4-oxo-4-{[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentyl]oxy}butanoic acid

• ChemBase ID: 176413
• Molecular Formular: C28H46O7
• Molecular Mass: 494.66064
• Monoisotopic Mass: 494.32435381
• SMILES: C1[C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)(C(CC2)[C@@H](CCCOC(=O)CCC(=O)O)C)C)C)O
• 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]1CCC2[C@@H](CCCOC(=O)CCC(=O)O)C)C)O)C
• InChI: InChI=1S/C28H46O7/c1-16(5-4-12-35-25(34)9-8-24(32)33)19-6-7-20-26-21(15-23(31)28(19,20)3)27(2)11-10-18(29)13-17(27)14-22(26)30/h16-23,26,29-31H,4-15H2,1-3H3,(H,32,33)/t16-,17-,18-,19?,20+,21+,22-,23+,26+,27+,28-/m1/s1
• InChIKey: YVLYOODHWSNQSW-AWGSNEDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-oxo-4-{[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentyl]oxy}butanoic acid
• IUPAC Traditional name: 4-oxo-4-{[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentyl]oxy}butanoic acid
• Synonyms: (3α,7α,12α)-24-(3-Carboxy-1-oxopropoxy)-3,7,12-trihydroxycholan; Petromyzonol 24-Hemisuccinate

Database IDs

• PubChem SID: 164232323
• PubChem CID: 71751547

CALCULATED PROPERTIES

• Acid pKa: 4.1031094
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.221247
• LogD (pH = 7.4): -0.464951
• Log P: 2.6320457
• Molar Refractivity: 131.0974 cm^3
• Polarizability: 52.564568 Å^3
• Polar Surface Area: 124.29 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Crystalline Powder
• Melting Point: 187-189°C

DETAILS

Toronto Research Chemicals - P293515

Petromyzonol (P293500) derivative.

REFERENCES

• Haslewood, G, et al.: Biochem. J., 114, 179 (1969)
• Sorensen, P.W., et al.: J. Gen. Physiol., 105, 569 (1969)