Ursocholic acid

HCID 122340CAS 2955-27-3
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Grundinformationen

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
Summenformel
C24H40O5
Durchschnittliche Molmasse
408,6 g/mol
Monoisotopische Masse
408,28757438

Überblick

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.

Namen und Bezeichner

Bevorzugter 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
Englischer 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
Summenformel
C24H40O5
Molmasse
408.58

Namen und Synonyme

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

Datenbank-Bezeichner

CAS
2955-27-3
PubChem CID
122340
DTXSID
DTXSID301018756
ChEMBL
CHEMBL1254416
ChEBI
CHEBI:81240
UNII
MLP1T05RBX
Nikkaji
J363.683F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,6
Polarare Oberfläche (TPSA)
98 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
29

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
Physical DescriptionSolid
Collision Cross Section · 2 Einträge

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

203.3 Ų [M-H]-

Physikochemische Eigenschaften

Schmelzpunkt
144 °C · 144 °C
Siedepunkt
489.08 °C · 489.08°C (rough estimate)
Dichte
1.0263 · 1.0263 (rough estimate)
Brechungsindex
1.54 · 1.5400 (estimate)
storage temp.
Refrigerator
Löslichkeit
DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk
WGK 3
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsGall Bladder
Cellular LocationsExtracellular

Anwendungen

VerwendenUrsodeoxycholic acid (U850000) impurity.

Anbieter50 Anbieter

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]

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