alpha-Muricholic acid
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Basic information
- CAS
2393-58-0- 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-GDYCBZMLSA-N- Molecular formula
- C24H40O5
- Average molar mass
- 408.6 g/mol
- Monoisotopic mass
- 408.28757437
Overview
Alpha-muricholic acid is a member of the class of muricholic acids in which the hydroxy groups at positions 6 and 7 have beta- and alpha- configuration respectively. It is a member of muricholic acids, a 7alpha-hydroxy steroid and a 6beta-hydroxy steroid. It is a conjugate acid of an alpha-muricholate.
Names & identifiers
- Preferred name
- alpha-Muricholic acid
- IUPAC
- (4R)-4-[(3R,5R,6S,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
- α-Muricholic Acid
- Molecular formula
- C24H40O5
- Molecular weight
- 408.58
Names & synonyms
alpha-Muricholic acid2393-58-03alpha,6beta,7alpha-Trihydroxy-5beta-cholan-24-oic AcidCHEBI:81243DTXSID101316249RefChem:915560DTXCID601746112a-Muricholic acidalpha-MCA5beta-Cholanic acid-3alpha,6beta,7alpha-triol(4R)-4-[(3R,5R,6S,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(3a,5b,6b,7a)-3,6,7-trihydroxy-Cholan-24-oic acid
Show more names
alpha-Muricholateα-Muricholic Acidalfa-Muricholic AcidD5-α-Muricholic Acid2H5]-α-Muricholic AcidDKPMWHFRUGMUKF-GDYCBZMLSA-Nα-Muricholic acid (Standard)Hyodeoxycholic acid Impurity 13
Ursodeoxycholic acid impurity 293a,6b,7a-trihydroxy-5b-Cholanic acidCholan-24-oic acid, 3,6,7-trihydroxy-, (3alpha,5beta,6beta,7alpha)-(R)-4-((3R,5R,6S,7S,8S,9S,10R,13R,14S,17R)-3,6,7-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acida-MuricholateST 24:1;O5| cent-Muricholic acidorb1706041
Properties
Computed structural propertiesFilling in
- 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]
Melting Point199 - 200 °C
Physical DescriptionSolid
Collision Cross Section
211.9 Ų [M+NH4]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]
201 Ų [M+Na-H+Cl]- [CCS Type: DT; Method: single field calibrated]
205.6 Ų [M-H]-
Physicochemical properties
- Melting point
- 200 · 200-202 °C
- Boiling point
- 565.7 · 565.7±40.0 °C(Predicted)
- Density
- 1.184 · 1.184±0.06 g/cm3(Predicted)
- storage temp.
- Refrigerator
- solubility
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
Tissue LocationsGall Bladder
Cellular LocationsExtracellular
Applications
Descriptionα-Muricholic acid is a murine-specific primary bile acid. Dietary administration of soybean protein decreases fecal levels of α-muricholic acid in mice with high-fat diet-induced obesity which correlates with increases in fecal Clostridium cluster XIVa, a major producer of secondary bile acids. Plasma, liver, and muscle levels of α-muricholic acid are increased in mice switched from a high-fat to low-fat diet.
Usesα-Muricholic Acid is an bile acid found in urine. Studies have linked α-Muricholic in the understanding of the complex signaling pathways of hepatic lipid abnormalities with type 2 diabetes and a treatment target for this condition.
Additional notes
DefinitionChEBI: Alpha-muricholic acid is a member of the class of muricholic acids in which the hydroxy groups at positions 6 and 7 have beta- and alpha- configuration respectively. It is a member of muricholic acids, a 6beta-hydroxy steroid and a 7alpha-hydroxy steroid. It is a conjugate acid of an alpha-muricholate.
Related reactions
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Compound notes
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