Taurolithocholic Acid(TLCA) - Moligand™, 100 µg/ml in methanol , CAS No.516-90-5

CAS: 516-90-5 Cat. No.: T614339 Molecular Weight: 483.70

GRADE & PURITY Moligand™, 100 µg/ml in methanol

Synonyms

Cholic acid Impurity 26

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

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

Synonyms

Cholic acid Impurity 26

Specifications & Purity

Moligand™, 100 µg/ml in methanol

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: 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
• Isomeric 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
• Alternate CAS: 516-90-5
• MeSH Entry Terms: Acid, Taurolithocholic;Lithocholate, Taurine;Lithocholyltaurine;Taurine Lithocholate;Taurolithocholate;Taurolithocholic Acid;Taurolithocholic Acid, Monosodium Salt
• Molecular Weight: 483.70

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: 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
• Description: 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

Associated Targets(Human)

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EPHA2 Tclin Ephrin type-A receptor 2 (3499 Activities)

Discover Target: EPHA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GPBAR1 Tchem G-protein coupled bile acid receptor 1 (1723 Activities)

Discover Target: GPBAR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)

Discover Target: ABCG2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

Discover Target: ABCC2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCB11 Tchem Bile salt export pump (2311 Activities)

Discover Target: ABCB11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO2B1 Tchem Solute carrier organic anion transporter family member 2B1 (580 Activities)

Discover Target: SLCO2B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

PLA2G1B Phospholipase A2 group 1B (227 Activities)

Discover Target: PLA2G1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcc1 Multidrug resistance-associated protein 1 (42 Activities)

Discover Target: Abcc1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcb1b P-glycoprotein 1 (174 Activities)

Discover Target: Abcb1b

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHO (4503 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc10a1 Bile acid transporter (65 Activities)

Discover Target: Slc10a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mdr1a Multidrug resistance protein 1a (106 Activities)

Discover Target: Mdr1a

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 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

References

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]