Azadirachtin

Details

• Internal ID: 714530c0-b476-421b-b1d2-6c1ddbf8ba35
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
• 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
• InChI Key: FTNJWQUOZFUQQJ-NDAWSKJSSA-N
• Popularity: 2,357 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₆
• Molecular Weight: 720.70 g/mol
• Exact Mass: 720.26293531 g/mol
• Topological Polar Surface Area (TPSA): 215.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 16
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• Azadirachtin A
• 11141-17-6
• Nimbicidine
• NeemAzal
• bioneem
• Nimurin
• Ornazin
• Azatin
• Suneem
• CHEBI:2942
• Superneem
• Ecozin
• Gronim
• Oikos
• Safer BioNEEM
• O4U1SAF85H
• BIOSAL
• DTXSID0037497
• NSC-368675
• azadyrachtin
• 1H,7H-Naphtho(1,8-bc:4,4a-c')difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(((2E)-2-methyl-1-oxo-2-butenyl)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)-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-
• dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
• dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-4,7-dihydroxy-6-((1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo(6.3.1.02,6.09,11)dodec-3-en-9-yl)-6-methyl-14-((E)-2-methylbut-2-enoyl)oxy-3,9-dioxatetracyclo(6.6.1.01,5.011,15)pentadecane-4,11-dicarboxylate
• RefChem:560444
• DTXCID8017497
• CHEBI:38473
• 601-089-4
• AZADIRACTIN
• C35H44O16
• Azadirachtin-A
• Align
• HSDB 7372
• dimethyl acetoxy-dihydroxy-[hydroxy(methyl)[?]yl]-methyl-[(E)-2-methylbut-2-enoyl]oxy-[?]dicarboxylate
• NSC 368675
• Azadirachtin (Standard)
• Azadirachtin 100 microg/mL in Acetonitrile
• AZADIRACHTIN [MI]
• UNII-O4U1SAF85H
• SCHEMBL27784
• CCRIS 9142
• CHEMBL509309
• orb1297455
• GLXC-23432
• MSK20401
• BDBM50634024
• AKOS040760284
• HY-126741R
• LMPR0106100001
• NCGC00163746-01
• DA-50844
• MS-31232
• HY-126741
• CS-0107060
• C08748
• Q793471
• 176087-49-3
• 1H,7H-Naphtho[1,8-bc:4,4a-c']difuran-5,10a(8H)-dicarboxylic acid, 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]-, 5,10a-dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-
• dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetoxy-4,7-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
• Dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2S,6S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
• dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-3,5-dihydroxy-4-[(1aR,2S,3aS,6aS,7S,7aS)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-4-methyl-8-{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-1H-naphtho[1,8a-c:4,5-b'c']difuran-5,10a(8H)-dicarboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9483	94.83%
Caco-2	-	0.8388	83.88%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7795	77.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8158	81.58%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9333	93.33%
P-glycoprotein inhibitior	+	0.7532	75.32%
P-glycoprotein substrate	+	0.7107	71.07%
CYP3A4 substrate	+	0.7371	73.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8843	88.43%
CYP3A4 inhibition	-	0.7696	76.96%
CYP2C9 inhibition	-	0.8452	84.52%
CYP2C19 inhibition	-	0.8327	83.27%
CYP2D6 inhibition	-	0.9435	94.35%
CYP1A2 inhibition	-	0.8868	88.68%
CYP2C8 inhibition	+	0.7599	75.99%
CYP inhibitory promiscuity	-	0.8863	88.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5886	58.86%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9077	90.77%
Skin irritation	-	0.7081	70.81%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5078	50.78%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6056	60.56%
Acute Oral Toxicity (c)	I	0.6952	69.52%
Estrogen receptor binding	+	0.7945	79.45%
Androgen receptor binding	+	0.7582	75.82%
Thyroid receptor binding	+	0.5692	56.92%
Glucocorticoid receptor binding	+	0.7255	72.55%
Aromatase binding	+	0.6819	68.19%
PPAR gamma	+	0.7531	75.31%
Honey bee toxicity	-	0.9679	96.79%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9698	96.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.60%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.16%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.97%	91.07%
CHEMBL284	P27487	Dipeptidyl peptidase IV	89.80%	95.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.35%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.87%	91.19%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	87.71%	96.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.36%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.20%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.07%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.02%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.96%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.48%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.40%	92.94%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.21%	85.30%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.77%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.75%	97.09%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.36%	97.53%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.96%	94.00%
CHEMBL4302	P08183	P-glycoprotein 1	81.91%	92.98%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.17%	89.34%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.04%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	80.82%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.63%	99.17%

Plants that contains it

• Azadirachta indica
• Turraea pubescens

Cross-Links

• PubChem: 5281303
• NPASS: NPC16729
• LOTUS: LTS0147769
• wikiData: Q793471