3-Ethyl-4-hydroxy-4-methyl-2-pentenoic acid (1R)-1,2,3,3abeta,4,5,6abeta,7,7aalpha,8,9,11a,11balpha,11c-tetradecahydro-1beta,2alpha-dihydroxy-10-(beta-D-glucopyranosyloxy)-3-(methoxycarbonyl)-8alpha,11abeta-dimethyl-5,9-dioxo-3beta,11cbeta-(epoxymethano)phenanthro[10,1-bc]pyran-4beta-yl ester

Details

• Internal ID: 058beccf-c096-4f1a-84ae-37b622ca4e50
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17S)-3-[(E)-3-ethyl-4-hydroxy-4-methylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylate
• SMILES (Canonical): CCC(=CC(=O)OC1C2C34COC2(C(C(C3C5(C=C(C(=O)C(C5CC4OC1=O)C)OC6C(C(C(C(O6)CO)O)O)O)C)O)O)C(=O)OC)C(C)(C)O
• SMILES (Isomeric): CC/C(=C\C(=O)O[C@@H]1[C@@H]2[C@@]34CO[C@@]2([C@H]([C@@H]([C@@H]3[C@]5(C=C(C(=O)[C@H]([C@@H]5C[C@H]4OC1=O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)O)C(=O)OC)/C(C)(C)O
• InChI: InChI=1S/C35H48O17/c1-7-14(32(3,4)46)8-19(37)52-25-27-34-12-48-35(27,31(45)47-6)28(43)24(42)26(34)33(5)10-16(20(38)13(2)15(33)9-18(34)51-29(25)44)49-30-23(41)22(40)21(39)17(11-36)50-30/h8,10,13,15,17-18,21-28,30,36,39-43,46H,7,9,11-12H2,1-6H3/b14-8+/t13-,15-,17+,18+,21+,22-,23+,24+,25+,26+,27+,28-,30+,33-,34+,35-/m0/s1
• InChI Key: BZHBPAJGRSEIHP-VHQGUAROSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₈O₁₇
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.28915006 g/mol
• Topological Polar Surface Area (TPSA): 265.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -2.23
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 3-Ethyl-4-hydroxy-4-methyl-2-pentenoic acid (1R)-1,2,3,3abeta,4,5,6abeta,7,7aalpha,8,9,11a,11balpha,11c-tetradecahydro-1beta,2alpha-dihydroxy-10-(beta-D-glucopyranosyloxy)-3-(methoxycarbonyl)-8alpha,11abeta-dimethyl-5,9-dioxo-3beta,11cbeta-(epoxymethano)phenanthro[10,1-bc]pyran-4beta-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8131	81.31%
Caco-2	-	0.8724	87.24%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7250	72.50%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8197	81.97%
OATP1B3 inhibitior	+	0.9383	93.83%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7976	79.76%
P-glycoprotein inhibitior	+	0.7375	73.75%
P-glycoprotein substrate	+	0.7703	77.03%
CYP3A4 substrate	+	0.7244	72.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8939	89.39%
CYP3A4 inhibition	-	0.8221	82.21%
CYP2C9 inhibition	-	0.8025	80.25%
CYP2C19 inhibition	-	0.8115	81.15%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	-	0.8774	87.74%
CYP2C8 inhibition	+	0.6925	69.25%
CYP inhibitory promiscuity	-	0.8222	82.22%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5908	59.08%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9110	91.10%
Skin irritation	-	0.7028	70.28%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4072	40.72%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.8514	85.14%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6064	60.64%
Acute Oral Toxicity (c)	III	0.6641	66.41%
Estrogen receptor binding	+	0.7847	78.47%
Androgen receptor binding	+	0.7418	74.18%
Thyroid receptor binding	-	0.5161	51.61%
Glucocorticoid receptor binding	+	0.7209	72.09%
Aromatase binding	+	0.6648	66.48%
PPAR gamma	+	0.7401	74.01%
Honey bee toxicity	-	0.6299	62.99%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9357	93.57%

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	99.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.14%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.99%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.44%	97.25%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.83%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.44%	89.34%
CHEMBL2581	P07339	Cathepsin D	94.23%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.71%	96.61%
CHEMBL2996	Q05655	Protein kinase C delta	91.33%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.52%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.95%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.13%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.18%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.78%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.36%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.69%	97.28%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.38%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.02%	96.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.60%	96.77%
CHEMBL5028	O14672	ADAM10	83.63%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.55%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.41%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.25%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.97%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.96%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	81.75%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.76%	96.21%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 11227971
• NPASS: NPC140045
• LOTUS: LTS0249612
• wikiData: Q104950458