(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid

• ChemBase ID: 128095
• Molecular Formular: C24H40O3
• Molecular Mass: 376.5726
• Monoisotopic Mass: 376.29774514
• SMILES: O=C(O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2C[C@H](O)CC[C@]12C)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)C
• InChI: InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
• InChIKey: SMEROWZSTRWXGI-HVATVPOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• IUPAC Traditional name: lithocholic acid
• Synonyms: (3α,5β)-3-Hydroxycholan-24-oic Acid; 17β-(1-Methyl-3-carboxypropyl)etiocholan-3α-ol; 3-Hydroxycholan-24-oic Acid; 3α-Hydroxy-5β-cholan-24-oate; 3α-Hydroxy-5β-cholanoic Acid; 3α-Hydroxycholanic Acid; NSC 683770; Lithocholic acid; Lithocholate; Lithocolic acid; 3α-Hydroxy-5β-cholan-24-oic acid; 3α-Hydroxy-5β-cholanic acid; 5β-Cholan-24-oic acid-3α-ol; Lithocholic acid; 3α-羟基-5β-胆烷酸; 3α-羟基-5β-胆甾烷-24-酸; 5β-胆甾烷-24-酸-3α-醇; 石胆酸

Database IDs

• CAS Number: 434-13-9
• EC Number: 207-099-1
• MDL Number: MFCD00003682
• Beilstein Number: 3217757
• PubChem SID: 162222409; 24896429
• PubChem CID: 9903
• CHEBI ID: 16325
• CHEMBL: 1478
• Chemspider ID: 9519
• IUPHAR ligand ID: 611
• Wikipedia Title: Lithocholic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.7910433
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.2362366
• LogD (pH = 7.4): 2.4612968
• Log P: 5.0220704
• Molar Refractivity: 107.6813 cm^3
• Polarizability: 43.144962 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 183-188 °C; 183-188 °C(lit.); 183-189 °C; 189-191°C
• Optical Rotation: [α]20/D +35±1°, c = 1% in ethanol

Safety Information

• Storage Condition: Refrigerator
• RTECS: FZ2275000
• German water hazard class: 2
• Safety Statements: S22 S24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... POLA1(5422), TOP2A(7153)rat ... Polb(29240)

Product Information

• Purity: ≥97% (titration); ≥99.0% (TLC)
• Impurities: ~1% deoxycholic acid (TLC)
• Empirical Formula (Hill Notation): C24H40O3

DETAILS

Sigma Aldrich - L6250

Biochem/physiol Actions
Bile Acid
Packaging
10, 25 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. L6250.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 62620

Other Notes
One of the major fecal bile acids of humans.; Causes calcium release from the endoplasmic reticulum in rat liver cells1

Toronto Research Chemicals - L469180

A cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

REFERENCES

• Brindle, J., et al.: Nat. Med., 12, 1439 (2002)
• Lindon, J., et al.: Biomarkers, 9, 1 (2002)
• Holmes, E., et al.: Cell, 134, 714 (2002)