6-hydroxy-7-[(E)-4-hydroxy-3-methylbut-2-enoxy]chromen-2-one

Details

• Internal ID: 93b357bc-df23-48c1-b786-ccaa5a37ca2f
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins
• IUPAC Name: 6-hydroxy-7-[(E)-4-hydroxy-3-methylbut-2-enoxy]chromen-2-one
• SMILES (Canonical): CC(=CCOC1=C(C=C2C=CC(=O)OC2=C1)O)CO
• SMILES (Isomeric): C/C(=C\COC1=C(C=C2C=CC(=O)OC2=C1)O)/CO
• InChI: InChI=1S/C14H14O5/c1-9(8-15)4-5-18-13-7-12-10(6-11(13)16)2-3-14(17)19-12/h2-4,6-7,15-16H,5,8H2,1H3/b9-4+
• InChI Key: KIKJJTKUYYKDFT-RUDMXATFSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.26 g/mol
• Exact Mass: 262.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9389	93.89%
Caco-2	+	0.7061	70.61%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6981	69.81%
OATP2B1 inhibitior	-	0.7210	72.10%
OATP1B1 inhibitior	+	0.9205	92.05%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5615	56.15%
P-glycoprotein inhibitior	-	0.8873	88.73%
P-glycoprotein substrate	-	0.8151	81.51%
CYP3A4 substrate	-	0.5502	55.02%
CYP2C9 substrate	-	0.6435	64.35%
CYP2D6 substrate	-	0.8323	83.23%
CYP3A4 inhibition	-	0.8473	84.73%
CYP2C9 inhibition	-	0.5538	55.38%
CYP2C19 inhibition	+	0.6712	67.12%
CYP2D6 inhibition	-	0.7265	72.65%
CYP1A2 inhibition	+	0.6919	69.19%
CYP2C8 inhibition	-	0.6799	67.99%
CYP inhibitory promiscuity	+	0.8019	80.19%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6612	66.12%
Eye corrosion	-	0.9883	98.83%
Eye irritation	+	0.5554	55.54%
Skin irritation	-	0.7539	75.39%
Skin corrosion	-	0.9568	95.68%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6649	66.49%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8157	81.57%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4601	46.01%
Acute Oral Toxicity (c)	III	0.5588	55.88%
Estrogen receptor binding	+	0.8823	88.23%
Androgen receptor binding	+	0.5837	58.37%
Thyroid receptor binding	-	0.6085	60.85%
Glucocorticoid receptor binding	+	0.7882	78.82%
Aromatase binding	+	0.8809	88.09%
PPAR gamma	+	0.8329	83.29%
Honey bee toxicity	-	0.9269	92.69%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9959	99.59%

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	97.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.74%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.12%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.09%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.08%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	89.07%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.67%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.29%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	85.35%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.27%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.98%	99.15%
CHEMBL4208	P20618	Proteasome component C5	80.52%	90.00%

Plants that contains it

• Haplopappus multifolius

Cross-Links

• PubChem: 102187242
• LOTUS: LTS0155530
• wikiData: Q105141563