CAS 2955-27-3 Ursocholic acid (HCID 122340)

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Basic information

CAS: 2955-27-3
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-UTLSPDKDSA-N
Molecular formula: C24H40O5
Average molar mass: 408.6 g/mol
Monoisotopic mass: 408.28757438

Overview

Ursocholic acid is a bile acid that is 5beta-cholan-24-oic acid bearing three hydroxy substituents at positions 3alpha, 7beta and 12alpha. It has a role as an EC 1.1.1.159 (7alpha-hydroxysteroid dehydrogenase) inhibitor and a human urinary metabolite. It is a C24-steroid, a trihydroxy-5beta-cholanic acid, a bile acid, a 7beta-hydroxy steroid, a 3alpha-hydroxy steroid and a 12alpha-hydroxy steroid. It is a conjugate acid of an ursocholate.

Names & identifiers

Preferred name: Ursocholic acid
IUPAC: (4R)-4-[(3R,5S,7S,8R,9S,10S,12S,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: 4-[(5S,7S,8S,10S,13R,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
Molecular formula: C24H40O5
Molecular weight: 408.58

Names & synonyms

ursocholic acid2955-27-37-Epicholic acid3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-oic acidMLP1T05RBXCHEBI:81240DTXSID3010187563alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acidRefChem:933866DTXCID601476787UrsocholateMFCD25563269

Show more names

3α,7β,12α-trihydroxy-5β-cholan-24-oic AcidBear bile acidUrsodiol Impurity D7β-Hydroxyisocholic AcidUrsocholic acid (Standard)Ursocholic acid, 10 mM in DMSO

(R)-4-((3R,5S,7S,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acidUrsodeoxycholic Acid EP Impurity D(4R)-4-[(3R,5S,7S,8R,9S,10S,12S,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 acid7beta-Hydroxyisocholic acidCholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7beta,12alpha)-7-epicholate3a,7b,12a-Trihydroxy-5b-cholanic acid3a,7b,12a-Trihydroxy-5b-cholan-24-oic acid

Properties

Computed structural properties

XLogP: 3.6
Topological polar surface area: 98 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 5
Rotatable bonds: 4
Heavy atoms: 29
Formal charge: 0
Complexity: 637

Experimental & physicochemical properties

LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]

Physical DescriptionSolid

Collision Cross Section · 2 items

205.1 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

203.3 Å² [M-H]-

Physicochemical properties

Melting point: 144 °C · 144 °C
Boiling point: 489.08 °C · 489.08°C (rough estimate)
Density: 1.0263 · 1.0263 (rough estimate)
refractive index: 1.54 · 1.5400 (estimate)
storage temp.: Refrigerator
solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
form: Solid
pka: 4.76 · 4.76±0.10(Predicted)
color: White to Pale Beige

Safety & regulation

Safety data

wgk: WGK 3
Storage Class: 11 - Combustible Solids

Chemistry & industry

Pharmacology

Tissue LocationsGall Bladder

Cellular LocationsExtracellular

Applications

UsesUrsocholic Acid (Ursodeoxycholic Acid EP Impurity D) is an Ursodeoxycholic Acid (U850000) impurity.

UsesUrsodeoxycholic acid (U850000) impurity.

Suppliers96 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Related reactions

2 records

New reaction record

HRID 1659376As productuspto-grants-1981_12

HRID 1659377As productuspto-grants-1981_12

Compound notes

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