methyl (1S,2S,3R,4R,8R,9S,10R,13R,15R)-2-(acetyloxy)-13-(furan-3-yl)-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.03,8.011,15]hexadeca-5,11-diene-4-carboxylate

• ChemBase ID: 175016
• Molecular Formular: C30H36O9
• Molecular Mass: 540.60144
• Monoisotopic Mass: 540.23593273
• SMILES: C1=CC(=O)[C@]2([C@H]([C@@]1(C(=O)OC)C)[C@@H]([C@@H]1[C@]([C@@H]2CC(=O)OC)(C2=C([C@@H](C[C@H]2O1)c1ccoc1)C)C)OC(=O)C)C
• Canonical SMILES: COC(=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)OC)OC(=O)C
• InChI: InChI=1S/C30H36O9/c1-15-18(17-9-11-37-14-17)12-19-23(15)30(5)20(13-22(33)35-6)29(4)21(32)8-10-28(3,27(34)36-7)25(29)24(26(30)39-19)38-16(2)31/h8-11,14,18-20,24-26H,12-13H2,1-7H3/t18-,19-,20-,24+,25+,26-,28-,29+,30-/m1/s1
• InChIKey: NHOIBRJOQAYBJT-YKAYWHEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,2S,3R,4R,8R,9S,10R,13R,15R)-2-(acetyloxy)-13-(furan-3-yl)-9-(2-methoxy-2-oxoethyl)-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-carboxylate
• IUPAC Traditional name: methyl (1S,2S,3R,4R,8R,9S,10R,13R,15R)-2-(acetyloxy)-13-(furan-3-yl)-9-(2-methoxy-2-oxoethyl)-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-carboxylate
• Synonyms: (4α,5α,6α,7α,15β,17α)-6-(Acetyloxy)-7,15:21,23-Diepoxy-4,8-dimethyl-1-oxo- 18,24-dinor-11,12-secochola-2,13,20,22-tetraene-4,11-dicarboxylic Acid Dimethyl Ester; 5-(Acetyloxy)-2-(3-furanyl)-3,3a,4a,5,5a,6,9,9a,10,10a-decahydro-6-(methoxycarbonyl)-1,6,9a,10a-tetramethyl-9-oxo-2H-cyclopenta[b]naphtho[2,3-d]furan-10-acetic Acid Methyl Ester; Nimbin

Database IDs

• CAS Number: 5945-86-8
• PubChem SID: 164230926
• PubChem CID: 71750950

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.0665145
• LogD (pH = 7.4): 3.0665145
• Log P: 3.0665145
• Molar Refractivity: 139.2777 cm^3
• Polarizability: 54.829174 Å^3
• Polar Surface Area: 118.34 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 197-199°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N476280

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)