azadirachtin B

CNP0297629.1 · C33H42O14 · View on COCONUT ↗

2D Structure

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Identifiers

Name	azadirachtin B
IUPAC Name	dimethyl (1~{S},4~{S},5~{R},6~{S},7~{S},8~{R},11~{S},12~{R},14~{S},15~{R})-7,14-dihydroxy-6-[(1~{S},2~{S},6~{S},8~{S},9~{R},11~{S})-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6-methyl-12-[(~{E})-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4,11-dicarboxylate
COCONUT ID	CNP0297629.1
CAS	106500-25-8
InChIKey	USRBWQQLHKQWAV-ZGKQVQOISA-N
InChI	InChI=1S/C33H42O14/c1-7-14(2)24(36)45-17-11-16(34)30-12-44-20(25(37)40-5)21(30)28(3,23(35)19-22(30)31(17,13-43-19)26(38)41-6)33-18-10-15(29(33,4)47-33)32(39)8-9-42-27(32)46-18/h7-9,15-23,27,34-35,39H,10-13H2,1-6H3/b14-7+/t15-,16+,17-,18+,19-,20+,21+,22-,23-,27+,28+,29+,30-,31+,32+,33+/m1/s1
SMILES	C/C=C(\C)C(=O)O[C@@H]1C[C@H](O)[C@]23CO[C@H](C(=O)OC)[C@H]2[C@](C)([C@]24O[C@@]2(C)[C@H]2C[C@@H]4O[C@@H]4OC=C[C@@]42O)[C@H](O)[C@@H]2OC[C@@]1(C(=O)OC)[C@H]23

Properties

Molecular Formula	C33H42O14
Molecular Weight	662.69
Exact Mass	662.25746
Log P (ALogP)	-0.09
TPSA	189.04
H-Bond Donors / Acceptors	3 / 14
Rotatable Bonds	5
Lipinski's Rule of 5 Violations	2
QED Drug-likeness	0.15
NP-likeness	3.67

Classification

NP Pathway	Terpenoids
NP Superclass	Triterpenoids
NP Class	Limonoids
Chemical Superclass	Lipids and lipid-like molecules
Chemical Class	Prenol lipids
Chemical Subclass	Triterpenoids

Reported in GR-MAPs Plants

Azadirachta indica	as “Azadirachta indica” in COCONUT

References (9)

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.

COCONUT Compound