6,8-Dimethoxycoumarin

Details

• Internal ID: b51b2f11-83bf-4aa2-8285-1569ac636999
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 6,8-dimethoxychromen-2-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)C=CC(=O)O2)OC
• SMILES (Isomeric): COC1=CC(=C2C(=C1)C=CC(=O)O2)OC
• InChI: InChI=1S/C11H10O4/c1-13-8-5-7-3-4-10(12)15-11(7)9(6-8)14-2/h3-6H,1-2H3
• InChI Key: UQUJRRZSWGUHRN-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.19 g/mol
• Exact Mass: 206.05790880 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.81
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 6,8-Dimethoxycumarin
• 6,8-dimethoxychromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9815	98.15%
Caco-2	+	0.5285	52.85%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5320	53.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9564	95.64%
OATP1B3 inhibitior	+	0.9218	92.18%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6119	61.19%
P-glycoprotein inhibitior	-	0.8917	89.17%
P-glycoprotein substrate	-	0.9697	96.97%
CYP3A4 substrate	-	0.6806	68.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8151	81.51%
CYP3A4 inhibition	+	0.5292	52.92%
CYP2C9 inhibition	-	0.8525	85.25%
CYP2C19 inhibition	+	0.5358	53.58%
CYP2D6 inhibition	-	0.8152	81.52%
CYP1A2 inhibition	+	0.9531	95.31%
CYP2C8 inhibition	-	0.8190	81.90%
CYP inhibitory promiscuity	+	0.5466	54.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5381	53.81%
Eye corrosion	-	0.8268	82.68%
Eye irritation	+	0.8748	87.48%
Skin irritation	-	0.6573	65.73%
Skin corrosion	-	0.9879	98.79%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5052	50.52%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.5210	52.10%
skin sensitisation	-	0.9136	91.36%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.4913	49.13%
Acute Oral Toxicity (c)	II	0.5189	51.89%
Estrogen receptor binding	+	0.6834	68.34%
Androgen receptor binding	+	0.6436	64.36%
Thyroid receptor binding	-	0.6662	66.62%
Glucocorticoid receptor binding	-	0.6607	66.07%
Aromatase binding	+	0.6004	60.04%
PPAR gamma	-	0.6583	65.83%
Honey bee toxicity	-	0.9333	93.33%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8596	85.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.88%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.94%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.14%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.11%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.34%	93.99%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.91%	99.15%
CHEMBL4208	P20618	Proteasome component C5	85.06%	90.00%
CHEMBL2581	P07339	Cathepsin D	84.35%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.01%	86.33%
CHEMBL1907	P15144	Aminopeptidase N	80.39%	93.31%
CHEMBL3401	O75469	Pregnane X receptor	80.20%	94.73%

Plants that contains it

• Citrus trifoliata

Cross-Links

• PubChem: 21790450
• LOTUS: LTS0017190
• wikiData: Q105277462