(2R,3S)-4'-O-methyl-2,3-dihydromyricetin

Details

• Internal ID: f8e9bb20-5507-43a0-9956-2fd1ed965e53
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Epigallocatechins
• IUPAC Name: (2R,3S)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1O)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1O)[C@@H]2[C@@H](C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• InChI: InChI=1S/C16H14O8/c1-23-16-9(19)2-6(3-10(16)20)15-14(22)13(21)12-8(18)4-7(17)5-11(12)24-15/h2-5,14-15,17-20,22H,1H3/t14-,15-/m1/s1
• InChI Key: NKPORGOKKIBGPG-HUUCEWRRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₈
• Molecular Weight: 334.28 g/mol
• Exact Mass: 334.06886740 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• (2R,3S)-4'-O-methyl-2,3-dihydromyricetin

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9524	95.24%
Caco-2	-	0.6648	66.48%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6494	64.94%
OATP2B1 inhibitior	-	0.6962	69.62%
OATP1B1 inhibitior	+	0.9349	93.49%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9121	91.21%
P-glycoprotein inhibitior	-	0.8503	85.03%
P-glycoprotein substrate	-	0.9500	95.00%
CYP3A4 substrate	+	0.5275	52.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7873	78.73%
CYP3A4 inhibition	+	0.7348	73.48%
CYP2C9 inhibition	+	0.7560	75.60%
CYP2C19 inhibition	+	0.8648	86.48%
CYP2D6 inhibition	-	0.6993	69.93%
CYP1A2 inhibition	+	0.9218	92.18%
CYP2C8 inhibition	-	0.6451	64.51%
CYP inhibitory promiscuity	+	0.8546	85.46%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6176	61.76%
Eye corrosion	-	0.9767	97.67%
Eye irritation	+	0.8503	85.03%
Skin irritation	-	0.5841	58.41%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5882	58.82%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.9240	92.40%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5900	59.00%
Acute Oral Toxicity (c)	III	0.7362	73.62%
Estrogen receptor binding	+	0.7301	73.01%
Androgen receptor binding	-	0.5521	55.21%
Thyroid receptor binding	+	0.7044	70.44%
Glucocorticoid receptor binding	+	0.6733	67.33%
Aromatase binding	+	0.5199	51.99%
PPAR gamma	+	0.6678	66.78%
Honey bee toxicity	-	0.8635	86.35%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8321	83.21%

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	97.85%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.74%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.89%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.76%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.96%	86.33%
CHEMBL2581	P07339	Cathepsin D	86.73%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.40%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.76%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	85.33%	94.73%
CHEMBL2535	P11166	Glucose transporter	84.63%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.94%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.81%	99.17%

Plants that contains it

• Gymnosporia senegalensis
• Maytenus laevis

Cross-Links

• PubChem: 11244528
• NPASS: NPC250922
• LOTUS: LTS0216979
• wikiData: Q105180713