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

Details

• Internal ID: 2f335df9-0f69-486c-a00e-7987c4a4f1b9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (2R)-2-hydroxy-2-[(1S,2R,4S,5S,6S,10R,11S,12R,13R,14R,15R,17S,18S)-4,12,14-triacetyloxy-6-(furan-3-yl)-11,17-dihydroxy-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)O)C)C(C(=O)OC)O)C
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@@H]2[C@@]3([C@H]([C@]4(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)O)C)[C@H](C(=O)OC)O)C
• InChI: InChI=1S/C33H42O14/c1-14(34)44-20-10-19-31(6)24(23(38)28(39)42-7)29(4)13-32(31,40)22(26(29)45-15(2)35)27(46-16(3)36)33(19,41)18-11-21(37)47-25(30(18,20)5)17-8-9-43-12-17/h8-9,12,18-20,22-27,38,40-41H,10-11,13H2,1-7H3/t18-,19-,20+,22-,23-,24+,25+,26-,27-,29-,30+,31-,32+,33+/m1/s1
• InChI Key: QKTBSFGBXSKROA-QZKGHKDLSA-N
• Popularity: 1 reference 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): 205.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.38
• H-Bond Acceptor: 14
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9620	96.20%
Caco-2	-	0.8234	82.34%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6733	67.33%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.6905	69.05%
OATP1B3 inhibitior	-	0.3398	33.98%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8787	87.87%
P-glycoprotein inhibitior	+	0.7573	75.73%
P-glycoprotein substrate	+	0.6111	61.11%
CYP3A4 substrate	+	0.7067	70.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8340	83.40%
CYP3A4 inhibition	-	0.6918	69.18%
CYP2C9 inhibition	-	0.9004	90.04%
CYP2C19 inhibition	-	0.9267	92.67%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.6936	69.36%
CYP inhibitory promiscuity	-	0.9450	94.50%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4452	44.52%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8893	88.93%
Skin irritation	-	0.7045	70.45%
Skin corrosion	-	0.9167	91.67%
Ames mutagenesis	-	0.6464	64.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7790	77.90%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5571	55.71%
skin sensitisation	-	0.8934	89.34%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6050	60.50%
Acute Oral Toxicity (c)	I	0.5983	59.83%
Estrogen receptor binding	+	0.8102	81.02%
Androgen receptor binding	+	0.7292	72.92%
Thyroid receptor binding	+	0.5956	59.56%
Glucocorticoid receptor binding	+	0.7460	74.60%
Aromatase binding	+	0.7346	73.46%
PPAR gamma	+	0.7357	73.57%
Honey bee toxicity	-	0.7150	71.50%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9416	94.16%

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	99.66%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.51%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.13%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.37%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	93.87%	97.79%
CHEMBL2581	P07339	Cathepsin D	92.63%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.53%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.18%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	89.75%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.68%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.50%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.97%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.45%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.15%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.38%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.46%	95.56%
CHEMBL5028	O14672	ADAM10	82.17%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.47%	94.00%

Plants that contains it

• Xylocarpus granatum

Cross-Links

• PubChem: 11843450
• LOTUS: LTS0132060
• wikiData: Q105223308