(2R,3R)-3,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-5-olate

Details

• Internal ID: 18e4dad5-c0c5-4a01-b4be-7a09ed097df2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Epigallocatechins
• IUPAC Name: (2R,3R)-3,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-5-olate
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C2C(C(=O)C3=C(C=C(C=C3O2)O)[O-])O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)[O-])O
• InChI: InChI=1S/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/p-1/t14-,15+/m0/s1
• InChI Key: KJXSIXMJHKAJOD-LSDHHAIUSA-M
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₁O₈-
• Molecular Weight: 319.24 g/mol
• Exact Mass: 319.04539230 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.26
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7618	76.18%
Caco-2	-	0.9553	95.53%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4686	46.86%
OATP2B1 inhibitior	-	0.5536	55.36%
OATP1B1 inhibitior	+	0.8901	89.01%
OATP1B3 inhibitior	+	0.9316	93.16%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8964	89.64%
P-glycoprotein inhibitior	-	0.8898	88.98%
P-glycoprotein substrate	-	0.9398	93.98%
CYP3A4 substrate	-	0.5219	52.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8066	80.66%
CYP3A4 inhibition	+	0.6432	64.32%
CYP2C9 inhibition	-	0.6339	63.39%
CYP2C19 inhibition	-	0.8892	88.92%
CYP2D6 inhibition	-	0.9159	91.59%
CYP1A2 inhibition	+	0.8760	87.60%
CYP2C8 inhibition	-	0.6169	61.69%
CYP inhibitory promiscuity	-	0.5084	50.84%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6676	66.76%
Eye corrosion	-	0.9894	98.94%
Eye irritation	+	0.9696	96.96%
Skin irritation	+	0.5380	53.80%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6789	67.89%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.7725	77.25%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5721	57.21%
Acute Oral Toxicity (c)	II	0.6824	68.24%
Estrogen receptor binding	+	0.6761	67.61%
Androgen receptor binding	+	0.6805	68.05%
Thyroid receptor binding	+	0.6998	69.98%
Glucocorticoid receptor binding	+	0.7532	75.32%
Aromatase binding	+	0.6217	62.17%
PPAR gamma	+	0.7033	70.33%
Honey bee toxicity	-	0.8934	89.34%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9121	91.21%

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	98.71%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.24%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.70%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.87%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.54%	94.45%
CHEMBL3194	P02766	Transthyretin	86.65%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	84.72%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.04%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.34%	86.33%
CHEMBL2581	P07339	Cathepsin D	80.88%	98.95%

Plants that contains it

• Ampelopsis japonica
• Nekemias grossedentata

Cross-Links

• PubChem: 25244375
• NPASS: NPC19724