3-(1,1-Dimethylallyl)-7-hydroxy-8-methoxy-chromen-2-one

Details

• Internal ID: bc2cd53e-512a-416a-a740-9cf6ad7211ff
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 7-hydroxy-8-methoxy-3-(2-methylbut-3-en-2-yl)chromen-2-one
• SMILES (Canonical): CC(C)(C=C)C1=CC2=C(C(=C(C=C2)O)OC)OC1=O
• SMILES (Isomeric): CC(C)(C=C)C1=CC2=C(C(=C(C=C2)O)OC)OC1=O
• InChI: InChI=1S/C15H16O4/c1-5-15(2,3)10-8-9-6-7-11(16)13(18-4)12(9)19-14(10)17/h5-8,16H,1H2,2-4H3
• InChI Key: JJIFPBFUGHXSGM-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28 g/mol
• Exact Mass: 260.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.97
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 3-(1,1-dimethylallyl)-7-hydroxy-8-methoxy-chromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9739	97.39%
Caco-2	+	0.7231	72.31%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6555	65.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9287	92.87%
OATP1B3 inhibitior	+	0.9670	96.70%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8477	84.77%
P-glycoprotein inhibitior	-	0.7791	77.91%
P-glycoprotein substrate	-	0.9503	95.03%
CYP3A4 substrate	-	0.5467	54.67%
CYP2C9 substrate	-	0.6506	65.06%
CYP2D6 substrate	-	0.8395	83.95%
CYP3A4 inhibition	+	0.7431	74.31%
CYP2C9 inhibition	-	0.9035	90.35%
CYP2C19 inhibition	-	0.5571	55.71%
CYP2D6 inhibition	-	0.8572	85.72%
CYP1A2 inhibition	-	0.5273	52.73%
CYP2C8 inhibition	-	0.7023	70.23%
CYP inhibitory promiscuity	-	0.6824	68.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4531	45.31%
Eye corrosion	-	0.9825	98.25%
Eye irritation	+	0.7756	77.56%
Skin irritation	-	0.7491	74.91%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5954	59.54%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8222	82.22%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6241	62.41%
Acute Oral Toxicity (c)	III	0.4496	44.96%
Estrogen receptor binding	+	0.8731	87.31%
Androgen receptor binding	+	0.6573	65.73%
Thyroid receptor binding	+	0.7393	73.93%
Glucocorticoid receptor binding	+	0.7219	72.19%
Aromatase binding	+	0.8165	81.65%
PPAR gamma	+	0.7362	73.62%
Honey bee toxicity	-	0.9069	90.69%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9895	98.95%

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	98.52%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.45%	83.82%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	94.35%	80.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.77%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.99%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.74%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.26%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.37%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	85.66%	85.30%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	83.69%	98.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.43%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.88%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.62%	99.17%

Plants that contains it

• Boenninghausenia albiflora
• Pilocarpus riedelianus

Cross-Links

• PubChem: 71588364
• LOTUS: LTS0098161
• wikiData: Q105129670