4',5,6-Trihydroxy-3',5',7-trimethoxyflavone

Details

• Internal ID: b5985188-73a9-44d6-a122-adc94c9e257d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5,6-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)O)O
• InChI: InChI=1S/C18H16O8/c1-23-12-4-8(5-13(24-2)16(12)20)10-6-9(19)15-11(26-10)7-14(25-3)17(21)18(15)22/h4-7,20-22H,1-3H3
• InChI Key: ZSWCONYQVQOSFZ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₈
• Molecular Weight: 360.30 g/mol
• Exact Mass: 360.08451746 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 4',5,6-Trihydroxy-3',5',7-trimethoxyflavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9464	94.64%
Caco-2	+	0.6242	62.42%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7784	77.84%
OATP2B1 inhibitior	-	0.5687	56.87%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	+	0.9791	97.91%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5508	55.08%
P-glycoprotein inhibitior	-	0.4788	47.88%
P-glycoprotein substrate	-	0.7580	75.80%
CYP3A4 substrate	-	0.5055	50.55%
CYP2C9 substrate	-	0.6887	68.87%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.7900	79.00%
CYP2C9 inhibition	-	0.8973	89.73%
CYP2C19 inhibition	-	0.7079	70.79%
CYP2D6 inhibition	-	0.9069	90.69%
CYP1A2 inhibition	+	0.8325	83.25%
CYP2C8 inhibition	+	0.5267	52.67%
CYP inhibitory promiscuity	+	0.5295	52.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9832	98.32%
Eye irritation	+	0.5935	59.35%
Skin irritation	-	0.7279	72.79%
Skin corrosion	-	0.9633	96.33%
Ames mutagenesis	-	0.6064	60.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.8232	82.32%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9405	94.05%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8039	80.39%
Acute Oral Toxicity (c)	II	0.4732	47.32%
Estrogen receptor binding	+	0.8842	88.42%
Androgen receptor binding	+	0.7797	77.97%
Thyroid receptor binding	+	0.6058	60.58%
Glucocorticoid receptor binding	+	0.8477	84.77%
Aromatase binding	+	0.7050	70.50%
PPAR gamma	+	0.7971	79.71%
Honey bee toxicity	-	0.7705	77.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.9122	91.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.75%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.21%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.65%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.60%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.91%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.82%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.87%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.42%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	82.67%	94.73%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.33%	94.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.96%	99.17%
CHEMBL3194	P02766	Transthyretin	81.73%	90.71%

Plants that contains it

• Lantana montevidensis
• Mulguraea tridens
• Pachylobus normandii
• Riccia fluitans

Cross-Links

• PubChem: 91602946
• NPASS: NPC274764
• LOTUS: LTS0116341
• wikiData: Q105382761