7α,12α-Dihydroxy-5β-cholan-24-oic Acid - Moligand™, ≥98% , CAS No.566-17-6

CAS: 566-17-6 Cat. No.: D669675 Molecular Weight: 392.57

GRADE & PURITY Moligand™, ≥98%

Synonyms

(4R)-4-[(5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoicacid | Isodeoxycholicacid | isoDCA | 3-Deoxycholicacid

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Isodeoxycholic Acid is a bile acid that is formed via epimerization of deoxycholic acid by intestinal bacteria. It has a greater critical micelle concentration than DCA, indicating reduced detergent activity, and is less active than DCA in inhibiting growth in a panel of seven gut commensal bacteria species. Isodeoxycholic Acid(0.1%) inhibits spore germination induced by taurocholic acid in several C. difficile strains, as well as decreases the cytotoxicity of C. difficile culture supernatants to Vero cells. Plasma levels of isodeoxycholic acid are decreased in a rat model of high-fat diet-induced obesity compared with rats fed a normal diet.

Specifications

Synonyms

(4R)-4-[(5S, 7R, 8R, 9S, 10S, 12S, 13R, 14S, 17R)-7, 12-dihydroxy-10, 13-dimethyl-2, 3, 4, 5, 6, 7, 8, 9, 11, 12, 14, 15, 16, 17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoicacid | Isodeoxycholicacid | isoDCA | 3-Deoxycholicacid

Specifications & Purity

Moligand™, ≥98%

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™

Purity

≥98%

Product Properties

• ALogP: 5.3

Names and Identifiers

• Canonical Smiles: C[C@@]12[C@@]3([C@]([C@]4([C@](C)([C@@H](O)C3)[C@@]([C@@H](CCC(O)=O)C)(CC4)[H])[H])([C@H](O)C[C@@]1(CCCC2)[H])[H])[H]
• IUPAC Name: (4R)-4-[(5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-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
• InChIKey: ZHCAAZIHTDCFJX-QLEQUTGBSA-N
• INCHI: 1S/C24H40O4/c1-14(7-10-21(27)28)16-8-9-17-22-18(13-20(26)24(16,17)3)23(2)11-5-4-6-15(23)12-19(22)25/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CCCC4)C)O)O)C
• Molecular Weight: 392.57

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Bile acids, alcohols and derivatives
        • Level5 Hydroxy bile acids, alcohols and derivatives
          • Level6 Dihydroxy 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: Hydroxy bile acids, alcohols and derivatives
• Direct Parent: Dihydroxy bile acids, alcohols and derivatives
• Alternative Parents: 7-hydroxysteroids 12-hydroxysteroids Secondary alcohols Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Dihydroxy bile acid, alcohol, or derivatives - 12-hydroxysteroid - Hydroxysteroid - 7-hydroxysteroid - Cyclic alcohol - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Alcohol - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
• External Descriptors: C24 bile acids, alcohols, and derivatives

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

Chemical and Physical Properties

• Molecular Weight: 392.600 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 392.293 Da
• Monoisotopic Mass: 392.293 Da
• Topological Polar Surface Area: 77.800 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 605.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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