(3aR,8aS,9aR)-8a-methyl-3-methylidene-3a,4,9,9a-tetrahydrobenzo[f][1]benzofuran-2,6-dione

Details

• Internal ID: 05078a3f-ebfc-4a5f-9340-d4875ee712d3
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (3aR,8aS,9aR)-8a-methyl-3-methylidene-3a,4,9,9a-tetrahydrobenzo[f][1]benzofuran-2,6-dione
• SMILES (Canonical): CC12CC3C(CC1=CC(=O)C=C2)C(=C)C(=O)O3
• SMILES (Isomeric): C[C@@]12C[C@@H]3[C@H](CC1=CC(=O)C=C2)C(=C)C(=O)O3
• InChI: InChI=1S/C14H14O3/c1-8-11-6-9-5-10(15)3-4-14(9,2)7-12(11)17-13(8)16/h3-5,11-12H,1,6-7H2,2H3/t11-,12-,14-/m1/s1
• InChI Key: CZHWYUJICFFNDV-YRGRVCCFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₃
• Molecular Weight: 230.26 g/mol
• Exact Mass: 230.094294304 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.95
• 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	+	0.6189	61.89%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6267	62.67%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	+	0.8597	85.97%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8862	88.62%
P-glycoprotein inhibitior	-	0.9281	92.81%
P-glycoprotein substrate	-	0.8462	84.62%
CYP3A4 substrate	+	0.5845	58.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9063	90.63%
CYP3A4 inhibition	-	0.7041	70.41%
CYP2C9 inhibition	-	0.8782	87.82%
CYP2C19 inhibition	-	0.6853	68.53%
CYP2D6 inhibition	-	0.9329	93.29%
CYP1A2 inhibition	+	0.5228	52.28%
CYP2C8 inhibition	-	0.6504	65.04%
CYP inhibitory promiscuity	-	0.7117	71.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4348	43.48%
Eye corrosion	-	0.9596	95.96%
Eye irritation	-	0.6241	62.41%
Skin irritation	+	0.4923	49.23%
Skin corrosion	-	0.8572	85.72%
Ames mutagenesis	-	0.7124	71.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4542	45.42%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.7461	74.61%
skin sensitisation	+	0.4875	48.75%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6060	60.60%
Acute Oral Toxicity (c)	III	0.6782	67.82%
Estrogen receptor binding	-	0.5908	59.08%
Androgen receptor binding	+	0.5724	57.24%
Thyroid receptor binding	-	0.8023	80.23%
Glucocorticoid receptor binding	-	0.6559	65.59%
Aromatase binding	-	0.7660	76.60%
PPAR gamma	-	0.7379	73.79%
Honey bee toxicity	-	0.7797	77.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9971	99.71%

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	95.67%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.52%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.17%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.23%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.21%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.64%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.31%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.17%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	82.73%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.64%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.70%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.32%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	80.19%	91.49%

Plants that contains it

• Artemisia xerophytica

Cross-Links

• PubChem: 162979361
• LOTUS: LTS0144455
• wikiData: Q104972806