3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acid
Grundinformationen
- CAS
338976-79-7- Standard-SMILES
CC(CCC[C@@H](C)[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)C(=O)O- InChIKey
CNWPIIOQKZNXBB-VCVMUKOKSA-N- Summenformel
- C27H46O5
- Durchschnittliche Molmasse
- 450,7 g/mol
Überblick
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid is a steroid acid that is 5beta-cholestan-26-oic acid which is substituted by hydroxy groups as the 3alpha, 7alpha, and 12alpha positions. It has a role as a human metabolite. It is a hydroxy monocarboxylic acid, a 3alpha-hydroxy steroid, a 7alpha-hydroxy steroid, a 12alpha-hydroxy steroid and a steroid acid. It is a conjugate acid of a 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate(1-). It derives from a hydride of a 5beta-cholestane.
Namen und Bezeichner
- Bevorzugter Name
- 3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acid
- IUPAC
- (6R)-2-methyl-6-[(3R,5S,7R,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]heptanoic acid
- Englischer Name
- 3α,7α,12α-Trihydroxycoprostanic Acid-d3
- Summenformel
- C27H46O5
- Molmasse
- 450.66
Namen und Synonyme
Coprocholic acid3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholestan-26-oic acid(6R)-2-methyl-6-[(3R,5S,7R,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]heptanoic acidCHEBI:18402(6R)-2-methyl-6-((3R,5S,7R,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)heptanoic acidRefChem:1068885Trihydroxycholestanoic acid547-98-8trihydroxycoprostanic acid3,7,12-trihydroxycholestan-26-oic acid(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-oic acid3?,7?,12?-Trihydroxycoprostanic Acid
Weitere Namen anzeigen
-TrihydroxycoprostanicAcid-d33a,7a,12a-Trihydroxycoprostanic Acid D33α,7α,12α-Trihydroxycoprostanic Acid-d3D3-3α,7α,12α-Trihydroxycoprostanic Acid3Alpha,7Alpha,12Alpha-Trihydroxycoprostanic Acid-d3
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,2
- Polarare Oberfläche (TPSA)
- 98 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 32
- Formalladung
- 0
- Komplexität
- 696
Experimentelle und physikochemische Eigenschaften
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C27 bile acids, alcohols, and derivatives [ST0403]
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 118 · 118 - 121°C
- storage temp.
- Refrigerator
- Löslichkeit
- DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsGall Bladder
Cellular LocationsExtracellular
Metabolite Pathways27-Hydroxylase Deficiency
Anwendungen
Verwenden3α,7α,12α-Trihydroxycoprostanic Acid-d3 is a labelled analogue of 3α,7α,12α-Trihydroxycoprostanic Acid (T795155), a precursor of Cholic Acid (C432600), it undergoes side chain oxidation during the synthesis of bile acids. It was found that Zellweger’s syndrome patients have abnormal mitochondrial structure, the organelle that is responsible for the side chain oxidation, and as a consequence, excess amounts of 3α,7α,12α-Trihydroxycoprostanic Acid.
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