6,7,8-Trihydroxy-2-(4-methoxyphenyl)chromen-4-one

Details

• Internal ID: 6514ecd2-e36a-4a27-9205-5068e01b14ea
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: 6,7,8-trihydroxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=CC(=O)C3=CC(=C(C(=C3O2)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=CC(=O)C3=CC(=C(C(=C3O2)O)O)O
• InChI: InChI=1S/C16H12O6/c1-21-9-4-2-8(3-5-9)13-7-11(17)10-6-12(18)14(19)15(20)16(10)22-13/h2-7,18-20H,1H3
• InChI Key: YXKBIVMXBJYKCD-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26 g/mol
• Exact Mass: 300.06338810 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9095	90.95%
Caco-2	+	0.5159	51.59%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6297	62.97%
OATP2B1 inhibitior	-	0.6907	69.07%
OATP1B1 inhibitior	+	0.8972	89.72%
OATP1B3 inhibitior	+	0.9904	99.04%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7823	78.23%
P-glycoprotein inhibitior	-	0.8319	83.19%
P-glycoprotein substrate	-	0.9115	91.15%
CYP3A4 substrate	+	0.5199	51.99%
CYP2C9 substrate	-	0.8397	83.97%
CYP2D6 substrate	-	0.7876	78.76%
CYP3A4 inhibition	+	0.6330	63.30%
CYP2C9 inhibition	-	0.7982	79.82%
CYP2C19 inhibition	-	0.6361	63.61%
CYP2D6 inhibition	-	0.8687	86.87%
CYP1A2 inhibition	+	0.9091	90.91%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.7089	70.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6208	62.08%
Eye corrosion	-	0.9790	97.90%
Eye irritation	+	0.7302	73.02%
Skin irritation	-	0.6006	60.06%
Skin corrosion	-	0.9153	91.53%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6644	66.44%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6458	64.58%
skin sensitisation	-	0.9054	90.54%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8584	85.84%
Acute Oral Toxicity (c)	III	0.6309	63.09%
Estrogen receptor binding	+	0.9172	91.72%
Androgen receptor binding	+	0.9366	93.66%
Thyroid receptor binding	+	0.7161	71.61%
Glucocorticoid receptor binding	+	0.8959	89.59%
Aromatase binding	+	0.9287	92.87%
PPAR gamma	+	0.8364	83.64%
Honey bee toxicity	-	0.9306	93.06%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8562	85.62%

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	99.51%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.76%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	97.38%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.32%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.67%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.97%	98.95%
CHEMBL1907	P15144	Aminopeptidase N	88.78%	93.31%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.38%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.33%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.17%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.56%	86.92%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.16%	93.99%
CHEMBL3401	O75469	Pregnane X receptor	83.27%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.78%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.06%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.92%	95.89%

Plants that contains it

• Cistanche deserticola

Cross-Links

• PubChem: 16657777
• NPASS: NPC144233