5-Hydroxy-3,6,7,8-tetramethoxyflavone

Details

• Internal ID: 51b1b0bf-af18-4596-af0f-912a219dadc6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-3,6,7,8-tetramethoxy-2-phenylchromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1O)C(=O)C(=C(O2)C3=CC=CC=C3)OC)OC)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1O)C(=O)C(=C(O2)C3=CC=CC=C3)OC)OC)OC
• InChI: InChI=1S/C19H18O7/c1-22-16-12(20)11-13(21)17(23-2)19(25-4)18(24-3)15(11)26-14(16)10-8-6-5-7-9-10/h5-9,21H,1-4H3
• InChI Key: OIUOWUVXSYPYLM-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₇
• Molecular Weight: 358.30 g/mol
• Exact Mass: 358.10525291 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 15249-62-4
• 5-hydroxy-3,6,7,8-tetramethoxy-2-phenyl-4H-chromen-4-one
• SCHEMBL4129003
• CHEMBL2269545
• DTXSID70658072
• LMPK12113296
• 5-Hydroxy-3,6,7,8-tetramethoxy-2-phenyl-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9823	98.23%
Caco-2	+	0.6179	61.79%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7745	77.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9371	93.71%
OATP1B3 inhibitior	+	0.9817	98.17%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4694	46.94%
P-glycoprotein inhibitior	+	0.9016	90.16%
P-glycoprotein substrate	-	0.9179	91.79%
CYP3A4 substrate	-	0.5691	56.91%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.5748	57.48%
CYP2C9 inhibition	-	0.8861	88.61%
CYP2C19 inhibition	+	0.5778	57.78%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.8530	85.30%
CYP2C8 inhibition	+	0.5336	53.36%
CYP inhibitory promiscuity	+	0.6103	61.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5716	57.16%
Eye corrosion	-	0.9793	97.93%
Eye irritation	+	0.7161	71.61%
Skin irritation	-	0.7150	71.50%
Skin corrosion	-	0.9836	98.36%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5123	51.23%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.9504	95.04%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5050	50.50%
Acute Oral Toxicity (c)	II	0.4982	49.82%
Estrogen receptor binding	+	0.8049	80.49%
Androgen receptor binding	+	0.6575	65.75%
Thyroid receptor binding	+	0.7118	71.18%
Glucocorticoid receptor binding	+	0.7869	78.69%
Aromatase binding	+	0.6551	65.51%
PPAR gamma	+	0.7828	78.28%
Honey bee toxicity	-	0.9198	91.98%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8902	89.02%

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	98.62%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.18%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.17%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.06%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.03%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.54%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.98%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.67%	95.50%
CHEMBL3959	P16083	Quinone reductase 2	82.27%	89.49%
CHEMBL3401	O75469	Pregnane X receptor	81.82%	94.73%

Plants that contains it

• Durio carinatus
• Gamochaeta malvinensis
• Nothofagus pumilio
• Pseudognaphalium affine
• Pseudognaphalium cheiranthifolium
• Rubus idaeus
• Styrax formosanus

Cross-Links

• PubChem: 44260046
• NPASS: NPC292107
• LOTUS: LTS0158616
• wikiData: Q82573794