5,8-Dihydroxy-3,7-dimethoxyflavone

Details

• Internal ID: 286847ae-db17-4752-96bb-f137e84537c6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5,8-dihydroxy-3,7-dimethoxy-2-phenylchromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C(=C1)O)C(=O)C(=C(O2)C3=CC=CC=C3)OC)O
• SMILES (Isomeric): COC1=C(C2=C(C(=C1)O)C(=O)C(=C(O2)C3=CC=CC=C3)OC)O
• InChI: InChI=1S/C17H14O6/c1-21-11-8-10(18)12-14(20)17(22-2)15(23-16(12)13(11)19)9-6-4-3-5-7-9/h3-8,18-19H,1-2H3
• InChI Key: FIERIMLAOJMXIK-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.29 g/mol
• Exact Mass: 314.07903816 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 5,8-Dihydroxy-3,7-dimethoxyflavone
• 33803-31-5
• LMPK12113092

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9730	97.30%
Caco-2	-	0.5142	51.42%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8156	81.56%
OATP2B1 inhibitior	-	0.7172	71.72%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9738	97.38%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5782	57.82%
P-glycoprotein inhibitior	+	0.8089	80.89%
P-glycoprotein substrate	-	0.8718	87.18%
CYP3A4 substrate	-	0.5250	52.50%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.5571	55.71%
CYP2C9 inhibition	+	0.7766	77.66%
CYP2C19 inhibition	+	0.8962	89.62%
CYP2D6 inhibition	-	0.7334	73.34%
CYP1A2 inhibition	+	0.8679	86.79%
CYP2C8 inhibition	+	0.6894	68.94%
CYP inhibitory promiscuity	+	0.7750	77.50%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.9782	97.82%
Eye irritation	+	0.6595	65.95%
Skin irritation	-	0.6511	65.11%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	+	0.5063	50.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6350	63.50%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.9410	94.10%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6330	63.30%
Acute Oral Toxicity (c)	III	0.5602	56.02%
Estrogen receptor binding	+	0.7812	78.12%
Androgen receptor binding	+	0.7522	75.22%
Thyroid receptor binding	+	0.5669	56.69%
Glucocorticoid receptor binding	+	0.8356	83.56%
Aromatase binding	+	0.8079	80.79%
PPAR gamma	+	0.8264	82.64%
Honey bee toxicity	-	0.8936	89.36%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5251	52.51%
Fish aquatic toxicity	+	0.8898	88.98%

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	99.36%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.85%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.43%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.81%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.04%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.99%	89.00%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	89.16%	98.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.60%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.76%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.34%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.50%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	82.07%	90.20%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.62%	85.14%

Plants that contains it

• Achyrocline flaccida
• Carthamus arborescens
• Cephalotaxus fortunei
• Nothofagus solandri

Cross-Links

• PubChem: 44259913
• NPASS: NPC218465
• LOTUS: LTS0075555
• wikiData: Q104995670