Taurolithocholic Acid(TLCA) - Moligand™, ≥98% , CAS No.516-90-5

CAS: 516-90-5 Cat. No.: T767008 Peso molecular: 483.70

GRADE & PURITY Moligand™, ≥98%

Synonyms

Cholic acid Impurity 26 | Taurolithocholate | Lithocholyltaurine | taurolithocholic acid-3-sulphate

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Taurolithocholic acid (TLCA) is a taurine-conjugated form of the secondary bile acid lithocholic acidTLCA (75 μM) increases caspase-3 and -7 activity in Hep3B cells transfected with sodium taurocholate cotransporting peptide (NTCP), but not nontransfected Hep3B cells.   It has been used to induce cholestasis in ex vivo and in vivo animal models of hepatocellular cholestasis.  Serum levels of TLCA increase approximately 5-fold within two hours during an oral lipid tolerance test in humans.

Specifications

Sinónimos

Cholic acid Impurity 26 | Taurolithocholate | Lithocholyltaurine | taurolithocholic acid-3-sulphate

Especificaciones y pureza

Moligand™, ≥98%

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• IUPAC 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
• InChIKey: QBYUNVOYXHFVKC-GBURMNQMSA-N
• INCHI: 1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1
• Isómeros SMILES: C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
• CAS alternativo: 516-90-5
• Términos de entrada MeSH: Acid, Taurolithocholic;Lithocholate, Taurine;Lithocholyltaurine;Taurine Lithocholate;Taurolithocholate;Taurolithocholic Acid;Taurolithocholic Acid, Monosodium Salt
• Peso molecular: 483.70

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Steroids and steroid derivatives
      • Subclass Bile acids, alcohols and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Steroids and steroid derivatives
• Subclass: Bile acids, alcohols and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Taurinated bile acids and derivatives
• Alternative Parents: Monohydroxy bile acids, alcohols and derivatives 3-alpha-hydroxysteroids N-acyl amines Sulfonyls Organosulfonic acids Alkanesulfonic acids Secondary carboxylic acid amides Secondary alcohols Cyclic alcohols and derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Taurinated bile acid - Hydroxy bile acid, alcohol, or derivatives - Monohydroxy bile acid, alcohol, or derivatives - 3-hydroxysteroid - Hydroxysteroid - 3-alpha-hydroxysteroid - Fatty amide - N-acyl-amine - Fatty acyl - Sulfonyl - Organosulfonic acid - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Alkanesulfonic acid - Cyclic alcohol - Secondary carboxylic acid amide - Secondary alcohol - Carboxamide group - Carboxylic acid derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organosulfur compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Alcohol - Aliphatic homopolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.
• External Descriptors: Taurine conjugates

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Peso molecular: 483.700 g/mol
• XLogP3: 4.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 483.302 Da
• Monoisotopic Mass: 483.302 Da
• Topological Polar Surface Area: 112.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 825.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Chen Song, Hu Zongren, Tang Jianbang, Zhu Haipeng, Zheng Yuhua, Xiao Jiedong, Xu Youhua, Wang Yao, Luo Yi, Mo Xiaoying, Wu Yalan, Guo Jianwen, Zhang Yongliang, Luo Huanhuan.  (2024)  High temperature and humidity in the environment disrupt bile acid metabolism, the gut microbiome, and GLP-1 secretion in mice.  Communications Biology,  7  (1): (1-13).  [PMID:38632312] [10.1038/s42003-024-06158-w]