azadirachtin H

Details

• Internal ID: 6f383003-739b-4701-8172-e10f0a659bc1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (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-11-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)O)C(=O)OC)OC(=O)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1C[C@H]([C@]2(CO[C@@H]3[C@@H]2[C@]14CO[C@@H]([C@H]4[C@]([C@@H]3O)(C)[C@@]56[C@@H]7C[C@H]([C@@]5(O6)C)[C@]8(C=CO[C@H]8O7)O)O)C(=O)OC)OC(=O)C
• InChI: InChI=1S/C33H42O14/c1-7-14(2)24(36)45-17-11-18(44-15(3)34)31(26(38)40-6)13-42-20-21(31)30(17)12-43-25(37)22(30)28(4,23(20)35)33-19-10-16(29(33,5)47-33)32(39)8-9-41-27(32)46-19/h7-9,16-23,25,27,35,37,39H,10-13H2,1-6H3/b14-7+/t16-,17+,18-,19+,20-,21-,22+,23-,25+,27+,28+,29+,30+,31+,32+,33+/m1/s1
• InChI Key: ILMJTWSQVCYIKY-YAYGENDCSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₂O₁₄
• Molecular Weight: 662.70 g/mol
• Exact Mass: 662.25745601 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.25
• H-Bond Acceptor: 14
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 11Alpha-Azadirachtin H
• CHEBI:38510
• methyl (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-10a(8H)-carboxylate
• CHEMBL504820
• Q27117885
• methyl (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-11-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9483	94.83%
Caco-2	-	0.8282	82.82%
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	+	0.8122	81.22%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9233	92.33%
P-glycoprotein inhibitior	+	0.7219	72.19%
P-glycoprotein substrate	+	0.6791	67.91%
CYP3A4 substrate	+	0.7257	72.57%
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	+	0.7439	74.39%
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	-	0.9121	91.21%
Skin irritation	-	0.7081	70.81%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4556	45.56%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6453	64.53%
Acute Oral Toxicity (c)	I	0.6952	69.52%
Estrogen receptor binding	+	0.7965	79.65%
Androgen receptor binding	+	0.7456	74.56%
Thyroid receptor binding	+	0.5675	56.75%
Glucocorticoid receptor binding	+	0.6915	69.15%
Aromatase binding	+	0.6848	68.48%
PPAR gamma	+	0.7514	75.14%
Honey bee toxicity	-	0.9230	92.30%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
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	98.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.76%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.45%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.16%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.98%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	86.04%	91.19%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	85.40%	85.30%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.28%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.04%	89.50%
CHEMBL284	P27487	Dipeptidyl peptidase IV	84.81%	95.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.63%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.24%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.95%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.64%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.09%	97.14%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.95%	97.53%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.75%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.26%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.07%	95.89%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.93%	98.99%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.79%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.62%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	80.16%	90.17%

Plants that contains it

• Azadirachta excelsa
• Azadirachta indica

Cross-Links

• PubChem: 16722121
• NPASS: NPC5153
• LOTUS: LTS0022067
• wikiData: Q27117885