroid. It is a conjugate acid of a 3beta,7alpha-dihydroxy-5beta-cholan-24-oate.
Names & identifiers
- Preferred name
- (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid
- IUPAC
- (4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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
- (4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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
- Molecular formula
- C24H40O4
- Molecular weight
- 392.57
Names & synonyms
566-24-5(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acidDTXSID001266009RefChem:1050192DTXCID701696661Isochenodeoxycholic acid3beta,7alpha-Dihydroxy-5beta-cholan-24-oic Acid(4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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(R)-4-((3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-DIHYDROXY-10,13-DIMETHYLHEXADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-17-YL)PENTANOIC ACID3beta,7alpha-Dihydroxy-5beta-cholanic acid3-epi-chenodeoxycholic acid3b,7a-dihydroxy-5b-cholanoic acid
Show more names
Ursodiol Impurity 13-beta-7-alfa-UrsodiolCholic Acid Related CompoundUrsodeoxycholic Acid Impurity KUrosodeoxycholic Acid Impurity KUrsodeoxycholic acid EP Impurity KUrosodeoxycholic Acid EP Impurity K
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 605
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 190 °C · >190°C (dec.)
- Boiling point
- 547.1 · 547.1±25.0 °C(Predicted)
- Density
- 1.128 · 1.128±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Acetonitrile (Slightly, Heated), Methanol (Slightly)
- pka
- 4.76 · 4.76±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311+H331
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301+H311+H331
- Precautionary statements
- P501-P261-P270-P271-P264-P280-P361+P364-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
Chemistry & industry
Pharmacology
Tissue LocationsGall Bladder
Cellular LocationsExtracellular
Applications
UsesIsochenodeoxycholic Acid is an epimer of common bile acid Chenodeoxycholic Acid (C291900), present in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate.
Additional notes
DefinitionChEBI: A dihydroxy-5beta-cholanic acid in which the two hydroxy groups are located at positions 3beta and 7alpha. The 3beta-hydroxy epimer of chenodeoxycholic acid.
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