(3aR,9aR)-5,8-dimethyl-3-methylidene-3a,4,9,9a-tetrahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 54fd17fd-d12c-4407-8e42-ab58e80a0bfb
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (3aR,9aR)-5,8-dimethyl-3-methylidene-3a,4,9,9a-tetrahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2CC3C(CC2=C(C=C1)C)OC(=O)C3=C
• SMILES (Isomeric): CC1=C2C[C@H]3[C@@H](CC2=C(C=C1)C)OC(=O)C3=C
• InChI: InChI=1S/C15H16O2/c1-8-4-5-9(2)12-7-14-13(6-11(8)12)10(3)15(16)17-14/h4-5,13-14H,3,6-7H2,1-2H3/t13-,14-/m1/s1
• InChI Key: GTRAODQPIPVSKC-ZIAGYGMSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₂
• Molecular Weight: 228.29 g/mol
• Exact Mass: 228.115029749 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.50
• H-Bond Acceptor: 2
• 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	+	0.7907	79.07%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5469	54.69%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.9435	94.35%
OATP1B3 inhibitior	+	0.9401	94.01%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7395	73.95%
P-glycoprotein inhibitior	-	0.8623	86.23%
P-glycoprotein substrate	-	0.9512	95.12%
CYP3A4 substrate	-	0.5755	57.55%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8100	81.00%
CYP3A4 inhibition	+	0.5460	54.60%
CYP2C9 inhibition	-	0.8368	83.68%
CYP2C19 inhibition	+	0.7897	78.97%
CYP2D6 inhibition	-	0.9207	92.07%
CYP1A2 inhibition	+	0.7771	77.71%
CYP2C8 inhibition	-	0.8477	84.77%
CYP inhibitory promiscuity	+	0.7239	72.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4744	47.44%
Eye corrosion	-	0.9719	97.19%
Eye irritation	-	0.6693	66.93%
Skin irritation	-	0.6232	62.32%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6487	64.87%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.8875	88.75%
skin sensitisation	+	0.6844	68.44%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6991	69.91%
Acute Oral Toxicity (c)	III	0.6112	61.12%
Estrogen receptor binding	-	0.8147	81.47%
Androgen receptor binding	-	0.5968	59.68%
Thyroid receptor binding	-	0.5879	58.79%
Glucocorticoid receptor binding	-	0.5547	55.47%
Aromatase binding	-	0.8003	80.03%
PPAR gamma	-	0.6133	61.33%
Honey bee toxicity	-	0.8669	86.69%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9972	99.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.26%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	86.59%	91.49%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.65%	93.65%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.31%	91.11%
CHEMBL2581	P07339	Cathepsin D	83.11%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.60%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.91%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	81.89%	94.73%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.32%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.23%	86.33%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.20%	86.00%

Plants that contains it

• Artemisia reptans
• Ferreyranthus fruticosus

Cross-Links

• PubChem: 14021294
• LOTUS: LTS0152150
• wikiData: Q105019293