5,8-Dihydroxy-7-methoxyflavanone

Details

• Internal ID: f589dccc-af2b-452e-99e8-f45b62b8ea65
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5,8-dihydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C(=O)CC(O2)C3=CC=CC=C3)C(=C1)O)O
• SMILES (Isomeric): COC1=C(C2=C(C(=O)CC(O2)C3=CC=CC=C3)C(=C1)O)O
• InChI: InChI=1S/C16H14O5/c1-20-13-8-11(18)14-10(17)7-12(21-16(14)15(13)19)9-5-3-2-4-6-9/h2-6,8,12,18-19H,7H2,1H3
• InChI Key: AIUFGSSCCIXONA-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• SCHEMBL17907266
• CHEBI:178312
• LMPK12140663
• 5,8-dihydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9548	95.48%
Caco-2	+	0.5724	57.24%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8104	81.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9099	90.99%
OATP1B3 inhibitior	+	0.9893	98.93%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7775	77.75%
P-glycoprotein inhibitior	-	0.7269	72.69%
P-glycoprotein substrate	-	0.9247	92.47%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	-	0.5998	59.98%
CYP2C9 inhibition	+	0.9418	94.18%
CYP2C19 inhibition	+	0.9415	94.15%
CYP2D6 inhibition	-	0.5079	50.79%
CYP1A2 inhibition	+	0.9148	91.48%
CYP2C8 inhibition	+	0.5225	52.25%
CYP inhibitory promiscuity	+	0.7165	71.65%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5242	52.42%
Eye corrosion	-	0.9851	98.51%
Eye irritation	+	0.6095	60.95%
Skin irritation	-	0.6425	64.25%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7342	73.42%
Micronuclear	+	0.8559	85.59%
Hepatotoxicity	-	0.5218	52.18%
skin sensitisation	-	0.9411	94.11%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.5591	55.91%
Acute Oral Toxicity (c)	III	0.5701	57.01%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5541	55.41%
Thyroid receptor binding	-	0.5855	58.55%
Glucocorticoid receptor binding	+	0.7241	72.41%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7063	70.63%
Honey bee toxicity	-	0.8565	85.65%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.7667	76.67%

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	98.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.01%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.27%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.62%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.98%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.72%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.47%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.08%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.64%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.37%	99.15%
CHEMBL2535	P11166	Glucose transporter	81.80%	98.75%
CHEMBL4208	P20618	Proteasome component C5	80.81%	90.00%

Plants that contains it

• Helichrysum cymosum

Cross-Links

• PubChem: 13888646
• LOTUS: LTS0118144
• wikiData: Q104912972