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

• ChemBase ID: 175014
• Molecular Formular: C29H34O8
• Molecular Mass: 510.57546
• Monoisotopic Mass: 510.22536805
• SMILES: C1=CC(=O)[C@]2([C@H]([C@@]1(C=O)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(=O)C
• InChI: InChI=1S/C29H34O8/c1-15-18(17-8-10-35-13-17)11-19-23(15)29(5)20(12-22(33)34-6)28(4)21(32)7-9-27(3,14-30)25(28)24(26(29)37-19)36-16(2)31/h7-10,13-14,18-20,24-26H,11-12H2,1-6H3/t18-,19-,20-,24-,25+,26-,27+,28+,29-/m1/s1
• InChIKey: KTZMJZLZKQMODA-AGKCECBESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-[(1S,2R,3S,4R,8R,9S,10R,13R,15R)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^3,^8.0^1^1,^1^5]hexadeca-5,11-dien-9-yl]acetate
• IUPAC Traditional name: methyl 2-[(1S,2R,3S,4R,8R,9S,10R,13R,15R)-2-(acetyloxy)-4-formyl-13-(furan-3-yl)-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^3,^8.0^1^1,^1^5]hexadeca-5,11-dien-9-yl]acetate
• Synonyms: (2R,3aR,4aS,5R,5aS,6R,9aR,10S,10aR)-5-(Acetyloxy)-6-formyl-2-(3-furanyl)-3,3a,4a,5,5a,6,9,9a,10,10a-decahydro-1,6,9a,10a-tetramethyl-9-oxo-2H-cyclopenta[b]naphtho[2,3-d]furan-10-acetic Acid Methyl Ester; (4α,5α,6α,7α,15β,17α)-6-(Acetyloxy)-7,15:21,23-diepoxy-4-formyl-4,8-dimethyl-1-oxo-24-nor-12,13-secochola-2,13,20,22-tetraen-12-oic Acid Methyl Ester; Nimbanal

Database IDs

• CAS Number: 120462-51-3
• PubChem SID: 164230924
• PubChem CID: 14194023

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.7620041
• LogD (pH = 7.4): 2.7620041
• Log P: 2.7620041
• Molar Refractivity: 133.5832 cm^3
• Polarizability: 52.270485 Å^3
• Polar Surface Area: 109.11 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - N476210

Nimbin (N476280) derivative.

REFERENCES

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