(2S)-2-[(4-chlorophenyl)methyl]-2-hydroxy-1-benzofuran-3-one

Details

• Internal ID: 6c5a035c-2fed-4984-8644-456800b5974f
• Taxonomy: Phenylpropanoids and polyketides > Aurone flavonoids > Auronols
• IUPAC Name: (2S)-2-[(4-chlorophenyl)methyl]-2-hydroxy-1-benzofuran-3-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C(O2)(CC3=CC=C(C=C3)Cl)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)[C@@](O2)(CC3=CC=C(C=C3)Cl)O
• InChI: InChI=1S/C15H11ClO3/c16-11-7-5-10(6-8-11)9-15(18)14(17)12-3-1-2-4-13(12)19-15/h1-8,18H,9H2/t15-/m0/s1
• InChI Key: SGHMQSOFJHQKCW-HNNXBMFYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₁ClO₃
• Molecular Weight: 274.70 g/mol
• Exact Mass: 274.0396719 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.85
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.6436	64.36%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6213	62.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9024	90.24%
OATP1B3 inhibitior	+	0.8838	88.38%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6321	63.21%
P-glycoprotein inhibitior	-	0.8974	89.74%
P-glycoprotein substrate	-	0.9669	96.69%
CYP3A4 substrate	+	0.5678	56.78%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.7451	74.51%
CYP3A4 inhibition	-	0.7593	75.93%
CYP2C9 inhibition	-	0.7010	70.10%
CYP2C19 inhibition	-	0.8021	80.21%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	-	0.7317	73.17%
CYP2C8 inhibition	-	0.5791	57.91%
CYP inhibitory promiscuity	-	0.6154	61.54%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7668	76.68%
Carcinogenicity (trinary)	Danger	0.5071	50.71%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.6221	62.21%
Skin irritation	-	0.5406	54.06%
Skin corrosion	-	0.9519	95.19%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6383	63.83%
Micronuclear	+	0.6158	61.58%
Hepatotoxicity	+	0.5824	58.24%
skin sensitisation	-	0.5443	54.43%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7928	79.28%
Acute Oral Toxicity (c)	II	0.4435	44.35%
Estrogen receptor binding	-	0.4769	47.69%
Androgen receptor binding	+	0.7216	72.16%
Thyroid receptor binding	-	0.5205	52.05%
Glucocorticoid receptor binding	-	0.8400	84.00%
Aromatase binding	+	0.6063	60.63%
PPAR gamma	+	0.7150	71.50%
Honey bee toxicity	-	0.7996	79.96%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9733	97.33%

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	96.90%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.95%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.95%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.55%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.48%	94.73%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	89.38%	92.17%
CHEMBL1944	P08473	Neprilysin	88.15%	92.63%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.13%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.85%	86.33%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.07%	90.24%
CHEMBL5957	P21589	5'-nucleotidase	85.83%	97.78%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.00%	96.95%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	84.93%	85.94%
CHEMBL4208	P20618	Proteasome component C5	82.24%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.51%	86.92%

Plants that contains it

• Tetradium ruticarpum

Cross-Links

• PubChem: 101077897
• NPASS: NPC286735