4,11-dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-(acetyloxy)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11R)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate

• ChemBase ID: 160930
• Molecular Formular: C35H44O16
• Molecular Mass: 720.71426
• Monoisotopic Mass: 720.26293533
• SMILES: [C@]123[C@H]4[C@H]([C@H]([C@]([C@@H]1[C@](OC3)(C(=O)OC)O)([C@@]13[C@@H]5C[C@H]([C@]1(O3)C)[C@@]1(C=CO[C@H]1O5)O)C)O)OC[C@@]4([C@@H](C[C@@H]2OC(=O)/C(=C/C)/C)OC(=O)C)C(=O)OC
• Canonical SMILES: C/C=C(/C(=O)O[C@H]1C[C@@H](OC(=O)C)[C@@]2([C@H]3[C@@]41CO[C@]([C@H]4[C@@](C)([C@@H]([C@@H]3OC2)O)[C@@]12O[C@]2(C)[C@H]2C[C@@H]1O[C@H]1[C@@]2(O)C=CO1)(O)C(=O)OC)C(=O)OC)\C
• InChI: InChI=1S/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22-,23-,25+,28+,29-,30-,31+,32+,33-,34+,35+/m1/s1
• InChIKey: FTNJWQUOZFUQQJ-AUPHHXBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,11-dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-(acetyloxy)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11R)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^2,^6.0^9,^1^1]dodec-3-en-9-yl]-6-methyl-14-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0^1,^5.0^1^1,^1^5]pentadecane-4,11-dicarboxylate
• IUPAC Traditional name: 4,11-dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-(acetyloxy)-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11R)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^2,^6.0^9,^1^1]dodec-3-en-9-yl]-6-methyl-14-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0^1,^5.0^1^1,^1^5]pentadecane-4,11-dicarboxylate
• Synonyms: (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-(Acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-1H,7H-naphtho[1,8-bc:4,4a-c']difuran-5 10a(8H)-dicarboxylic Acid 5,10a-Dimethyl Ester; NeemAzal W; Neemazol; Neemgold; Nimbicidine; Nimurin; Oikos; Oikos 25 plus; Oikos 323 Bio; Ornazin; Safer BioNEEM; Suneem; Superneem; Azadirachtin; Align; Azatin; Azatin EC; Azatin Magnum; Azatin XL; BioNEEM; Ecozin; Gronim; NeemAzal F; NeemAzal T

Database IDs

• CAS Number: 11141-17-6
• PubChem SID: 162255065
• PubChem CID: 71313545

CALCULATED PROPERTIES

• Acid pKa: 9.429157
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): -0.13221195
• LogD (pH = 7.4): -0.13619894
• Log P: -0.13216089
• Molar Refractivity: 166.2389 cm^3
• Polarizability: 67.69091 Å^3
• Polar Surface Area: 215.34 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A797300

A tetranortriterpinoid isolated from the seeds of the neem tree. Highly active insect feeding deterrent and growth regulator. Isolation from A. indica and identification as feeding inhibitor in locusts. Used experimentally as insect control agent.

REFERENCES

• Gill, J.S., et al.: Nature, 232, 402 (1971)
• Klocke, J.A., et al.: Entomol. Exp. Appl., 32, 299 (1971)
• Kubo, I., Agric. Biol. Chem., 46, 1951 (1971)