5,6,2',6'-Tetrahydroxy-7,8-dimethoxyflavone

Details

• Internal ID: 91f5f634-7fd1-4484-b504-b6637e8d4764
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 2-(2,6-dihydroxyphenyl)-5,6-dihydroxy-7,8-dimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=O)C=C(OC2=C1OC)C3=C(C=CC=C3O)O)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=O)C=C(OC2=C1OC)C3=C(C=CC=C3O)O)O)O
• InChI: InChI=1S/C17H14O8/c1-23-16-14(22)13(21)12-9(20)6-10(25-15(12)17(16)24-2)11-7(18)4-3-5-8(11)19/h3-6,18-19,21-22H,1-2H3
• InChI Key: JJBOLVRIGHFVHG-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₈
• Molecular Weight: 346.30 g/mol
• Exact Mass: 346.06886740 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.30
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• LMPK12111427

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8965	89.65%
Caco-2	+	0.5424	54.24%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6457	64.57%
OATP2B1 inhibitior	-	0.5553	55.53%
OATP1B1 inhibitior	+	0.8977	89.77%
OATP1B3 inhibitior	+	0.9828	98.28%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8159	81.59%
P-glycoprotein inhibitior	+	0.6308	63.08%
P-glycoprotein substrate	-	0.8699	86.99%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.6887	68.87%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	+	0.6914	69.14%
CYP2C9 inhibition	-	0.8489	84.89%
CYP2C19 inhibition	-	0.6694	66.94%
CYP2D6 inhibition	-	0.8174	81.74%
CYP1A2 inhibition	+	0.8416	84.16%
CYP2C8 inhibition	+	0.5080	50.80%
CYP inhibitory promiscuity	+	0.6916	69.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6616	66.16%
Eye corrosion	-	0.9801	98.01%
Eye irritation	+	0.8367	83.67%
Skin irritation	-	0.6619	66.19%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5837	58.37%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.9068	90.68%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6886	68.86%
Acute Oral Toxicity (c)	III	0.5234	52.34%
Estrogen receptor binding	+	0.8342	83.42%
Androgen receptor binding	+	0.6649	66.49%
Thyroid receptor binding	+	0.6524	65.24%
Glucocorticoid receptor binding	+	0.8621	86.21%
Aromatase binding	+	0.6085	60.85%
PPAR gamma	+	0.7508	75.08%
Honey bee toxicity	-	0.8806	88.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8835	88.35%

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	98.86%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.09%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.60%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	94.10%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.01%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.76%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.52%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.81%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.26%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.65%	89.00%
CHEMBL2535	P11166	Glucose transporter	85.51%	98.75%
CHEMBL3194	P02766	Transthyretin	81.47%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.33%	99.17%

Plants that contains it

• Scutellaria prostrata

Cross-Links

• PubChem: 15101161
• LOTUS: LTS0105023
• wikiData: Q105129528