3,5,3'-Trihydroxy-6,7,8,4',5'-pentamethoxyflavone

Details

• Internal ID: 0b7b0ddd-afaf-43fa-8e5a-aa87dde59689
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 3,5-dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6,7,8-trimethoxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)O)C2=C(C(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)O)C2=C(C(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
• InChI: InChI=1S/C20H20O10/c1-25-10-7-8(6-9(21)16(10)26-2)15-14(24)12(22)11-13(23)18(27-3)20(29-5)19(28-4)17(11)30-15/h6-7,21,23-24H,1-5H3
• InChI Key: SBECGZQEVBSJHM-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₁₀
• Molecular Weight: 420.40 g/mol
• Exact Mass: 420.10564683 g/mol
• Topological Polar Surface Area (TPSA): 133.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 3,5,3'-Trihydroxy-6,7,8,4',5'-pentamethoxyflavone
• 3-O-demethyldigicitrin
• CHEMBL470678
• LMPK12113364

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	+	0.6873	68.73%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7936	79.36%
OATP2B1 inhibitior	-	0.7116	71.16%
OATP1B1 inhibitior	+	0.9197	91.97%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6332	63.32%
P-glycoprotein inhibitior	+	0.7404	74.04%
P-glycoprotein substrate	-	0.7961	79.61%
CYP3A4 substrate	+	0.5318	53.18%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.7237	72.37%
CYP2C9 inhibition	-	0.6863	68.63%
CYP2C19 inhibition	+	0.6566	65.66%
CYP2D6 inhibition	-	0.8329	83.29%
CYP1A2 inhibition	+	0.8642	86.42%
CYP2C8 inhibition	+	0.7364	73.64%
CYP inhibitory promiscuity	+	0.7231	72.31%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5851	58.51%
Eye corrosion	-	0.9825	98.25%
Eye irritation	-	0.6282	62.82%
Skin irritation	-	0.7275	72.75%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4263	42.63%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9511	95.11%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6227	62.27%
Acute Oral Toxicity (c)	III	0.4741	47.41%
Estrogen receptor binding	+	0.8415	84.15%
Androgen receptor binding	-	0.5057	50.57%
Thyroid receptor binding	+	0.6393	63.93%
Glucocorticoid receptor binding	+	0.7293	72.93%
Aromatase binding	+	0.7420	74.20%
PPAR gamma	+	0.6812	68.12%
Honey bee toxicity	-	0.8664	86.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5349	53.49%
Fish aquatic toxicity	+	0.8969	89.69%

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	98.47%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.60%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.33%	89.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	90.62%	98.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.52%	86.33%
CHEMBL2581	P07339	Cathepsin D	87.54%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.38%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.29%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.47%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.03%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.53%	99.23%
CHEMBL3194	P02766	Transthyretin	81.31%	90.71%

Plants that contains it

• Picrella trifoliata

Cross-Links

• PubChem: 44260075
• LOTUS: LTS0152142
• wikiData: Q105249348