4-[(2R)-8-(2-hydroxyethyl)-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzene-1,3-diol

Details

• Internal ID: 5a63f140-1e4b-42be-8883-c633bbba8a99
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 4-[(2R)-8-(2-hydroxyethyl)-7-methoxy-3,4-dihydro-2H-chromen-2-yl]benzene-1,3-diol
• SMILES (Canonical): COC1=C(C2=C(CCC(O2)C3=C(C=C(C=C3)O)O)C=C1)CCO
• SMILES (Isomeric): COC1=C(C2=C(CC[C@@H](O2)C3=C(C=C(C=C3)O)O)C=C1)CCO
• InChI: InChI=1S/C18H20O5/c1-22-16-6-2-11-3-7-17(23-18(11)14(16)8-9-19)13-5-4-12(20)10-15(13)21/h2,4-6,10,17,19-21H,3,7-9H2,1H3/t17-/m1/s1
• InChI Key: BJVDGVPUXJNXHR-QGZVFWFLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.13107373 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.71
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• BDBM50364139
• (2R)-3,4-Dihydro-7-methoxy-2-(2,4-dihydroxyphenyl)-8-(2-hydroxyethyl)-2H-1-benzopyran

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8736	87.36%
Caco-2	+	0.8298	82.98%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7630	76.30%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.8637	86.37%
OATP1B3 inhibitior	+	0.9365	93.65%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5296	52.96%
P-glycoprotein inhibitior	-	0.7412	74.12%
P-glycoprotein substrate	+	0.5905	59.05%
CYP3A4 substrate	+	0.6535	65.35%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	+	0.5279	52.79%
CYP3A4 inhibition	+	0.6194	61.94%
CYP2C9 inhibition	-	0.6779	67.79%
CYP2C19 inhibition	-	0.5449	54.49%
CYP2D6 inhibition	-	0.8144	81.44%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.7781	77.81%
CYP inhibitory promiscuity	+	0.6961	69.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7157	71.57%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.6329	63.29%
Skin irritation	-	0.7850	78.50%
Skin corrosion	-	0.9472	94.72%
Ames mutagenesis	-	0.7540	75.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.4613	46.13%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8600	86.00%
Acute Oral Toxicity (c)	III	0.5608	56.08%
Estrogen receptor binding	+	0.8180	81.80%
Androgen receptor binding	+	0.7546	75.46%
Thyroid receptor binding	+	0.6765	67.65%
Glucocorticoid receptor binding	+	0.6881	68.81%
Aromatase binding	-	0.5322	53.22%
PPAR gamma	+	0.6202	62.02%
Honey bee toxicity	-	0.8454	84.54%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.20%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.70%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.38%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.61%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.56%	95.89%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.09%	91.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.42%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.99%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.42%	95.56%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.54%	89.05%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.23%	92.94%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.11%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.10%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.66%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.02%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.94%	92.62%
CHEMBL4040	P28482	MAP kinase ERK2	85.84%	83.82%
CHEMBL2535	P11166	Glucose transporter	85.48%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.62%	89.62%
CHEMBL5555	O00767	Acyl-CoA desaturase	84.61%	97.50%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.32%	96.39%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.16%	94.03%
CHEMBL217	P14416	Dopamine D2 receptor	81.92%	95.62%
CHEMBL4581	P52732	Kinesin-like protein 1	81.27%	93.18%

Plants that contains it

• Morus notabilis
• Rosa rugosa

Cross-Links

• PubChem: 53468592
• NPASS: NPC274717
• ChEMBL: CHEMBL1951301
• LOTUS: LTS0266223
• wikiData: Q104937377