(2S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

Details

• Internal ID: b02f9654-c83f-44dc-a8f1-e66a27b85233
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: (2S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
• SMILES (Isomeric): C1C([C@@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
• InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13?,15-/m0/s1
• InChI Key: PFTAWBLQPZVEMU-WUJWULDRSA-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): 110.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• SCHEMBL13610161

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8922	89.22%
Caco-2	-	0.9406	94.06%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4440	44.40%
OATP2B1 inhibitior	-	0.5776	57.76%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9228	92.28%
P-glycoprotein inhibitior	-	0.9411	94.11%
P-glycoprotein substrate	-	0.9531	95.31%
CYP3A4 substrate	-	0.5560	55.60%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	+	0.5322	53.22%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9041	90.41%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.4599	45.99%
CYP inhibitory promiscuity	-	0.8170	81.70%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5825	58.25%
Eye corrosion	-	0.9901	99.01%
Eye irritation	+	0.9629	96.29%
Skin irritation	-	0.5859	58.59%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4678	46.78%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.7452	74.52%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6369	63.69%
Acute Oral Toxicity (c)	IV	0.6433	64.33%
Estrogen receptor binding	-	0.6719	67.19%
Androgen receptor binding	+	0.6638	66.38%
Thyroid receptor binding	+	0.7658	76.58%
Glucocorticoid receptor binding	+	0.6993	69.93%
Aromatase binding	+	0.6008	60.08%
PPAR gamma	+	0.6832	68.32%
Honey bee toxicity	-	0.8419	84.19%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.7342	73.42%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5979	P05186	Alkaline phosphatase, tissue-nonspecific isozyme	407 nM	IC50	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	450 nM	Ki	via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	28.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.36%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.34%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.87%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.65%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.55%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.27%	95.56%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.19%	96.12%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.40%	93.40%
CHEMBL3194	P02766	Transthyretin	84.35%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	81.47%	94.73%
CHEMBL3438	Q05513	Protein kinase C zeta	81.02%	88.48%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.01%	94.45%
CHEMBL4208	P20618	Proteasome component C5	80.01%	90.00%

Plants that contains it

• Reynoutria multiflora

Cross-Links

• PubChem: 12309507
• NPASS: NPC111440