(2S)-2-[(3,4-dihydroxyphenyl)methyl]-2,6-dihydroxy-1-benzofuran-3-one

Details

• Internal ID: 7984098d-d02f-464c-869c-bb273febd85d
• Taxonomy: Phenylpropanoids and polyketides > Aurone flavonoids > Auronols
• IUPAC Name: (2S)-2-[(3,4-dihydroxyphenyl)methyl]-2,6-dihydroxy-1-benzofuran-3-one
• SMILES (Canonical): C1=CC(=C(C=C1CC2(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@]2(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
• InChI: InChI=1S/C15H12O6/c16-9-2-3-10-13(6-9)21-15(20,14(10)19)7-8-1-4-11(17)12(18)5-8/h1-6,16-18,20H,7H2/t15-/m0/s1
• InChI Key: LCHNFNNYVOUXRN-HNNXBMFYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8999	89.99%
Caco-2	-	0.7310	73.10%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6752	67.52%
OATP2B1 inhibitior	-	0.5706	57.06%
OATP1B1 inhibitior	+	0.9063	90.63%
OATP1B3 inhibitior	+	0.9306	93.06%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7553	75.53%
P-glycoprotein inhibitior	-	0.9515	95.15%
P-glycoprotein substrate	-	0.8586	85.86%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7498	74.98%
CYP3A4 inhibition	-	0.7910	79.10%
CYP2C9 inhibition	-	0.8045	80.45%
CYP2C19 inhibition	-	0.8265	82.65%
CYP2D6 inhibition	-	0.8767	87.67%
CYP1A2 inhibition	-	0.7878	78.78%
CYP2C8 inhibition	-	0.5912	59.12%
CYP inhibitory promiscuity	-	0.8390	83.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4305	43.05%
Eye corrosion	-	0.9913	99.13%
Eye irritation	+	0.8981	89.81%
Skin irritation	-	0.5641	56.41%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9037	90.37%
Micronuclear	+	0.7718	77.18%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7466	74.66%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6399	63.99%
Acute Oral Toxicity (c)	III	0.3102	31.02%
Estrogen receptor binding	+	0.7446	74.46%
Androgen receptor binding	+	0.7862	78.62%
Thyroid receptor binding	+	0.5897	58.97%
Glucocorticoid receptor binding	+	0.6844	68.44%
Aromatase binding	+	0.7263	72.63%
PPAR gamma	+	0.5899	58.99%
Honey bee toxicity	-	0.8140	81.40%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9467	94.67%

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	99.27%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.99%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.95%	95.56%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.39%	80.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.52%	99.15%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.27%	96.95%
CHEMBL4208	P20618	Proteasome component C5	85.70%	90.00%
CHEMBL3194	P02766	Transthyretin	85.63%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.30%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.72%	96.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.64%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.91%	89.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.97%	85.11%
CHEMBL242	Q92731	Estrogen receptor beta	81.89%	98.35%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.20%	94.00%

Plants that contains it

• Xanthocercis zambesiaca

Cross-Links

• PubChem: 163025545
• LOTUS: LTS0160373
• wikiData: Q105149827