(4aS,8R,8aR)-8-hydroxy-3,8a-dimethyl-5-methylidene-4a,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 64673996-2ff8-4b5e-bdc1-a1c10dd80cab
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (4aS,8R,8aR)-8-hydroxy-3,8a-dimethyl-5-methylidene-4a,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2CC3C(=C)CCC(C3(C=C2OC1=O)C)O
• SMILES (Isomeric): CC1=C2C[C@H]3C(=C)CC[C@H]([C@]3(C=C2OC1=O)C)O
• InChI: InChI=1S/C15H18O3/c1-8-4-5-13(16)15(3)7-12-10(6-11(8)15)9(2)14(17)18-12/h7,11,13,16H,1,4-6H2,2-3H3/t11-,13+,15-/m0/s1
• InChI Key: OAKMFBHDBVZTBA-LNSITVRQSA-N
• Popularity: 0 references 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): 46.50 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	+	0.6966	69.66%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7929	79.29%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.8772	87.72%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5401	54.01%
BSEP inhibitior	-	0.8028	80.28%
P-glycoprotein inhibitior	-	0.9253	92.53%
P-glycoprotein substrate	-	0.9030	90.30%
CYP3A4 substrate	+	0.5785	57.85%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	-	0.5917	59.17%
CYP2C9 inhibition	-	0.9254	92.54%
CYP2C19 inhibition	-	0.7197	71.97%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.7245	72.45%
CYP2C8 inhibition	-	0.9029	90.29%
CYP inhibitory promiscuity	-	0.9032	90.32%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5125	51.25%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.8458	84.58%
Skin irritation	+	0.5365	53.65%
Skin corrosion	-	0.9112	91.12%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3784	37.84%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.7658	76.58%
skin sensitisation	-	0.6698	66.98%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.5856	58.56%
Acute Oral Toxicity (c)	III	0.5256	52.56%
Estrogen receptor binding	-	0.4890	48.90%
Androgen receptor binding	-	0.4837	48.37%
Thyroid receptor binding	+	0.5188	51.88%
Glucocorticoid receptor binding	+	0.7097	70.97%
Aromatase binding	-	0.6184	61.84%
PPAR gamma	-	0.4916	49.16%
Honey bee toxicity	-	0.9232	92.32%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9898	98.98%

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	94.12%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.46%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.69%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.42%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.05%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.57%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.51%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.82%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.79%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.14%	86.33%

Plants that contains it

• Neolitsea acuminatissima

Cross-Links

• PubChem: 162888130
• LOTUS: LTS0090847
• wikiData: Q105188713