5-[3-(3-Hydroxy-4-methoxyphenyl)oxiran-2-yl]benzene-1,2,3-triol

Details

• Internal ID: 10727593-1ea6-4fba-9d60-8699065bb390
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[3-(3-hydroxy-4-methoxyphenyl)oxiran-2-yl]benzene-1,2,3-triol
• SMILES (Canonical): COC1=C(C=C(C=C1)C2C(O2)C3=CC(=C(C(=C3)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2C(O2)C3=CC(=C(C(=C3)O)O)O)O
• InChI: InChI=1S/C15H14O6/c1-20-12-3-2-7(4-9(12)16)14-15(21-14)8-5-10(17)13(19)11(18)6-8/h2-6,14-19H,1H3
• InChI Key: QEBJRFCJPQJNBI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₆
• Molecular Weight: 290.27 g/mol
• Exact Mass: 290.07903816 g/mol
• Topological Polar Surface Area (TPSA): 103.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8704	87.04%
Caco-2	-	0.5698	56.98%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6311	63.11%
OATP2B1 inhibitior	-	0.7190	71.90%
OATP1B1 inhibitior	+	0.9159	91.59%
OATP1B3 inhibitior	+	0.9737	97.37%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8936	89.36%
P-glycoprotein inhibitior	-	0.9428	94.28%
P-glycoprotein substrate	-	0.9557	95.57%
CYP3A4 substrate	-	0.5721	57.21%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.6826	68.26%
CYP3A4 inhibition	-	0.6673	66.73%
CYP2C9 inhibition	-	0.6786	67.86%
CYP2C19 inhibition	-	0.5625	56.25%
CYP2D6 inhibition	-	0.9003	90.03%
CYP1A2 inhibition	+	0.5228	52.28%
CYP2C8 inhibition	+	0.5911	59.11%
CYP inhibitory promiscuity	+	0.7804	78.04%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5371	53.71%
Eye corrosion	-	0.9791	97.91%
Eye irritation	+	0.7624	76.24%
Skin irritation	-	0.6591	65.91%
Skin corrosion	-	0.8289	82.89%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5523	55.23%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7560	75.60%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7678	76.78%
Acute Oral Toxicity (c)	III	0.6458	64.58%
Estrogen receptor binding	+	0.5767	57.67%
Androgen receptor binding	+	0.6586	65.86%
Thyroid receptor binding	+	0.7148	71.48%
Glucocorticoid receptor binding	+	0.5835	58.35%
Aromatase binding	+	0.6471	64.71%
PPAR gamma	+	0.7225	72.25%
Honey bee toxicity	-	0.9634	96.34%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5551	55.51%
Fish aquatic toxicity	+	0.8864	88.64%

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	98.35%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.61%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.93%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.62%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.63%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.94%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.70%	94.73%
CHEMBL3194	P02766	Transthyretin	86.45%	90.71%
CHEMBL3438	Q05513	Protein kinase C zeta	85.68%	88.48%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.46%	85.14%
CHEMBL4208	P20618	Proteasome component C5	82.01%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.78%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.61%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.15%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.10%	99.15%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.06%	92.62%

Plants that contains it

• Gnetum montanum

Cross-Links

• PubChem: 163031571
• LOTUS: LTS0091446
• wikiData: Q105219111