Methyl cholate - ≥97% , CAS No.1448-36-8

CAS: 1448-36-8 Cat. No.: M102126 Molecular Weight: 422.61 EC Number: 215-903-7

GRADE & PURITY ≥97%

Synonyms

CHEBI:177012 | EINECS 215-903-7 | Cholan-24-oic acid, 3,7,12-trihydroxy-, methyl ester, (3alpha,5beta,7alpha,12alpha)- | 4M-731 | Cholic acid, methyl ester | methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

CHEBI:177012 | EINECS 215-903-7 | Cholan-24-oic acid, 3, 7, 12-trihydroxy-, methyl ester, (3alpha, 5beta, 7alpha, 12alpha)- | 4M-731 | Cholic acid, methyl ester | methyl (4R)-4-[(3R, 5S, 7R, 8R, 9S, 10S, 12S, 13R, 14S, 17R)-3, 7, 12-trihydroxy-10, 13-dimethyl-2, 3, 4, 5, 6, 7,

Specifications & Purity

≥97%

Storage

Room temperature

Shipped In

Normal

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504765792
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765792
• Canonical Smiles: CC(CCC(=O)OC)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
• IUPAC Name: methyl (4R)-4-[(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]pentanoate
• InChIKey: DLYVTEULDNMQAR-SRNOMOOLSA-N
• INCHI: 1S/C25H42O5/c1-14(5-8-22(29)30-4)17-6-7-18-23-19(13-21(28)25(17,18)3)24(2)10-9-16(26)11-15(24)12-20(23)27/h14-21,23,26-28H,5-13H2,1-4H3/t14-,15+,16-,17-,18+,19+,20-,21+,23+,24+,25-/m1/s1
• Isomeric SMILES: C[C@H](CCC(=O)OC)[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(CC[C@H](C4)O)C)O)O)C
• Molecular Weight: 422.61
• Reaxy-Rn: 2822409
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2822409&ln=

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 Trihydroxy 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: Trihydroxy bile acids, alcohols and derivatives
• Alternative Parents: 7-hydroxysteroids 3-alpha-hydroxysteroids 12-hydroxysteroids Fatty acid methyl esters Methyl esters Secondary alcohols Cyclic alcohols and derivatives Polyols Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Trihydroxy bile acid, alcohol, or derivatives - 3-hydroxysteroid - 7-hydroxysteroid - 3-alpha-hydroxysteroid - 12-hydroxysteroid - Hydroxysteroid - Fatty acid ester - Fatty acid methyl ester - Fatty acyl - Cyclic alcohol - Methyl ester - Carboxylic acid ester - Secondary alcohol - Polyol - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Organooxygen compound - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
• External Descriptors: Not available

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)

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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

Discover Target: SLCO1B1

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

Discover Target: SLCO1B3

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Associated Targets(non-human)

Cruzipain (33337 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Aspergillus fumigatus (16427 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Candida parapsilosis (8521 Activities)

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Sporothrix schenckii (1580 Activities)

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Trichophyton mentagrophytes (4846 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in warm methanol (1/20-clear), DMSO, and chloroform. Insoluble in water; Soluble in medium polarity organic solvents;Solubility in hot Methanol very faint turbidity
• Specific Rotation[α]: +32.0 to +37.0 deg(C=2, EtOH)
• Melt Point(°C): 153-157°C
• Molecular Weight: 422.600 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 422.303 Da
• Monoisotopic Mass: 422.303 Da
• Topological Polar Surface Area: 87.000 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 651.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• 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. Dan Ma, Hai Zhang, An-ru Liao, Qian-rong Peng, Min Yang.  (2025)  A bifunctional drug delivery system with targeting and glutathione-responsivity amphiphiles for effective tumor therapy.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2025.107041]