methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadeca-7,13-dien-10-yl]acetate

• ChemBase ID: 175017
• Molecular Formular: C27H30O7
• Molecular Mass: 466.5229
• Monoisotopic Mass: 466.1991533
• SMILES: C12C(C(C3(C4C1OC(=O)C4(C=CC3=O)C)C)CC(=O)OC)(C1=C(C(CC1O2)c1ccoc1)C)C
• Canonical SMILES: COC(=O)CC1C2(C)C(OC3C2=C(C)C(C3)c2cocc2)C2C3C1(C)C(=O)C=CC3(C)C(=O)O2
• InChI: InChI=1S/C27H30O7/c1-13-15(14-7-9-32-12-14)10-16-20(13)27(4)17(11-19(29)31-5)26(3)18(28)6-8-25(2)22(26)21(23(27)33-16)34-24(25)30/h6-9,12,15-17,21-23H,10-11H2,1-5H3
• InChIKey: JZIQWNPPBKFOPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0^2,^9.0^4,^8.0^1^5,^1^8]octadeca-7,13-dien-10-yl]acetate
• IUPAC Traditional name: methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0^2,^9.0^4,^8.0^1^5,^1^8]octadeca-7,13-dien-10-yl]acetate
• Synonyms: (4α,5α,6α,7α,15β,17α)-7,15:21,23-Diepoxy-6-hydroxy-4,8-dimethyl-1-oxo-18,24-dinor-11,12-secochola-2,13,20,22-tetraene-4,11-dicarboxylic Αcid γ-lactone Methyl Ester; NSC 309909; Nimbolide

Database IDs

• CAS Number: 25990-37-8
• PubChem SID: 164230927
• PubChem CID: 100017

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.1439662
• LogD (pH = 7.4): 3.1439662
• Log P: 3.1439662
• Molar Refractivity: 121.8649 cm^3
• Polarizability: 47.77502 Å^3
• Polar Surface Area: 92.04 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Light Beige Solid
• Melting Point: >223°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N476300

Nimbolide, a natural triterpenoid present in the edible parts of the neem tree (Azadirachta indica), was found to be growth-inhibitory in human colon carcinoma HT-29 cells. Nimbolide treatment of cells at 2.5 - 10 μM resulted in moderate to very strong gr

REFERENCES

• Khalid, S., et al.: J. Nat. Prod., 52, 922 (1989)
• Cohen, E., et al.: J. Life Sci., 58, 1075 (1989)
• Moragoda, L., et al.: Anticancer Res., 21, 873 (1989)
• Chang, K., et al.: Biochem. Pharmacol., 67, 717 (1989)
• Parsels, L., et al.: Cancer Res., 64, 6588