2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,6,8-triol

Details

• Internal ID: b07e52c2-5431-46d4-87e1-11ee9dba011b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavan-3-ols
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,6,8-triol
• SMILES (Canonical): C1C(C(OC2=C1C=C(C=C2O)O)C3=CC(=C(C=C3)O)O)O
• SMILES (Isomeric): C1C(C(OC2=C1C=C(C=C2O)O)C3=CC(=C(C=C3)O)O)O
• InChI: InChI=1S/C15H14O6/c16-9-3-8-5-12(19)14(21-15(8)13(20)6-9)7-1-2-10(17)11(18)4-7/h1-4,6,12,14,16-20H,5H2
• InChI Key: ADRVNXBAWSRFAJ-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): 110.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 6
• 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	+	0.7965	79.65%
Caco-2	-	0.7039	70.39%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4339	43.39%
OATP2B1 inhibitior	-	0.5760	57.60%
OATP1B1 inhibitior	+	0.9478	94.78%
OATP1B3 inhibitior	+	0.9839	98.39%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9385	93.85%
P-glycoprotein inhibitior	-	0.9438	94.38%
P-glycoprotein substrate	-	0.9339	93.39%
CYP3A4 substrate	+	0.5061	50.61%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	+	0.5322	53.22%
CYP3A4 inhibition	-	0.6346	63.46%
CYP2C9 inhibition	-	0.7051	70.51%
CYP2C19 inhibition	-	0.8571	85.71%
CYP2D6 inhibition	-	0.7700	77.00%
CYP1A2 inhibition	-	0.6448	64.48%
CYP2C8 inhibition	-	0.6367	63.67%
CYP inhibitory promiscuity	-	0.6759	67.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5510	55.10%
Eye corrosion	-	0.9920	99.20%
Eye irritation	+	0.8742	87.42%
Skin irritation	-	0.5736	57.36%
Skin corrosion	-	0.9101	91.01%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6053	60.53%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7737	77.37%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7816	78.16%
Acute Oral Toxicity (c)	IV	0.4396	43.96%
Estrogen receptor binding	-	0.6449	64.49%
Androgen receptor binding	+	0.6332	63.32%
Thyroid receptor binding	+	0.6594	65.94%
Glucocorticoid receptor binding	+	0.6674	66.74%
Aromatase binding	+	0.5432	54.32%
PPAR gamma	+	0.5774	57.74%
Honey bee toxicity	-	0.8517	85.17%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.7271	72.71%

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	99.05%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.73%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.28%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.02%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	90.63%	94.73%
CHEMBL233	P35372	Mu opioid receptor	90.09%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.41%	95.56%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.90%	96.12%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.33%	99.15%
CHEMBL2581	P07339	Cathepsin D	82.70%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.19%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	82.16%	95.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.37%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.29%	86.33%
CHEMBL3194	P02766	Transthyretin	80.26%	90.71%

Plants that contains it

• Fagopyrum esculentum
• Leucaena leucocephala

Cross-Links

• PubChem: 163015940
• LOTUS: LTS0257019
• wikiData: Q104909767