7-[(E,3R)-4-hydroxy-3-methylbut-1-enoxy]chromen-2-one

Details

• Internal ID: 81b8d311-bbc9-4222-8080-74a1c874d0b3
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 7-[(E,3R)-4-hydroxy-3-methylbut-1-enoxy]chromen-2-one
• SMILES (Canonical): CC(CO)C=COC1=CC2=C(C=C1)C=CC(=O)O2
• SMILES (Isomeric): C[C@@H](CO)/C=C/OC1=CC2=C(C=C1)C=CC(=O)O2
• InChI: InChI=1S/C14H14O4/c1-10(9-15)6-7-17-12-4-2-11-3-5-14(16)18-13(11)8-12/h2-8,10,15H,9H2,1H3/b7-6+/t10-/m1/s1
• InChI Key: JAYZSRBMHBCFRV-VQCYPWCPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26 g/mol
• Exact Mass: 246.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	+	0.6694	66.94%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5212	52.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7966	79.66%
OATP1B3 inhibitior	+	0.9686	96.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5750	57.50%
P-glycoprotein inhibitior	-	0.9004	90.04%
P-glycoprotein substrate	-	0.9089	90.89%
CYP3A4 substrate	-	0.5779	57.79%
CYP2C9 substrate	-	0.6285	62.85%
CYP2D6 substrate	-	0.8504	85.04%
CYP3A4 inhibition	-	0.6144	61.44%
CYP2C9 inhibition	-	0.6008	60.08%
CYP2C19 inhibition	+	0.5930	59.30%
CYP2D6 inhibition	-	0.8892	88.92%
CYP1A2 inhibition	+	0.6721	67.21%
CYP2C8 inhibition	-	0.8981	89.81%
CYP inhibitory promiscuity	+	0.6071	60.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9113	91.13%
Carcinogenicity (trinary)	Non-required	0.5329	53.29%
Eye corrosion	-	0.9595	95.95%
Eye irritation	-	0.7360	73.60%
Skin irritation	-	0.7210	72.10%
Skin corrosion	-	0.9804	98.04%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6172	61.72%
Micronuclear	+	0.6674	66.74%
Hepatotoxicity	-	0.6496	64.96%
skin sensitisation	-	0.8234	82.34%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7450	74.50%
Acute Oral Toxicity (c)	III	0.6183	61.83%
Estrogen receptor binding	+	0.8380	83.80%
Androgen receptor binding	+	0.6708	67.08%
Thyroid receptor binding	-	0.7290	72.90%
Glucocorticoid receptor binding	+	0.5753	57.53%
Aromatase binding	+	0.9331	93.31%
PPAR gamma	+	0.6085	60.85%
Honey bee toxicity	-	0.9178	91.78%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9631	96.31%

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	96.36%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.20%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.35%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.41%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.84%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.03%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.56%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.88%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.78%	96.00%
CHEMBL4208	P20618	Proteasome component C5	82.90%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.57%	86.92%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.85%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.32%	86.33%

Plants that contains it

• Ammi majus

Cross-Links

• PubChem: 163185356
• LOTUS: LTS0153211
• wikiData: Q105124164