5,6,7-Trimethoxy-8-hydroxy-2H-1-benzopyran-2-one

Details

• Internal ID: dcc9c049-3422-4901-bd0b-d1f9d60fb1cb
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins
• IUPAC Name: 8-hydroxy-5,6,7-trimethoxychromen-2-one
• SMILES (Canonical): COC1=C(C(=C(C2=C1C=CC(=O)O2)O)OC)OC
• SMILES (Isomeric): COC1=C(C(=C(C2=C1C=CC(=O)O2)O)OC)OC
• InChI: InChI=1S/C12H12O6/c1-15-10-6-4-5-7(13)18-9(6)8(14)11(16-2)12(10)17-3/h4-5,14H,1-3H3
• InChI Key: QGXDLWSOPOSJDE-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂O₆
• Molecular Weight: 252.22 g/mol
• Exact Mass: 252.06338810 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• InChI=1/C12H12O6/c1-15-10-6-4-5-7(13)18-9(6)8(14)11(16-2)12(10)17-3/h4-5,14H,1-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9602	96.02%
Caco-2	-	0.5527	55.27%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6514	65.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9165	91.65%
OATP1B3 inhibitior	+	0.9611	96.11%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7331	73.31%
P-glycoprotein inhibitior	-	0.8495	84.95%
P-glycoprotein substrate	-	0.9310	93.10%
CYP3A4 substrate	-	0.6092	60.92%
CYP2C9 substrate	-	0.8431	84.31%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.8520	85.20%
CYP2C9 inhibition	-	0.9867	98.67%
CYP2C19 inhibition	-	0.9199	91.99%
CYP2D6 inhibition	-	0.9293	92.93%
CYP1A2 inhibition	+	0.8260	82.60%
CYP2C8 inhibition	-	0.8173	81.73%
CYP inhibitory promiscuity	-	0.7249	72.49%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5526	55.26%
Eye corrosion	-	0.9701	97.01%
Eye irritation	+	0.8468	84.68%
Skin irritation	-	0.6961	69.61%
Skin corrosion	-	0.9873	98.73%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7342	73.42%
Micronuclear	+	0.8459	84.59%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.9463	94.63%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8390	83.90%
Acute Oral Toxicity (c)	II	0.6827	68.27%
Estrogen receptor binding	+	0.7792	77.92%
Androgen receptor binding	-	0.5555	55.55%
Thyroid receptor binding	-	0.6612	66.12%
Glucocorticoid receptor binding	+	0.5463	54.63%
Aromatase binding	+	0.7287	72.87%
PPAR gamma	+	0.5664	56.64%
Honey bee toxicity	-	0.9355	93.55%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9186	91.86%

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	98.26%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.74%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.27%	94.00%
CHEMBL2581	P07339	Cathepsin D	90.07%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.52%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.65%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.00%	89.00%

Plants that contains it

• Hibiscus syriacus

Cross-Links

• PubChem: 5323870
• NPASS: NPC26673
• LOTUS: LTS0099185
• wikiData: Q105220756