5,7-Dihydroxy-2-methyl-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one

Details

• Internal ID: a04376f5-255a-478e-9e33-7256e195384a
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones
• IUPAC Name: 5,7-dihydroxy-2-methyl-8-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C=C(C(=C2O1)CC=C(C)C)O)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C=C(C(=C2O1)CC=C(C)C)O)O
• InChI: InChI=1S/C15H16O4/c1-8(2)4-5-10-11(16)7-13(18)14-12(17)6-9(3)19-15(10)14/h4,6-7,16,18H,5H2,1-3H3
• InChI Key: WUPLGASUDBCHAH-UHFFFAOYSA-N
• Popularity: 1 reference 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): 66.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 5,7-Dihydroxy-2-methyl-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• 5,7-dihydroxy-2-methyl-8-(3-methylbut-2-enyl)chromen-4-one
• SCHEMBL13532119

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.7078	70.78%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6586	65.86%
OATP2B1 inhibitior	-	0.7041	70.41%
OATP1B1 inhibitior	+	0.9280	92.80%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8207	82.07%
P-glycoprotein inhibitior	-	0.7797	77.97%
P-glycoprotein substrate	-	0.8820	88.20%
CYP3A4 substrate	-	0.5483	54.83%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	-	0.6161	61.61%
CYP2C9 inhibition	+	0.8846	88.46%
CYP2C19 inhibition	+	0.8949	89.49%
CYP2D6 inhibition	-	0.6473	64.73%
CYP1A2 inhibition	+	0.9450	94.50%
CYP2C8 inhibition	-	0.8954	89.54%
CYP inhibitory promiscuity	+	0.9133	91.33%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6916	69.16%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.8928	89.28%
Skin irritation	-	0.6962	69.62%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	+	0.5636	56.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.5675	56.75%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.6612	66.12%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6560	65.60%
Acute Oral Toxicity (c)	III	0.6731	67.31%
Estrogen receptor binding	+	0.8165	81.65%
Androgen receptor binding	+	0.6655	66.55%
Thyroid receptor binding	+	0.5564	55.64%
Glucocorticoid receptor binding	+	0.8800	88.00%
Aromatase binding	+	0.6874	68.74%
PPAR gamma	+	0.8805	88.05%
Honey bee toxicity	-	0.8919	89.19%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9931	99.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	97.68%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.39%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.12%	91.49%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.32%	89.34%
CHEMBL2581	P07339	Cathepsin D	92.77%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.72%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.91%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.17%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.05%	96.95%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.59%	91.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.99%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.64%	94.00%

Plants that contains it

• Cedrelopsis grevei

Cross-Links

• PubChem: 12310443
• LOTUS: LTS0108363
• wikiData: Q105313215