methyl (1S,2R,3S,4R,8R,9S,10R,13R,15R)-2-acetyloxy-13-(furan-3-yl)-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.03,8.011,15]hexadeca-5,11-diene-4-carboxylate

Details

• Internal ID: 62a8641e-6d7f-4068-a8e9-16f2ab861280
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (1S,2R,3S,4R,8R,9S,10R,13R,15R)-2-acetyloxy-13-(furan-3-yl)-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.03,8.011,15]hexadeca-5,11-diene-4-carboxylate
• SMILES (Canonical): CC1=C2C(CC1C3=COC=C3)OC4C2(C(C5(C(C4OC(=O)C)C(C=CC5=O)(C)C(=O)OC)C)CC(=O)OC)C
• SMILES (Isomeric): CC1=C2[C@@H](C[C@H]1C3=COC=C3)O[C@H]4[C@@]2([C@@H]([C@@]5([C@H]([C@H]4OC(=O)C)[C@](C=CC5=O)(C)C(=O)OC)C)CC(=O)OC)C
• InChI: InChI=1S/C30H36O9/c1-15-18(17-9-11-37-14-17)12-19-23(15)30(5)20(13-22(33)35-6)29(4)21(32)8-10-28(3,27(34)36-7)25(29)24(26(30)39-19)38-16(2)31/h8-11,14,18-20,24-26H,12-13H2,1-7H3/t18-,19-,20-,24-,25-,26-,28-,29+,30-/m1/s1
• InChI Key: NHOIBRJOQAYBJT-ZXGOAPHISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₆O₉
• Molecular Weight: 540.60 g/mol
• Exact Mass: 540.23593272 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 3.92
• H-Bond Acceptor: 9
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	-	0.6503	65.03%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7499	74.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3345	33.45%
OATP1B3 inhibitior	-	0.2438	24.38%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9929	99.29%
P-glycoprotein inhibitior	+	0.9044	90.44%
P-glycoprotein substrate	+	0.6517	65.17%
CYP3A4 substrate	+	0.7084	70.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8814	88.14%
CYP3A4 inhibition	+	0.7765	77.65%
CYP2C9 inhibition	-	0.7680	76.80%
CYP2C19 inhibition	-	0.7579	75.79%
CYP2D6 inhibition	-	0.9214	92.14%
CYP1A2 inhibition	-	0.8433	84.33%
CYP2C8 inhibition	+	0.7320	73.20%
CYP inhibitory promiscuity	+	0.6988	69.88%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Danger	0.5004	50.04%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8857	88.57%
Skin irritation	-	0.7052	70.52%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7980	79.80%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	+	0.6043	60.43%
skin sensitisation	-	0.7667	76.67%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4808	48.08%
Acute Oral Toxicity (c)	III	0.7700	77.00%
Estrogen receptor binding	+	0.8400	84.00%
Androgen receptor binding	+	0.7318	73.18%
Thyroid receptor binding	+	0.6408	64.08%
Glucocorticoid receptor binding	+	0.8579	85.79%
Aromatase binding	+	0.6207	62.07%
PPAR gamma	+	0.8202	82.02%
Honey bee toxicity	-	0.7264	72.64%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9845	98.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.63%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.38%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.23%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.01%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.62%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.87%	95.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	91.84%	81.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.78%	86.33%
CHEMBL4208	P20618	Proteasome component C5	89.29%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.75%	95.56%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	87.48%	87.67%
CHEMBL3401	O75469	Pregnane X receptor	86.76%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.40%	96.00%
CHEMBL4040	P28482	MAP kinase ERK2	84.12%	83.82%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.80%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.66%	89.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.80%	83.10%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.64%	92.62%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.63%	90.24%
CHEMBL340	P08684	Cytochrome P450 3A4	80.58%	91.19%
CHEMBL2581	P07339	Cathepsin D	80.49%	98.95%
CHEMBL5028	O14672	ADAM10	80.33%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.11%	99.17%

Plants that contains it

• Azadirachta indica
• Centaurea sinaica
• Chisocheton ceramicus
• Cleome spinosa
• Daphniphyllum himalense subsp. angustifolium
• Goniothalamus giganteus
• Marcetella moquiniana
• Melochia corchorifolia
• Phalaenopsis schilleriana
• Stachys palustris
• Walsura trifoliolata

Cross-Links

• PubChem: 93473232
• NPASS: NPC42264