methyl (1R,4S,5R,7S,8R,9R,10S,11S,12R)-7,11-dihydroxy-9-[(1S)-1-hydroxy-2-methoxy-2-oxoethyl]-10-[(1S,2S,6R,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-8,10-dimethyl-5-[(E)-2-methylbut-2-enoyl]oxy-2-oxatricyclo[6.3.1.04,12]dodecane-4-carboxylate

Details

• Internal ID: e7e3a519-9c5a-4cc5-9964-4ad06169b179
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (1R,4S,5R,7S,8R,9R,10S,11S,12R)-7,11-dihydroxy-9-[(1S)-1-hydroxy-2-methoxy-2-oxoethyl]-10-[(1S,2S,6R,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-8,10-dimethyl-5-[(E)-2-methylbut-2-enoyl]oxy-2-oxatricyclo[6.3.1.04,12]dodecane-4-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C2(C3C1(COC3C(C(C2C(C(=O)OC)O)(C)C45C6CC(C4(O5)C)C7(C=COC7O6)O)O)C(=O)OC)C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C[C@@H]([C@]2([C@@H]3[C@@]1(CO[C@H]3[C@H]([C@@]([C@@H]2[C@@H](C(=O)OC)O)(C)[C@@]45[C@@H]6C[C@H]([C@@]4(O5)C)[C@]7(C=CO[C@@H]7O6)O)O)C(=O)OC)C)O
• InChI: InChI=1S/C33H44O14/c1-8-14(2)24(37)45-17-12-16(34)28(3)21(19(35)25(38)41-6)29(4,23(36)20-22(28)31(17,13-44-20)26(39)42-7)33-18-11-15(30(33,5)47-33)32(40)9-10-43-27(32)46-18/h8-10,15-23,27,34-36,40H,11-13H2,1-7H3/b14-8+/t15-,16+,17-,18+,19+,20-,21-,22-,23-,27-,28-,29+,30+,31+,32+,33+/m1/s1
• InChI Key: JBYMKLQRMUTCTE-KPIKNLNOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₁₄
• Molecular Weight: 664.70 g/mol
• Exact Mass: 664.27310607 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.11
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9696	96.96%
Caco-2	-	0.8447	84.47%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7013	70.13%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.8216	82.16%
OATP1B3 inhibitior	+	0.9584	95.84%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7418	74.18%
P-glycoprotein inhibitior	+	0.7168	71.68%
P-glycoprotein substrate	+	0.7447	74.47%
CYP3A4 substrate	+	0.7366	73.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.5543	55.43%
CYP2C9 inhibition	-	0.8357	83.57%
CYP2C19 inhibition	-	0.8717	87.17%
CYP2D6 inhibition	-	0.9344	93.44%
CYP1A2 inhibition	-	0.8938	89.38%
CYP2C8 inhibition	+	0.7343	73.43%
CYP inhibitory promiscuity	-	0.8925	89.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5313	53.13%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.6642	66.42%
Skin corrosion	-	0.9243	92.43%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5803	58.03%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8435	84.35%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7973	79.73%
Acute Oral Toxicity (c)	I	0.5802	58.02%
Estrogen receptor binding	+	0.7747	77.47%
Androgen receptor binding	+	0.7496	74.96%
Thyroid receptor binding	+	0.5493	54.93%
Glucocorticoid receptor binding	+	0.7344	73.44%
Aromatase binding	+	0.6940	69.40%
PPAR gamma	+	0.7497	74.97%
Honey bee toxicity	-	0.8480	84.80%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9359	93.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.48%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.61%	94.45%
CHEMBL284	P27487	Dipeptidyl peptidase IV	93.35%	95.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.22%	89.00%
CHEMBL4302	P08183	P-glycoprotein 1	93.08%	92.98%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.53%	91.07%
CHEMBL2581	P07339	Cathepsin D	89.57%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.14%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.29%	97.25%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.86%	89.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.81%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.66%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.49%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.98%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.76%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.72%	92.62%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.34%	92.88%
CHEMBL221	P23219	Cyclooxygenase-1	83.11%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.69%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.34%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.41%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.40%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.10%	97.14%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.06%	85.31%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.89%	91.24%

Plants that contains it

• Azadirachta indica

Cross-Links

• PubChem: 101607410
• NPASS: NPC240820