3,5,7-Trihydroxy-8-methoxyflavone

Details

• Internal ID: 1ebb9598-3d6b-4c8f-ba9c-0e0cfe0767c9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 3,5,7-trihydroxy-8-methoxy-2-phenylchromen-4-one
• SMILES (Canonical): COC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=CC=C3)O)O
• SMILES (Isomeric): COC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=CC=C3)O)O
• InChI: InChI=1S/C16H12O6/c1-21-15-10(18)7-9(17)11-12(19)13(20)14(22-16(11)15)8-5-3-2-4-6-8/h2-7,17-18,20H,1H3
• InChI Key: NAENHANDGVDMPA-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26 g/mol
• Exact Mass: 300.06338810 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 8-Methoxygalangin
• NAENHANDGVDMPA-UHFFFAOYSA-N
• 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-8-methoxy-2-phenyl-
• LMPK12113091
• AKOS040762719
• 3,5,7-Trihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one #
• (4H)1-Benzopyran-4-one, 3,5,7-trihydroxy-8-methoxy-2-phenyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9524	95.24%
Caco-2	-	0.5347	53.47%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6494	64.94%
OATP2B1 inhibitior	-	0.6914	69.14%
OATP1B1 inhibitior	+	0.9328	93.28%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5418	54.18%
P-glycoprotein inhibitior	-	0.4387	43.87%
P-glycoprotein substrate	-	0.8624	86.24%
CYP3A4 substrate	-	0.5368	53.68%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.7348	73.48%
CYP2C9 inhibition	+	0.7560	75.60%
CYP2C19 inhibition	+	0.8648	86.48%
CYP2D6 inhibition	-	0.6993	69.93%
CYP1A2 inhibition	+	0.9218	92.18%
CYP2C8 inhibition	+	0.5737	57.37%
CYP inhibitory promiscuity	+	0.8546	85.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6176	61.76%
Eye corrosion	-	0.9767	97.67%
Eye irritation	+	0.7974	79.74%
Skin irritation	-	0.5841	58.41%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6887	68.87%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9240	92.40%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7471	74.71%
Acute Oral Toxicity (c)	III	0.7362	73.62%
Estrogen receptor binding	+	0.8602	86.02%
Androgen receptor binding	+	0.7082	70.82%
Thyroid receptor binding	+	0.6789	67.89%
Glucocorticoid receptor binding	+	0.8854	88.54%
Aromatase binding	+	0.7771	77.71%
PPAR gamma	+	0.8081	80.81%
Honey bee toxicity	-	0.9103	91.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8321	83.21%

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	99.45%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.49%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.63%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.52%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.88%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.46%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.78%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.65%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.25%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	84.34%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.17%	99.17%

Plants that contains it

• Adenostoma sparsifolium
• Helichrysum italicum
• Muntingia calabura
• Nothofagus antarctica
• Woodsia scopulina

Cross-Links

• PubChem: 5378234
• LOTUS: LTS0070979
• wikiData: Q104375662