6-(3-Carboxybut-2-enyl)-7-hydroxycoumarin

Details

• Internal ID: 07f7cc27-be2a-4b70-88da-1021f4433033
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 4-(7-hydroxy-2-oxochromen-6-yl)-2-methylbut-2-enoic acid
• SMILES (Canonical): CC(=CCC1=C(C=C2C(=C1)C=CC(=O)O2)O)C(=O)O
• SMILES (Isomeric): CC(=CCC1=C(C=C2C(=C1)C=CC(=O)O2)O)C(=O)O
• InChI: InChI=1S/C14H12O5/c1-8(14(17)18)2-3-9-6-10-4-5-13(16)19-12(10)7-11(9)15/h2,4-7,15H,3H2,1H3,(H,17,18)
• InChI Key: XUJMUOILFKRGOM-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.24 g/mol
• Exact Mass: 260.06847348 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 6-(3-carboxybut-2-enyl)-7-hydroxycoumarin

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9700	97.00%
Caco-2	+	0.6066	60.66%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7791	77.91%
OATP2B1 inhibitior	-	0.5779	57.79%
OATP1B1 inhibitior	+	0.8924	89.24%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6004	60.04%
P-glycoprotein inhibitior	-	0.9657	96.57%
P-glycoprotein substrate	-	0.8683	86.83%
CYP3A4 substrate	-	0.6280	62.80%
CYP2C9 substrate	+	0.6176	61.76%
CYP2D6 substrate	-	0.8933	89.33%
CYP3A4 inhibition	-	0.8742	87.42%
CYP2C9 inhibition	+	0.9071	90.71%
CYP2C19 inhibition	+	0.5398	53.98%
CYP2D6 inhibition	-	0.8514	85.14%
CYP1A2 inhibition	+	0.5543	55.43%
CYP2C8 inhibition	-	0.7986	79.86%
CYP inhibitory promiscuity	+	0.6061	60.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9713	97.13%
Carcinogenicity (trinary)	Non-required	0.5927	59.27%
Eye corrosion	-	0.9917	99.17%
Eye irritation	+	0.5986	59.86%
Skin irritation	-	0.6188	61.88%
Skin corrosion	-	0.9293	92.93%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7693	76.93%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.7747	77.47%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7582	75.82%
Acute Oral Toxicity (c)	II	0.4446	44.46%
Estrogen receptor binding	+	0.7452	74.52%
Androgen receptor binding	+	0.5963	59.63%
Thyroid receptor binding	-	0.6384	63.84%
Glucocorticoid receptor binding	+	0.8281	82.81%
Aromatase binding	+	0.6232	62.32%
PPAR gamma	+	0.6928	69.28%
Honey bee toxicity	-	0.9686	96.86%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	98.88%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.47%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.27%	94.73%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.44%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.34%	86.33%
CHEMBL3959	P16083	Quinone reductase 2	86.26%	89.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.25%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.90%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.70%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.32%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.65%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.56%	96.00%
CHEMBL4208	P20618	Proteasome component C5	80.65%	90.00%

Plants that contains it

• Peucedanum ostruthium

Cross-Links

• PubChem: 54488943
• LOTUS: LTS0025171
• wikiData: Q105342359