Hyocholic Acid
Basic information
- CAS
547-75-1- Standard SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
DKPMWHFRUGMUKF-KWXDGCAGSA-N- Molecular formula
- C24H40O5
- Average molar mass
- 408.6 g/mol
- Monoisotopic mass
- 408.28757437
Overview
Hyocholic acid is a trihydroxy-5beta-cholanic acid in which the three hydroxy substituents are located at the 3alpha-, 6alpha- and 7alpha-positions. It has a role as a mouse metabolite, a human urinary metabolite and a rat metabolite. It is a C24-steroid, a member of muricholic acids, a 7alpha-hydroxy steroid and a 6alpha-hydroxy steroid. It is a conjugate acid of a hyocholate.
Names & identifiers
- Preferred name
- Hyocholic Acid
- IUPAC
- (4R)-4-[(3R,5R,6R,7S,8S,9S,10R,13R,14S,17R)-3,6,7-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
- Hyocholic acid
- Molecular formula
- C24H40O5
- Molecular weight
- 408.57
Names & synonyms
Hyocholic acid547-75-1gamma-Muricholic acidIocholic acid(4R)-4-[(3R,5R,6R,7S,8S,9S,10R,13R,14S,17R)-3,6,7-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 acid2H5H0Q47FL6alpha-Hydroxychenodeoxycholic acidCHEBI:81244DTXSID20862167Cholan-24-oic acid, 3,6,7-trihydroxy-, (3alpha,5beta,6alpha,7alpha)-(4R)-4-((3R,5R,6R,7S,8S,9S,10R,13R,14S,17R)-3,6,7-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 acidRefChem:147344
Show more names
Hyocholic acid (HCA)GAMMA MURICHOLIC6B13u0003B16u0003B17u0003B1-trihydroxy-5B2
DTXCID501475574208-935-83a,6a,7a-Trihydroxy-5b-cholanic acid3alpha,6alpha,7alpha-Trihydroxy-5beta-cholan-24-oic acid5b-Cholanic acid-3a,6a,7a-triol(R)-4-((3R,5R,6R,7S,8S,9S,10R,13R,14S,17R)-3,6,7-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acidalpha-Hyocholic acidCholan-24-oic acid, 3,6,7-trihydroxy-, (3.alpha.,5.beta.,6.alpha.,7.alpha.)-
Properties
Computed structural properties
- XLogP
- 3.9
- 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]
Collision Cross Section
202.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: Bile Acids]
206 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
197 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated]
204.2 Ų [M-H]-
Physicochemical properties
- Melting point
- 162 °C · 162 °C
- Boiling point
- 565.7 · 565.7±40.0 °C(Predicted)
- Density
- 1.184 · 1.184±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Ethanol (Slightly), Methanol (Slightly, Heated)
- form
- Solid
- pka
- 4.76 · 4.76±0.10(Predicted)
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
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHyocholic acid has known human metabolites that include hyocholic acid 24-O-glucuronide and hyocholic acid 6-O-glucuronide.
Applications
Uses3α,6α,7α-Trihydroxy-5β-cholanic Acid is one of the bile acids categorizes under muricholic acid, a group of bile acids found in human urine due to its additional hydroxyl groups. The synthesis of 3α,6α,7α-Trihydroxy-5β-cholanic Acid was shown to be promoted due to overexpression of cholesterol 7α-hydroxylase enzyme.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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