5,7-Dihydroxy-6,8,2',3'-tetramethoxyflavone

Details

• Internal ID: caf249be-a807-4f34-ac9e-3d31e471db39
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 2-(2,3-dimethoxyphenyl)-5,7-dihydroxy-6,8-dimethoxychromen-4-one
• SMILES (Canonical): COC1=CC=CC(=C1OC)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)O)OC)O
• SMILES (Isomeric): COC1=CC=CC(=C1OC)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)O)OC)O
• InChI: InChI=1S/C19H18O8/c1-23-11-7-5-6-9(16(11)24-2)12-8-10(20)13-14(21)18(25-3)15(22)19(26-4)17(13)27-12/h5-8,21-22H,1-4H3
• InChI Key: DSNICWRJCXGVEE-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.10016753 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9417	94.17%
Caco-2	+	0.7174	71.74%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.8579	85.79%
OATP1B3 inhibitior	+	0.8767	87.67%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5712	57.12%
P-glycoprotein inhibitior	+	0.7670	76.70%
P-glycoprotein substrate	-	0.6284	62.84%
CYP3A4 substrate	+	0.5605	56.05%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.6154	61.54%
CYP2C9 inhibition	-	0.7484	74.84%
CYP2C19 inhibition	+	0.5640	56.40%
CYP2D6 inhibition	-	0.7310	73.10%
CYP1A2 inhibition	+	0.8610	86.10%
CYP2C8 inhibition	+	0.5742	57.42%
CYP inhibitory promiscuity	+	0.8068	80.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6142	61.42%
Eye corrosion	-	0.9818	98.18%
Eye irritation	+	0.6582	65.82%
Skin irritation	-	0.7187	71.87%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7062	70.62%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.9352	93.52%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6065	60.65%
Acute Oral Toxicity (c)	III	0.5210	52.10%
Estrogen receptor binding	+	0.8850	88.50%
Androgen receptor binding	+	0.7461	74.61%
Thyroid receptor binding	+	0.6951	69.51%
Glucocorticoid receptor binding	+	0.7832	78.32%
Aromatase binding	+	0.6742	67.42%
PPAR gamma	+	0.7640	76.40%
Honey bee toxicity	-	0.8802	88.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8724	87.24%

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	97.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.97%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.08%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.85%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.42%	86.33%
CHEMBL2535	P11166	Glucose transporter	92.16%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.06%	89.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.32%	94.03%
CHEMBL1255126	O15151	Protein Mdm4	85.28%	90.20%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.45%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.40%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.81%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.99%	99.23%
CHEMBL3194	P02766	Transthyretin	82.78%	90.71%
CHEMBL1907	P15144	Aminopeptidase N	81.40%	93.31%

Plants that contains it

• Artemisia annua
• Scutellaria baicalensis

Cross-Links

• PubChem: 5316833
• NPASS: NPC158151