(2R,3R)-3-hydroxy-5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: 8e90a6fa-1897-4672-a36b-c9d6c341c8af
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: (2R,3R)-3-hydroxy-5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC)C(=O)C(C(O2)C3=CC=CC=C3)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)OC)C(=O)[C@@H]([C@H](O2)C3=CC=CC=C3)O
• InChI: InChI=1S/C17H16O5/c1-20-11-8-12(21-2)14-13(9-11)22-17(16(19)15(14)18)10-6-4-3-5-7-10/h3-9,16-17,19H,1-2H3/t16-,17+/m0/s1
• InChI Key: RAEBFGPECBAEAA-DLBZAZTESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.30 g/mol
• Exact Mass: 300.09977361 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9840	98.40%
Caco-2	+	0.6988	69.88%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7878	78.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9290	92.90%
OATP1B3 inhibitior	+	0.9891	98.91%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5163	51.63%
P-glycoprotein inhibitior	+	0.6549	65.49%
P-glycoprotein substrate	-	0.9549	95.49%
CYP3A4 substrate	-	0.5193	51.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6972	69.72%
CYP3A4 inhibition	+	0.6118	61.18%
CYP2C9 inhibition	+	0.5166	51.66%
CYP2C19 inhibition	+	0.8658	86.58%
CYP2D6 inhibition	-	0.8590	85.90%
CYP1A2 inhibition	+	0.8456	84.56%
CYP2C8 inhibition	-	0.5801	58.01%
CYP inhibitory promiscuity	+	0.6777	67.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5969	59.69%
Eye corrosion	-	0.9735	97.35%
Eye irritation	+	0.6223	62.23%
Skin irritation	-	0.6296	62.96%
Skin corrosion	-	0.9794	97.94%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5431	54.31%
Micronuclear	+	0.8959	89.59%
Hepatotoxicity	+	0.6034	60.34%
skin sensitisation	-	0.9380	93.80%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6834	68.34%
Acute Oral Toxicity (c)	III	0.5284	52.84%
Estrogen receptor binding	+	0.7149	71.49%
Androgen receptor binding	+	0.6014	60.14%
Thyroid receptor binding	+	0.6449	64.49%
Glucocorticoid receptor binding	+	0.6790	67.90%
Aromatase binding	-	0.4863	48.63%
PPAR gamma	+	0.6723	67.23%
Honey bee toxicity	-	0.8936	89.36%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.8830	88.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.65%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.90%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.22%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.53%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.71%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	91.44%	83.82%
CHEMBL2581	P07339	Cathepsin D	86.77%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.42%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.85%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.31%	95.50%
CHEMBL2535	P11166	Glucose transporter	81.04%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.75%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.29%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	80.25%	94.73%

Plants that contains it

• Aniba riparia

Cross-Links

• PubChem: 15698021
• LOTUS: LTS0035043
• wikiData: Q105232550