4,11-dimethyl (8R,11S,14S,15R)-12-(acetyloxy)-4,7-dihydroxy-6-{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: 133813
• Molecular Formular: C35H44O16
• Molecular Mass: 720.71426
• Monoisotopic Mass: 720.26293533
• SMILES: C/C=C(\C)/C(=O)O[C@H]1CC([C@]2(CO[C@@H]3[C@@H]2C21COC(C2C(C3O)(C)C12C3CC(C1(O2)C)C1(C=COC1O3)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
• Canonical SMILES: C/C=C(/C(=O)O[C@H]1CC(OC(=O)C)[C@@]2([C@H]3C41COC(C4C(C)(C([C@@H]3OC2)O)C12OC2(C)C2CC1OC1C2(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?/m0/s1
• InChIKey: FTNJWQUOZFUQQJ-AWFKZVNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,11-dimethyl (8R,11S,14S,15R)-12-(acetyloxy)-4,7-dihydroxy-6-{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; 4,11-dimethyl (8R,11S,14S,15R)-12-(acetyloxy)-4,7-dihydroxy-6-{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-[(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 (8R,11S,14S,15R)-12-(acetyloxy)-4,7-dihydroxy-6-{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; 4,11-dimethyl (8R,11S,14S,15R)-12-(acetyloxy)-4,7-dihydroxy-6-{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-[(2-methylbut-2-enoyl)oxy]-3,9-dioxatetracyclo[6.6.1.0^1,^5.0^1^1,^1^5]pentadecane-4,11-dicarboxylate
• Synonyms: Azadirachtin; 印楝素

Database IDs

• CAS Number: 11141-17-6
• MDL Number: MFCD00083241
• PubChem SID: 24891232; 162228090; 24899162
• PubChem CID: 71308720

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

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~95%
• Grade: analytical standard
• Packaging: ampule of 10 mg
• Empirical Formula (Hill Notation): C35H44O16

DETAILS

Sigma Aldrich - A7430

Biochem/physiol Actions
Triterpenoid found in need tree seeds, azadiractin suppresses feeding by many insect species and disrupts growth of most insect and other arthropod species, while having very low mammalian toxicity. Promising as a natural pesticide.1

Sigma Aldrich - PS2075

General description
Crude extract of the neem tree. Not intended for use as a quantitative standard
Biochem/physiol Actions
Triterpenoid found in need tree seeds, azadiractin suppresses feeding by many insect species and disrupts growth of most insect and other arthropod species, while having very low mammalian toxicity. Promising as a natural pesticide.1