Taurolithocholic Acid

HCID 439763CAS 516-90-5

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Grundinformationen

Standard-SMILES: C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey: QBYUNVOYXHFVKC-GBURMNQMSA-N
Summenformel: C26H45NO5S
Durchschnittliche Molmasse: 483,7 g/mol
Monoisotopische Masse: 483,30184454

Überblick

Taurolithocholic acid is the bile acid taurine conjugate of lithocholic acid. It has a role as a human metabolite. It is a bile acid taurine conjugate and a monocarboxylic acid amide. It is functionally related to a lithocholic acid. It is a conjugate acid of a taurolithocholate.

Namen und Bezeichner

Bevorzugter Name: Taurolithocholic Acid
IUPAC: 2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
Englischer Name: 2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
Summenformel: C26H45NO5S
Molmasse: 483.7

Namen und Synonyme

TAUROLITHOCHOLIC ACID516-90-5LithocholyltaurineDTXSID209659252-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acidCHEBI:36259N-(3alpha-hydroxy-5beta-cholan-24-oyl)-taurineAcid, TaurolithocholicLithocholate, TaurineEthanesulfonic acid, 2-(((3alpha,5beta)-3-hydroxy-24-oxocholan-24-yl)amino)-2-(((4R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)pentanoyl)amino)ethanesulfonic acidRefChem:389301

Weitere Namen anzeigen

Apigenine Impurity 6Cholic acid Impurity 72Taurolithocholic Acid D8Taurodeoxycholic Acid Impurity 3Taurolithocholic Acid MaxSpec? StandardN-(3α-Hydroxy-24-oxo-5β-cholan-24-yl)taurine5β-CHOLANIC ACID-3α-OL N-(2-SULPHOETHYL)-AMIDE

DTXCID601393579TaurolithocholateTLCAtaurolithocholic acid-3-sulphate2-((R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)ethane-1-sulfonic acidCHEMBL408701Lithocholic acid taurine conjugateTAUROLITHOCHOLIC ACID(TLCA)

Datenbank-Bezeichner

CAS: 516-90-5
PubChem CID: 439763
DTXSID: DTXSID20965925
ChEMBL: CHEMBL408701
ChEBI: CHEBI:36259
Nikkaji: J337.752K

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 4,9
Polarare Oberfläche (TPSA): 112 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 7
Schwere Atome: 33
Formalladung: 0
Komplexität: 825

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBile Acids -> Quant Bile Acids

LipidsLipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Taurine conjugates [ST0504]

Melting Point212 - 213 °C

Physical DescriptionSolid

Collision Cross Section · 5 Einträge

212.4 Å² [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]

204.62 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

213.1 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

206.4 Å² [M-H]- [CCS Type: DT; Method: single field calibrated]

206.5 Å² [M-H]-

Physikochemische Eigenschaften

Schmelzpunkt: 212 · 212-213 °C
Dichte: 1.0476 · 1.0476 (rough estimate)
Brechungsindex: 1.565 · 1.5650 (estimate)
storage temp.: -20 °C · -20°C
Aggregatzustand: powder
pka: 1.42 · 1.42±0.50(Predicted)
Farbe: Colorless to light yellow

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic).

Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.

Tissue LocationsGall Bladder

Cellular LocationsExtracellular

Metabolite Pathways27-Hydroxylase Deficiency