3-(chloromethyl)-6-hydroxy-4,7,7-trimethyl-6,8-dihydro-3H-cyclopenta[g][2]benzofuran-1-one

Details

• Internal ID: 89298c9d-b6b3-4c53-9b9a-bad9804d1056
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Benzofuranones
• IUPAC Name: 3-(chloromethyl)-6-hydroxy-4,7,7-trimethyl-6,8-dihydro-3H-cyclopenta[g][2]benzofuran-1-one
• SMILES (Canonical): CC1=CC2=C(CC(C2O)(C)C)C3=C1C(OC3=O)CCl
• SMILES (Isomeric): CC1=CC2=C(CC(C2O)(C)C)C3=C1C(OC3=O)CCl
• InChI: InChI=1S/C15H17ClO3/c1-7-4-8-9(5-15(2,3)13(8)17)12-11(7)10(6-16)19-14(12)18/h4,10,13,17H,5-6H2,1-3H3
• InChI Key: VHKCWJAOPJXMDF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₇ClO₃
• Molecular Weight: 280.74 g/mol
• Exact Mass: 280.0866221 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.06
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.7267	72.67%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8016	80.16%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.8943	89.43%
OATP1B3 inhibitior	+	0.9330	93.30%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8528	85.28%
P-glycoprotein inhibitior	-	0.9124	91.24%
P-glycoprotein substrate	-	0.8644	86.44%
CYP3A4 substrate	+	0.6289	62.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8259	82.59%
CYP3A4 inhibition	-	0.5076	50.76%
CYP2C9 inhibition	-	0.6147	61.47%
CYP2C19 inhibition	-	0.6449	64.49%
CYP2D6 inhibition	-	0.9168	91.68%
CYP1A2 inhibition	-	0.5302	53.02%
CYP2C8 inhibition	-	0.7298	72.98%
CYP inhibitory promiscuity	-	0.7432	74.32%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7865	78.65%
Carcinogenicity (trinary)	Non-required	0.5150	51.50%
Eye corrosion	-	0.9753	97.53%
Eye irritation	-	0.7108	71.08%
Skin irritation	-	0.7050	70.50%
Skin corrosion	-	0.7687	76.87%
Ames mutagenesis	+	0.5646	56.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.6307	63.07%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.5322	53.22%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5390	53.90%
Acute Oral Toxicity (c)	III	0.4829	48.29%
Estrogen receptor binding	+	0.7814	78.14%
Androgen receptor binding	+	0.6431	64.31%
Thyroid receptor binding	+	0.7024	70.24%
Glucocorticoid receptor binding	-	0.4937	49.37%
Aromatase binding	-	0.8305	83.05%
PPAR gamma	+	0.6254	62.54%
Honey bee toxicity	-	0.9005	90.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9638	96.38%

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	97.73%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.86%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.20%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.44%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.61%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.05%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.59%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.21%	96.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.98%	93.03%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.92%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.31%	94.45%
CHEMBL4208	P20618	Proteasome component C5	81.67%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.13%	97.25%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 85240225
• LOTUS: LTS0276417
• wikiData: Q105286468