7-Hydroxy-6,8-bis(3-methylbut-2-enyl)chromen-2-one

Details

• Internal ID: dd54bcf2-56d6-4730-953c-727fff20511c
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 7-hydroxy-6,8-bis(3-methylbut-2-enyl)chromen-2-one
• SMILES (Canonical): CC(=CCC1=C(C(=C2C(=C1)C=CC(=O)O2)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C2C(=C1)C=CC(=O)O2)CC=C(C)C)O)C
• InChI: InChI=1S/C19H22O3/c1-12(2)5-7-14-11-15-8-10-17(20)22-19(15)16(18(14)21)9-6-13(3)4/h5-6,8,10-11,21H,7,9H2,1-4H3
• InChI Key: GSHLMLPFDNHBHO-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.40 g/mol
• Exact Mass: 298.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.52
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 6,8-Diprenyl-7-hydroxy-2H-1-benzopyran-2-one
• 7-hydroxy-6,8-bis(3-methylbut-2-enyl)chromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.6976	69.76%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7920	79.20%
OATP2B1 inhibitior	-	0.5766	57.66%
OATP1B1 inhibitior	+	0.8286	82.86%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6338	63.38%
P-glycoprotein inhibitior	-	0.5275	52.75%
P-glycoprotein substrate	-	0.9150	91.50%
CYP3A4 substrate	-	0.6087	60.87%
CYP2C9 substrate	-	0.5872	58.72%
CYP2D6 substrate	-	0.8258	82.58%
CYP3A4 inhibition	-	0.9312	93.12%
CYP2C9 inhibition	+	0.6066	60.66%
CYP2C19 inhibition	+	0.7739	77.39%
CYP2D6 inhibition	-	0.8667	86.67%
CYP1A2 inhibition	+	0.6481	64.81%
CYP2C8 inhibition	-	0.8072	80.72%
CYP inhibitory promiscuity	+	0.6147	61.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.7174	71.74%
Eye corrosion	-	0.9896	98.96%
Eye irritation	+	0.7390	73.90%
Skin irritation	-	0.6804	68.04%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6161	61.61%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.6677	66.77%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7292	72.92%
Acute Oral Toxicity (c)	III	0.6451	64.51%
Estrogen receptor binding	+	0.9288	92.88%
Androgen receptor binding	+	0.7751	77.51%
Thyroid receptor binding	+	0.5864	58.64%
Glucocorticoid receptor binding	+	0.9067	90.67%
Aromatase binding	+	0.7934	79.34%
PPAR gamma	+	0.9441	94.41%
Honey bee toxicity	-	0.9393	93.93%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.73%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.53%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	93.55%	91.49%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.57%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.52%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.07%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.14%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.40%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.29%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.45%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.86%	99.23%

Plants that contains it

• Asterolasia squamuligera
• Catharanthus roseus
• Cinnamomum chekiangense
• Moringa oleifera
• Pluchea dioscoridis
• Pyrola rotundifolia
• Stevia alpina

Cross-Links

• PubChem: 14769401
• NPASS: NPC294887