3-[(1S,2S,6S)-1,3-dimethyl-2-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-6-(prop-1-en-2-yl)cyclohex-3-en-1-yl]propanoic acid

• ChemBase ID: 179747
• Molecular Formular: C24H28O5
• Molecular Mass: 396.47612
• Monoisotopic Mass: 396.193674
• SMILES: [C@@]1([C@H](C(=CC[C@H]1C(=C)C)C)COc1cc2oc(=O)ccc2cc1)(CCC(=O)O)C
• Canonical SMILES: OC(=O)CC[C@]1(C)[C@@H](COc2ccc3c(c2)oc(=O)cc3)C(=CC[C@H]1C(=C)C)C
• InChI: InChI=1S/C24H28O5/c1-15(2)19-9-5-16(3)20(24(19,4)12-11-22(25)26)14-28-18-8-6-17-7-10-23(27)29-21(17)13-18/h5-8,10,13,19-20H,1,9,11-12,14H2,2-4H3,(H,25,26)/t19-,20-,24-/m0/s1
• InChIKey: DRASTJFRZGDAQT-SKPFHBQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1S,2S,6S)-1,3-dimethyl-2-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-6-(prop-1-en-2-yl)cyclohex-3-en-1-yl]propanoic acid
• IUPAC Traditional name: 3-[(1S,2S,6S)-1,3-dimethyl-2-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-6-(prop-1-en-2-yl)cyclohex-3-en-1-yl]propanoic acid
• Synonyms: Karatavic acid

Database IDs

• CAS Number: 21800-49-7
• PubChem SID: 164235657
• PubChem CID: 10340705

CALCULATED PROPERTIES

• Acid pKa: 4.459478
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.371357
• LogD (pH = 7.4): 1.6068788
• Log P: 4.448334
• Molar Refractivity: 112.5222 cm^3
• Polarizability: 43.2965 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Biological Source: Constit. of roots of Ferula karatavica
• Application(s): Antiarteriosclerotic

REFERENCES

• Paknikar, S.K. et al., Chem. Ind. (London), 1978, 431, (struct)
• Nishizawa, M. et al., Tet. Lett., 1984, 25, 437, (synth)