4-{[(4S)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentyl]oxy}-4-oxobutanoic acid

• ChemBase ID: 172088
• Molecular Formular: C28H44O7
• Molecular Mass: 492.64476
• Monoisotopic Mass: 492.30870375
• SMILES: C1C(=O)C[C@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@H](CCCOC(=O)CCC(=O)O)C)C)C
• Canonical SMILES: OC(=O)CCC(=O)OCCC[C@@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@H]2[C@H](O)C[C@@H]2[C@]1(C)CCC(=O)C2)C
• InChI: InChI=1S/C28H44O7/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/h16-17,19-23,26,30-31H,4-15H2,1-3H3,(H,32,33)/t16-,17+,19+,20-,21-,22+,23-,26-,27-,28+/m0/s1
• InChIKey: HUZHTVOPEPKVLN-GICMUOHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(4S)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentyl]oxy}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{[(4S)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentyl]oxy}-4-oxobutanoic acid
• Synonyms: (5α,7α,12α)-24-(3-Carboxy-1-oxopropoxy)-7,12-dihydroxy-cholan-3-one; 3-Keto Petromyzonol 24-Hemisuccinate

Database IDs

• CAS Number: 550298-38-9
• PubChem SID: 164227998
• PubChem CID: 71749688

CALCULATED PROPERTIES

• Acid pKa: 4.1031084
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.428748
• LogD (pH = 7.4): -0.2574502
• Log P: 2.8395467
• Molar Refractivity: 130.0693 cm^3
• Polarizability: 52.02217 Å^3
• Polar Surface Area: 121.13 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone
• Apperance: White Crystalline Powder
• Melting Point: 170-172°C

DETAILS

Toronto Research Chemicals - K200050

A succinic acid derivative of 3-keto petromyzonol, useful for conjugation.

REFERENCES

• Haslewood, G., et al.: Biochem. J. 114, 179 (1969)
• Sorensen, P.W., et al.: J. Gen. Physiol., 105, 569 (1995)