methyl 9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate

Details

• Internal ID: ad474407-3437-48f3-a4af-8125506c02ec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: methyl 9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
• SMILES (Canonical): CC(=O)OC1CC(C2(CCC3C(=O)OC(CC3(C2C1=O)C)C4=COC=C4)C)C(=O)OC
• SMILES (Isomeric): CC(=O)OC1CC(C2(CCC3C(=O)OC(CC3(C2C1=O)C)C4=COC=C4)C)C(=O)OC
• InChI: InChI=1S/C23H28O8/c1-12(24)30-16-9-15(20(26)28-4)22(2)7-5-14-21(27)31-17(13-6-8-29-11-13)10-23(14,3)19(22)18(16)25/h6,8,11,14-17,19H,5,7,9-10H2,1-4H3
• InChI Key: OBSYBRPAKCASQB-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₈
• Molecular Weight: 432.50 g/mol
• Exact Mass: 432.17841785 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• DTXSID80868746
• OBSYBRPAKCASQB-UHFFFAOYSA-N
• NSC_128563
• CAS_83729-01-5
• FT-0674513
• L000741
• Methyl 9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxododecahydro-2H-naphtho[2,1-c]pyran-7-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9786	97.86%
Caco-2	-	0.5646	56.46%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7603	76.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3903	39.03%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8157	81.57%
P-glycoprotein inhibitior	+	0.6979	69.79%
P-glycoprotein substrate	+	0.5398	53.98%
CYP3A4 substrate	+	0.7064	70.64%
CYP2C9 substrate	-	0.5906	59.06%
CYP2D6 substrate	-	0.8292	82.92%
CYP3A4 inhibition	-	0.5539	55.39%
CYP2C9 inhibition	-	0.9239	92.39%
CYP2C19 inhibition	-	0.8944	89.44%
CYP2D6 inhibition	-	0.9479	94.79%
CYP1A2 inhibition	-	0.8486	84.86%
CYP2C8 inhibition	-	0.5761	57.61%
CYP inhibitory promiscuity	-	0.9074	90.74%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5504	55.04%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9250	92.50%
Skin irritation	-	0.7222	72.22%
Skin corrosion	-	0.8697	86.97%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9105	91.05%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6157	61.57%
skin sensitisation	-	0.9199	91.99%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7094	70.94%
Acute Oral Toxicity (c)	I	0.3955	39.55%
Estrogen receptor binding	+	0.8637	86.37%
Androgen receptor binding	+	0.6890	68.90%
Thyroid receptor binding	+	0.5625	56.25%
Glucocorticoid receptor binding	+	0.8054	80.54%
Aromatase binding	+	0.5209	52.09%
PPAR gamma	+	0.6124	61.24%
Honey bee toxicity	-	0.7511	75.11%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9779	97.79%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL237	P41145	Kappa opioid receptor	0.015 nM; 41 nM; 17 nM; 1.3 nM; 6.5 nM; 140 nM	EC50; Ki; Ki; Ki; EC50; Ki	via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.64%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.27%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.19%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.33%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.11%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.05%	89.00%
CHEMBL3524	P56524	Histone deacetylase 4	88.05%	92.97%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.13%	92.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.70%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.58%	82.69%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.77%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.73%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.70%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.61%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.44%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.45%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.45%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.37%	95.71%

Plants that contains it

• Salvia divinorum

Cross-Links

• PubChem: 3969708
• LOTUS: LTS0254958
• wikiData: Q105189156