methyl 2-[(1R,3R,4R,5R,10S,14S,15R,18S,19R,20R,22S)-3,22-diacetyloxy-5-(furan-3-yl)-15,16-dihydroxy-4,12,18,20-tetramethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.115,18.01,10.04,9.010,14.016,20]docos-8-en-19-yl]acetate

Details

• Internal ID: 512e17e7-086d-4d22-a54d-eaa1e86bdbb7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl 2-[(1R,3R,4R,5R,10S,14S,15R,18S,19R,20R,22S)-3,22-diacetyloxy-5-(furan-3-yl)-15,16-dihydroxy-4,12,18,20-tetramethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.115,18.01,10.04,9.010,14.016,20]docos-8-en-19-yl]acetate
• SMILES (Canonical): CC(=O)OC1CC23C4(C(C5(CC4(C(C5OC(=O)C)(C6C2(C7=CC(=O)OC(C17C)C8=COC=C8)OC(O6)(O3)C)O)O)C)CC(=O)OC)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@]23[C@@]4([C@@H]([C@@]5(CC4([C@@]([C@H]5OC(=O)C)([C@H]6[C@]2(C7=CC(=O)O[C@@H]([C@@]17C)C8=COC=C8)OC(O6)(O3)C)O)O)C)CC(=O)OC)C
• InChI: InChI=1S/C33H38O14/c1-15(34)42-20-12-31-28(5)18(10-21(36)40-7)26(3)14-30(28,38)32(39,24(26)43-16(2)35)25-33(31,47-29(6,45-25)46-31)19-11-22(37)44-23(27(19,20)4)17-8-9-41-13-17/h8-9,11,13,18,20,23-25,38-39H,10,12,14H2,1-7H3/t18-,20-,23-,24+,25+,26+,27-,28-,29?,30?,31-,32-,33+/m1/s1
• InChI Key: VCEYJROSLKNUID-CHIHQUSJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₈O₁₄
• Molecular Weight: 658.60 g/mol
• Exact Mass: 658.22615588 g/mol
• Topological Polar Surface Area (TPSA): 187.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 14
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9807	98.07%
Caco-2	-	0.8157	81.57%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7524	75.24%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	-	0.4423	44.23%
OATP1B3 inhibitior	+	0.8394	83.94%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9565	95.65%
P-glycoprotein inhibitior	+	0.7740	77.40%
P-glycoprotein substrate	+	0.7080	70.80%
CYP3A4 substrate	+	0.7284	72.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8747	87.47%
CYP3A4 inhibition	+	0.6353	63.53%
CYP2C9 inhibition	-	0.8073	80.73%
CYP2C19 inhibition	-	0.8286	82.86%
CYP2D6 inhibition	-	0.9234	92.34%
CYP1A2 inhibition	-	0.8460	84.60%
CYP2C8 inhibition	+	0.7469	74.69%
CYP inhibitory promiscuity	-	0.8467	84.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4331	43.31%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.8798	87.98%
Skin irritation	-	0.6312	63.12%
Skin corrosion	-	0.9326	93.26%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6642	66.42%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.5272	52.72%
skin sensitisation	-	0.8573	85.73%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6355	63.55%
Acute Oral Toxicity (c)	I	0.5665	56.65%
Estrogen receptor binding	+	0.7824	78.24%
Androgen receptor binding	+	0.7783	77.83%
Thyroid receptor binding	+	0.6301	63.01%
Glucocorticoid receptor binding	+	0.7585	75.85%
Aromatase binding	+	0.7370	73.70%
PPAR gamma	+	0.7336	73.36%
Honey bee toxicity	-	0.7202	72.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	99.89%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.90%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	96.43%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.60%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.97%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.50%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.17%	99.23%
CHEMBL4040	P28482	MAP kinase ERK2	87.07%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.00%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.02%	95.56%
CHEMBL2581	P07339	Cathepsin D	81.93%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.65%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.33%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.31%	95.89%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.14%	91.38%

Plants that contains it

• Xylocarpus granatum

Cross-Links

• PubChem: 101744757
• LOTUS: LTS0240140
• wikiData: Q104401660