(1S,2R,3R,4R,8R,9S,10R,13R,15R)-9-(carboxymethyl)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.03,8.011,15]hexadeca-5,11-diene-4-carboxylic acid

• ChemBase ID: 175015
• Molecular Formular: C26H30O8
• Molecular Mass: 470.5116
• Monoisotopic Mass: 470.19406792
• SMILES: C1=CC(=O)[C@]2([C@H]([C@@]1(C(=O)O)C)[C@H]([C@@H]1[C@]([C@@H]2CC(=O)O)(C2=C([C@@H](C[C@H]2O1)c1ccoc1)C)C)O)C
• Canonical SMILES: OC(=O)C[C@H]1[C@@]2(C)[C@H](O[C@H]3C2=C(C)[C@@H](C3)c2cocc2)[C@@H]([C@@H]2[C@]1(C)C(=O)C=C[C@@]2(C)C(=O)O)O
• InChI: InChI=1S/C26H30O8/c1-12-14(13-6-8-33-11-13)9-15-19(12)26(4)16(10-18(28)29)25(3)17(27)5-7-24(2,23(31)32)21(25)20(30)22(26)34-15/h5-8,11,14-16,20-22,30H,9-10H2,1-4H3,(H,28,29)(H,31,32)/t14-,15-,16-,20-,21+,22-,24-,25+,26-/m1/s1
• InChIKey: HJTQADUXZXDMJC-RSARTRMLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3R,4R,8R,9S,10R,13R,15R)-9-(carboxymethyl)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^3,^8.0^1^1,^1^5]hexadeca-5,11-diene-4-carboxylic acid
• IUPAC Traditional name: (1S,2R,3R,4R,8R,9S,10R,13R,15R)-9-(carboxymethyl)-13-(furan-3-yl)-2-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^3,^8.0^1^1,^1^5]hexadeca-5,11-diene-4-carboxylic acid
• Synonyms: Nimbic Acid

Database IDs

• PubChem SID: 164230925
• PubChem CID: 71750949

CALCULATED PROPERTIES

• Acid pKa: 3.939026
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.030550482
• LogD (pH = 7.4): -3.467766
• Log P: 2.333601
• Molar Refractivity: 120.588 cm^3
• Polarizability: 46.830223 Å^3
• Polar Surface Area: 134.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - N476250

Nimbin (N476280) derivative. A new limonoid from Arisaema decipiens, a traditional antitumor herb.

REFERENCES

• Cohen, E., et al.: Life Sci., 58, 1075 (1996)
• Roy, A., et al.: Biol. Pharm. Bull., 29, 191 (1996)