[(1S,4R,5R,10R,12S,14R,15S,16R,18R,19S,20R,22S)-19-[(1S)-1-acetyloxy-2-methoxy-2-oxoethyl]-12-[(2R)-butan-2-yl]-5-(furan-3-yl)-15,16-dihydroxy-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.115,18.01,10.04,9.010,14.016,20]docos-8-en-22-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: d826bf1e-784d-4b01-a485-70f5b75dae3b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,4R,5R,10R,12S,14R,15S,16R,18R,19S,20R,22S)-19-[(1S)-1-acetyloxy-2-methoxy-2-oxoethyl]-12-[(2R)-butan-2-yl]-5-(furan-3-yl)-15,16-dihydroxy-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.115,18.01,10.04,9.010,14.016,20]docos-8-en-22-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CCC(C)C12OC3C4(C(C5(CC4(C(C5C(C(=O)OC)OC(=O)C)(C6(C3(O1)C7=CC(=O)OC(C7(CC6)C)C8=COC=C8)O2)C)O)C)OC(=O)C(=CC)C)O
• SMILES (Isomeric): CC[C@@H](C)[C@@]12O[C@@H]3[C@]4([C@H]([C@@]5(C[C@]4([C@@]([C@H]5[C@@H](C(=O)OC)OC(=O)C)([C@@]6([C@@]3(O1)C7=CC(=O)O[C@H]([C@@]7(CC6)C)C8=COC=C8)O2)C)O)C)OC(=O)/C(=C/C)/C)O
• InChI: InChI=1S/C39H48O14/c1-10-19(3)28(42)50-30-33(7)18-35(44)34(8,26(33)25(29(43)46-9)48-21(5)40)36-14-13-32(6)23(16-24(41)49-27(32)22-12-15-47-17-22)38(36)31(37(30,35)45)51-39(52-36,53-38)20(4)11-2/h10,12,15-17,20,25-27,30-31,44-45H,11,13-14,18H2,1-9H3/b19-10+/t20-,25+,26+,27+,30+,31-,32-,33-,34-,35-,36+,37+,38-,39+/m1/s1
• InChI Key: KSEZWHNEWCMXKZ-NANRVLCDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₈O₁₄
• Molecular Weight: 740.80 g/mol
• Exact Mass: 740.30440620 g/mol
• Topological Polar Surface Area (TPSA): 187.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.73
• H-Bond Acceptor: 14
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9851	98.51%
Caco-2	-	0.8295	82.95%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7729	77.29%
OATP2B1 inhibitior	-	0.5763	57.63%
OATP1B1 inhibitior	+	0.7277	72.77%
OATP1B3 inhibitior	-	0.2184	21.84%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9872	98.72%
P-glycoprotein inhibitior	+	0.8028	80.28%
P-glycoprotein substrate	+	0.7393	73.93%
CYP3A4 substrate	+	0.7382	73.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8840	88.40%
CYP3A4 inhibition	+	0.7017	70.17%
CYP2C9 inhibition	-	0.7542	75.42%
CYP2C19 inhibition	-	0.7928	79.28%
CYP2D6 inhibition	-	0.9080	90.80%
CYP1A2 inhibition	-	0.8001	80.01%
CYP2C8 inhibition	+	0.7550	75.50%
CYP inhibitory promiscuity	-	0.7656	76.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4393	43.93%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.5975	59.75%
Skin corrosion	-	0.9166	91.66%
Ames mutagenesis	-	0.5940	59.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.7309	73.09%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5701	57.01%
skin sensitisation	-	0.8632	86.32%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7792	77.92%
Acute Oral Toxicity (c)	II	0.4077	40.77%
Estrogen receptor binding	+	0.7844	78.44%
Androgen receptor binding	+	0.7748	77.48%
Thyroid receptor binding	+	0.6434	64.34%
Glucocorticoid receptor binding	+	0.7833	78.33%
Aromatase binding	+	0.7020	70.20%
PPAR gamma	+	0.7721	77.21%
Honey bee toxicity	-	0.6644	66.44%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9893	98.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.57%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.75%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.67%	97.25%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.18%	91.24%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.01%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.62%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	92.24%	90.17%
CHEMBL2581	P07339	Cathepsin D	91.30%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.59%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	90.34%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.78%	99.23%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.67%	91.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.19%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.76%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.96%	91.07%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.28%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.42%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.62%	100.00%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	83.37%	92.95%
CHEMBL255	P29275	Adenosine A2b receptor	82.83%	98.59%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.50%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.99%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.03%	100.00%

Plants that contains it

• Swietenia macrophylla

Cross-Links

• PubChem: 163186638
• LOTUS: LTS0175626
• wikiData: Q105145389