(3aR,4aR,5S,9aR)-4a,5-dimethyl-3-methylidene-3a,4,5,6,9,9a-hexahydrobenzo[f][1]benzofuran-2,7-dione

Details

• Internal ID: a51546b2-64f4-4f3c-b575-962aced9da0c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aR,4aR,5S,9aR)-4a,5-dimethyl-3-methylidene-3a,4,5,6,9,9a-hexahydrobenzo[f][1]benzofuran-2,7-dione
• SMILES (Canonical): CC1CC(=O)C=C2C1(CC3C(C2)OC(=O)C3=C)C
• SMILES (Isomeric): C[C@H]1CC(=O)C=C2[C@@]1(C[C@H]3[C@@H](C2)OC(=O)C3=C)C
• InChI: InChI=1S/C15H18O3/c1-8-4-11(16)5-10-6-13-12(7-15(8,10)3)9(2)14(17)18-13/h5,8,12-13H,2,4,6-7H2,1,3H3/t8-,12+,13+,15+/m0/s1
• InChI Key: YFLSVTSYJVWTFN-VFJFRJDUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8036	80.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6629	66.29%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.8580	85.80%
OATP1B3 inhibitior	+	0.9151	91.51%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9488	94.88%
P-glycoprotein inhibitior	-	0.8805	88.05%
P-glycoprotein substrate	-	0.8254	82.54%
CYP3A4 substrate	+	0.5519	55.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.6057	60.57%
CYP2C9 inhibition	-	0.9157	91.57%
CYP2C19 inhibition	-	0.7424	74.24%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.5648	56.48%
CYP2C8 inhibition	-	0.7743	77.43%
CYP inhibitory promiscuity	-	0.7923	79.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4916	49.16%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8364	83.64%
Skin irritation	+	0.4940	49.40%
Skin corrosion	-	0.8956	89.56%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4826	48.26%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.5394	53.94%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.6621	66.21%
Acute Oral Toxicity (c)	III	0.6968	69.68%
Estrogen receptor binding	-	0.5638	56.38%
Androgen receptor binding	+	0.5226	52.26%
Thyroid receptor binding	-	0.7505	75.05%
Glucocorticoid receptor binding	-	0.5494	54.94%
Aromatase binding	+	0.5650	56.50%
PPAR gamma	-	0.5792	57.92%
Honey bee toxicity	-	0.7787	77.87%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.01%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.86%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.62%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.09%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.28%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.58%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	88.02%	91.49%
CHEMBL2581	P07339	Cathepsin D	87.05%	98.95%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.25%	86.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.84%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.80%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.29%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.60%	97.14%

Plants that contains it

• Ondetia linearis

Cross-Links

• PubChem: 14357592
• LOTUS: LTS0152924
• wikiData: Q105347660