Ursocholic acid
Grundinformationen
- 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- 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
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
- Formalladung
- 0
- Komplexität
- 637
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
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)
- Aggregatzustand
- Solid
- pka
- 4.76 · 4.76±0.10(Predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsGall Bladder
Cellular LocationsExtracellular
Anwendungen
VerwendenUrsodeoxycholic acid (U850000) impurity.
Zugehörige Reaktionen
2
Notizen zur Verbindung
Wird geladen…