methyl (2S)-2-hydroxy-2-[(1S,2R,4S,5S,6S,10R,11S,12R,13R,14R,17S,18S)-4,12,14,17-tetraacetyloxy-6-(furan-3-yl)-11-hydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.02,11.05,10.013,17]octadecan-18-yl]acetate

Details

• Internal ID: 6ba2d6d0-70dd-4d01-b416-dcb0e203a6f5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (2S)-2-hydroxy-2-[(1S,2R,4S,5S,6S,10R,11S,12R,13R,14R,17S,18S)-4,12,14,17-tetraacetyloxy-6-(furan-3-yl)-11-hydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.02,11.05,10.013,17]octadecan-18-yl]acetate
• SMILES (Canonical): CC(=O)OC1CC2C3(C(C4(CC3(C(C4OC(=O)C)C(C2(C5C1(C(OC(=O)C5)C6=COC=C6)C)O)OC(=O)C)OC(=O)C)C)C(C(=O)OC)O)C
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@@H]2[C@@]3([C@H](C4(C[C@@]3([C@H]([C@H]4OC(=O)C)[C@H]([C@@]2([C@H]5[C@@]1([C@@H](OC(=O)C5)C6=COC=C6)C)O)OC(=O)C)OC(=O)C)C)[C@@H](C(=O)OC)O)C
• InChI: InChI=1S/C35H44O15/c1-15(36)46-22-11-21-33(7)26(25(41)30(42)44-8)31(5)14-34(33,50-18(4)39)24(28(31)47-16(2)37)29(48-17(3)38)35(21,43)20-12-23(40)49-27(32(20,22)6)19-9-10-45-13-19/h9-10,13,20-22,24-29,41,43H,11-12,14H2,1-8H3/t20-,21-,22+,24-,25+,26+,27+,28-,29-,31?,32+,33-,34+,35+/m1/s1
• InChI Key: WWFHQTXLMHPBRD-AOPLNZKNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₅
• Molecular Weight: 704.70 g/mol
• Exact Mass: 704.26802069 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.95
• H-Bond Acceptor: 15
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9487	94.87%
Caco-2	-	0.8219	82.19%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7306	73.06%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.6958	69.58%
OATP1B3 inhibitior	-	0.3504	35.04%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9208	92.08%
P-glycoprotein inhibitior	+	0.7833	78.33%
P-glycoprotein substrate	+	0.6108	61.08%
CYP3A4 substrate	+	0.7125	71.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8340	83.40%
CYP3A4 inhibition	-	0.7510	75.10%
CYP2C9 inhibition	-	0.8658	86.58%
CYP2C19 inhibition	-	0.9008	90.08%
CYP2D6 inhibition	-	0.9397	93.97%
CYP1A2 inhibition	-	0.8731	87.31%
CYP2C8 inhibition	+	0.7244	72.44%
CYP inhibitory promiscuity	-	0.8997	89.97%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4645	46.45%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.8873	88.73%
Skin irritation	-	0.7328	73.28%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	-	0.6364	63.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7282	72.82%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5071	50.71%
skin sensitisation	-	0.8981	89.81%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6413	64.13%
Acute Oral Toxicity (c)	I	0.6284	62.84%
Estrogen receptor binding	+	0.8070	80.70%
Androgen receptor binding	+	0.7391	73.91%
Thyroid receptor binding	+	0.6049	60.49%
Glucocorticoid receptor binding	+	0.7807	78.07%
Aromatase binding	+	0.7493	74.93%
PPAR gamma	+	0.7503	75.03%
Honey bee toxicity	-	0.6998	69.98%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9589	95.89%

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	99.75%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.94%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.14%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.06%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	94.43%	97.79%
CHEMBL2581	P07339	Cathepsin D	91.98%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.83%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.45%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	91.41%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.05%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.02%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.49%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.81%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.76%	97.14%
CHEMBL5028	O14672	ADAM10	84.09%	97.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.62%	95.71%
CHEMBL299	P17252	Protein kinase C alpha	82.19%	98.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.59%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.64%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.61%	95.89%

Plants that contains it

• Antirrhinum majus
• Vanilla planifolia
• Xylocarpus granatum

Cross-Links

• PubChem: 102086518
• LOTUS: LTS0215761
• wikiData: Q82099403