(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid

• ChemBase ID: 2385
• Molecular Formular: C24H40O5
• Molecular Mass: 408.5714
• Monoisotopic Mass: 408.28757438
• SMILES: C1C[C@@H](O)C[C@H]2C[C@@H](O)[C@@H]3[C@@H]([C@@]12C)C[C@H](O)[C@]1([C@H]3CC[C@@H]1[C@H](C)CCC(=O)O)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)O)C
• InChI: InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
• InChIKey: BHQCQFFYRZLCQQ-OELDTZBJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid; (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanoic acid; (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
• IUPAC Traditional name: cholic acid
• Synonyms: 3α,7α,12α-Trihydroxy-5β-cholanic acid; (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid; Cholic acid; 3α,7α,12α-Trihydroxy-5 β-cholan-24-ic acid; Cholanic acid; Cholic Acid; 3α,7α,12α-trihydroxy-5β-cholanoic acid; 3α,7α,12α-三羟基-5β-胆烷酸; 胆甾烷酸; 胆酸

Database IDs

• CAS Number: 81-25-4
• EC Number: 201-337-8
• MDL Number: MFCD00003672
• Beilstein Number: 2822009
• PubChem SID: 24892356; 160965836; 46507063
• PubChem CID: 221493
• CHEBI ID: 16359
• ATC CODE: A05AA03
• CHEMBL: 205596
• Chemspider ID: 192176
• DrugBank ID: DB02659
• Unique Ingredient Identifier: G1JO7801AE
• Wikipedia Title: Cholic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.4750123
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.4196734
• LogD (pH = 7.4): -0.346591
• Log P: 2.4824944
• Molar Refractivity: 110.7893 cm^3
• Polarizability: 44.403893 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.26
• LOG S: -3.74
• Solubility (Water): 7.38e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.175 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; methanol: soluble0.1 g/mL, clear
• Melting Point: 197-201 °C; 198-200°C; 200-201 °C; 200-201 °C(lit.)
• Optical Rotation: [α]20/D +36±2°, c = 0.6% in ethanol
• Hydrophobicity(logP): 2.02 [RODA,A ET AL. (1990)]
• Critical Micelle Concentration: 9-15
• Aggregation Number of Micelle: 2-3
• Hydrophilic Lipophilic Balance: 18

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: FZ9350000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: ≥98%; ≥99.0% (T); 98%
• Description: anionic
• Biological Source: from ox or sheep bile
• Mol. Weight: average mol wt 900-1300
• Empirical Formula (Hill Notation): C24H40O5

DETAILS

MP Biomedicals - 02101383

From Ox or Sheep Bile

DrugBank - DB02659

• Drug Groups: experimental
• Description: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. [PubChem]

Sigma Aldrich - C1129

Application
用于提取膜蛋白的非变性离子洗涤剂。
Biochem/physiol Actions
胆汁酸
包装
1 kg in poly bottle
25, 100, 500 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. C1129.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 27010

Application
Non-denaturing ionic detergent used for extraction of membrane proteins.
Biochem/physiol Actions
Bile Acid
Other Notes
For the solubilization of membrane-bound proteins in their native state1; Component for the preparation of liposomes2