(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-ethoxy-3,4-dihydro-2H-chromene-3,7,8-triol

Details

• Internal ID: 93b72c69-6adc-4816-8164-4f1d26bf9422
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Leucoanthocyanidins
• IUPAC Name: (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-ethoxy-3,4-dihydro-2H-chromene-3,7,8-triol
• SMILES (Canonical): CCOC1C(C(OC2=C1C=CC(=C2O)O)C3=CC(=C(C=C3)O)O)O
• SMILES (Isomeric): CCO[C@@H]1[C@H]([C@H](OC2=C1C=CC(=C2O)O)C3=CC(=C(C=C3)O)O)O
• InChI: InChI=1S/C17H18O7/c1-2-23-16-9-4-6-11(19)13(21)17(9)24-15(14(16)22)8-3-5-10(18)12(20)7-8/h3-7,14-16,18-22H,2H2,1H3/t14-,15+,16-/m0/s1
• InChI Key: NQOFTXRHCNWFGZ-XHSDSOJGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₇
• Molecular Weight: 334.30 g/mol
• Exact Mass: 334.10525291 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8791	87.91%
Caco-2	-	0.8070	80.70%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7926	79.26%
OATP2B1 inhibitior	-	0.5717	57.17%
OATP1B1 inhibitior	+	0.9127	91.27%
OATP1B3 inhibitior	+	0.9713	97.13%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7631	76.31%
P-glycoprotein inhibitior	-	0.8043	80.43%
P-glycoprotein substrate	-	0.8628	86.28%
CYP3A4 substrate	+	0.5448	54.48%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	+	0.3969	39.69%
CYP3A4 inhibition	-	0.8928	89.28%
CYP2C9 inhibition	+	0.8625	86.25%
CYP2C19 inhibition	+	0.7812	78.12%
CYP2D6 inhibition	-	0.8825	88.25%
CYP1A2 inhibition	+	0.7929	79.29%
CYP2C8 inhibition	+	0.5866	58.66%
CYP inhibitory promiscuity	+	0.8303	83.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5808	58.08%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.4872	48.72%
Skin irritation	-	0.7639	76.39%
Skin corrosion	-	0.9528	95.28%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3933	39.33%
Micronuclear	+	0.7259	72.59%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9034	90.34%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7467	74.67%
Acute Oral Toxicity (c)	III	0.6468	64.68%
Estrogen receptor binding	+	0.6365	63.65%
Androgen receptor binding	+	0.6521	65.21%
Thyroid receptor binding	+	0.6480	64.80%
Glucocorticoid receptor binding	+	0.7327	73.27%
Aromatase binding	+	0.5632	56.32%
PPAR gamma	+	0.5174	51.74%
Honey bee toxicity	-	0.8655	86.55%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6050	60.50%
Fish aquatic toxicity	+	0.9329	93.29%

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	98.50%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.09%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.65%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.74%	94.73%
CHEMBL2581	P07339	Cathepsin D	89.58%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.27%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.96%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.19%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.95%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.01%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.24%	99.17%

Plants that contains it

• Acacia melanoxylon

Cross-Links

• PubChem: 21676334
• LOTUS: LTS0247096
• wikiData: Q105184007