2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

• ChemBase ID: 1883
• Molecular Formular: C26H43NO5
• Molecular Mass: 449.62332
• Monoisotopic Mass: 449.31412348
• SMILES: C1C[C@H](C[C@H]2C[C@H]([C@@H]3[C@@H]([C@@]12C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CCC(=O)NCC(=O)O)C)C)O)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCC(=O)O)C)C)O)C
• InChI: InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-/m1/s1
• InChIKey: GHCZAUBVMUEKKP-GYPHWSFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid; 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetic acid
• IUPAC Traditional name: glycochenodeoxycholic acid
• Synonyms: Glycochenodeoxycholic Acid

Database IDs

• CAS Number: 640-79-9
• PubChem SID: 46506300; 160965338
• PubChem CID: 12544
• Wikipedia Title: Glycochenodeoxycholic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7733076
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.8800022
• LogD (pH = 7.4): -0.66643345
• Log P: 2.6080222
• Molar Refractivity: 122.0773 cm^3
• Polarizability: 48.680336 Å^3
• Polar Surface Area: 106.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.4
• LOG S: -4.75
• Solubility (Water): 7.93e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.00315 mg/mL at 20 oC [RODA,A et al. (1990)]
• Hydrophobicity(logP): 2.12 [RODA,A ET AL. (1990)]

DETAILS

DrugBank - DB02123

• Drug Groups: experimental
• Description: A bile salt formed in the liver from chenodeoxycholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic. [PubChem]