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

Details

• Internal ID: 302b1618-e442-478a-883c-65ce53435ad9
• Taxonomy: Phenylpropanoids and polyketides > Aurone flavonoids > Auronols
• IUPAC Name: (2S)-2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-1-benzofuran-3-one
• SMILES (Canonical): C1=CC(=C(C=C1CC2(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@]2(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
• InChI: InChI=1S/C15H12O7/c16-8-4-11(19)13-12(5-8)22-15(21,14(13)20)6-7-1-2-9(17)10(18)3-7/h1-5,16-19,21H,6H2/t15-/m0/s1
• InChI Key: VCLACNNZBMRRES-HNNXBMFYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25 g/mol
• Exact Mass: 304.05830272 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.02
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7922	79.22%
Caco-2	-	0.7632	76.32%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5499	54.99%
OATP2B1 inhibitior	+	0.5670	56.70%
OATP1B1 inhibitior	+	0.9407	94.07%
OATP1B3 inhibitior	+	0.9109	91.09%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8030	80.30%
P-glycoprotein inhibitior	-	0.9499	94.99%
P-glycoprotein substrate	-	0.9341	93.41%
CYP3A4 substrate	-	0.5169	51.69%
CYP2C9 substrate	-	0.8036	80.36%
CYP2D6 substrate	-	0.8066	80.66%
CYP3A4 inhibition	-	0.6278	62.78%
CYP2C9 inhibition	-	0.8849	88.49%
CYP2C19 inhibition	-	0.8911	89.11%
CYP2D6 inhibition	-	0.8754	87.54%
CYP1A2 inhibition	-	0.8369	83.69%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.7833	78.33%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4802	48.02%
Eye corrosion	-	0.9922	99.22%
Eye irritation	+	0.9222	92.22%
Skin irritation	-	0.5811	58.11%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8391	83.91%
Micronuclear	+	0.7618	76.18%
Hepatotoxicity	-	0.5467	54.67%
skin sensitisation	-	0.7359	73.59%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6528	65.28%
Acute Oral Toxicity (c)	IV	0.3565	35.65%
Estrogen receptor binding	+	0.7650	76.50%
Androgen receptor binding	+	0.8028	80.28%
Thyroid receptor binding	+	0.5400	54.00%
Glucocorticoid receptor binding	+	0.7686	76.86%
Aromatase binding	+	0.7940	79.40%
PPAR gamma	+	0.6688	66.88%
Honey bee toxicity	-	0.7992	79.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9327	93.27%

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	99.26%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.56%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.45%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.41%	95.17%
CHEMBL4208	P20618	Proteasome component C5	88.64%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.19%	95.56%
CHEMBL3194	P02766	Transthyretin	86.20%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.88%	99.15%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.34%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.05%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.03%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.97%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.65%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	80.92%	94.73%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.87%	85.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.86%	86.33%

Plants that contains it

• Alphitonia excelsa

Cross-Links

• PubChem: 101534821
• LOTUS: LTS0222873
• wikiData: Q105283760