7,8-Dihydroxy-5-(4-hydroxy-3-methylbut-2-enyl)-6-methoxychromen-2-one

Details

• Internal ID: e22c95db-7490-4a1b-8c19-e2cbb5a3d504
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7,8-dihydroxycoumarins
• IUPAC Name: 7,8-dihydroxy-5-(4-hydroxy-3-methylbut-2-enyl)-6-methoxychromen-2-one
• SMILES (Canonical): CC(=CCC1=C2C=CC(=O)OC2=C(C(=C1OC)O)O)CO
• SMILES (Isomeric): CC(=CCC1=C2C=CC(=O)OC2=C(C(=C1OC)O)O)CO
• InChI: InChI=1S/C15H16O6/c1-8(7-16)3-4-9-10-5-6-11(17)21-15(10)13(19)12(18)14(9)20-2/h3,5-6,16,18-19H,4,7H2,1-2H3
• InChI Key: TVDZWFVHDNZOKZ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₆
• Molecular Weight: 292.28 g/mol
• Exact Mass: 292.09468823 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.69
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8871	88.71%
Caco-2	+	0.5188	51.88%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6934	69.34%
OATP2B1 inhibitior	-	0.5774	57.74%
OATP1B1 inhibitior	+	0.8459	84.59%
OATP1B3 inhibitior	+	0.9442	94.42%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6152	61.52%
P-glycoprotein inhibitior	-	0.8764	87.64%
P-glycoprotein substrate	-	0.7793	77.93%
CYP3A4 substrate	-	0.5146	51.46%
CYP2C9 substrate	-	0.6104	61.04%
CYP2D6 substrate	-	0.8160	81.60%
CYP3A4 inhibition	-	0.7126	71.26%
CYP2C9 inhibition	-	0.6812	68.12%
CYP2C19 inhibition	+	0.5832	58.32%
CYP2D6 inhibition	-	0.7196	71.96%
CYP1A2 inhibition	+	0.7497	74.97%
CYP2C8 inhibition	-	0.6363	63.63%
CYP inhibitory promiscuity	+	0.5792	57.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7259	72.59%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.7509	75.09%
Skin irritation	-	0.7698	76.98%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6339	63.39%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8192	81.92%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9095	90.95%
Acute Oral Toxicity (c)	III	0.5572	55.72%
Estrogen receptor binding	+	0.7676	76.76%
Androgen receptor binding	+	0.5624	56.24%
Thyroid receptor binding	-	0.6510	65.10%
Glucocorticoid receptor binding	+	0.8897	88.97%
Aromatase binding	+	0.5756	57.56%
PPAR gamma	+	0.7732	77.32%
Honey bee toxicity	-	0.8901	89.01%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9954	99.54%

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	99.09%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.79%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.57%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.69%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	89.93%	91.49%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	87.23%	97.88%
CHEMBL3401	O75469	Pregnane X receptor	87.01%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.77%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.52%	99.23%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.07%	89.34%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.19%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.75%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.11%	96.00%

Plants that contains it

• Haplophyllum obtusifolium

Cross-Links

• PubChem: 162851750
• LOTUS: LTS0275105
• wikiData: Q105265228