(2R,3R)-3,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydrochromen-4-one

Details

• Internal ID: e3a32d3b-d3cd-4e94-89ef-7b8f5bb01802
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
• IUPAC Name: (2R,3R)-3,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C(C(=O)C3=C(O2)C=C(C=C3)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H](C(=O)C3=C(O2)C=C(C=C3)O)O
• InChI: InChI=1S/C17H16O7/c1-22-12-5-8(6-13(23-2)15(12)20)17-16(21)14(19)10-4-3-9(18)7-11(10)24-17/h3-7,16-18,20-21H,1-2H3/t16-,17+/m0/s1
• InChI Key: JDEBLAIUKXAQFI-DLBZAZTESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₇
• Molecular Weight: 332.30 g/mol
• Exact Mass: 332.08960285 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9730	97.30%
Caco-2	-	0.5441	54.41%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8156	81.56%
OATP2B1 inhibitior	-	0.7124	71.24%
OATP1B1 inhibitior	+	0.7977	79.77%
OATP1B3 inhibitior	+	0.9738	97.38%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6820	68.20%
P-glycoprotein inhibitior	-	0.5250	52.50%
P-glycoprotein substrate	-	0.7694	76.94%
CYP3A4 substrate	+	0.5666	56.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7112	71.12%
CYP3A4 inhibition	-	0.5571	55.71%
CYP2C9 inhibition	+	0.7766	77.66%
CYP2C19 inhibition	+	0.8962	89.62%
CYP2D6 inhibition	-	0.7334	73.34%
CYP1A2 inhibition	+	0.8679	86.79%
CYP2C8 inhibition	+	0.5257	52.57%
CYP inhibitory promiscuity	+	0.7750	77.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.9782	97.82%
Eye irritation	+	0.7680	76.80%
Skin irritation	-	0.6511	65.11%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8320	83.20%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.9410	94.10%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5602	56.02%
Estrogen receptor binding	+	0.7697	76.97%
Androgen receptor binding	-	0.5128	51.28%
Thyroid receptor binding	+	0.6960	69.60%
Glucocorticoid receptor binding	+	0.7070	70.70%
Aromatase binding	-	0.5253	52.53%
PPAR gamma	+	0.6572	65.72%
Honey bee toxicity	-	0.8763	87.63%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8898	88.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.91%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.59%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.57%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.24%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.71%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.86%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.65%	94.00%
CHEMBL2535	P11166	Glucose transporter	86.34%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.70%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.58%	95.89%
CHEMBL3194	P02766	Transthyretin	80.39%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.34%	99.23%

Plants that contains it

• Sophora yunnanensis

Cross-Links

• PubChem: 56834824
• LOTUS: LTS0084179
• wikiData: Q105125399