8-[(2S)-2-Hydroperoxy-3-methyl-3-buten-1-yl]-7-methoxy-2H-1-benzopyran-2-one

Details

• Internal ID: 7ed667f5-a18d-4db2-806f-3f98d9631974
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 8-[(2S)-2-hydroperoxy-3-methylbut-3-enyl]-7-methoxychromen-2-one
• SMILES (Canonical): CC(=C)C(CC1=C(C=CC2=C1OC(=O)C=C2)OC)OO
• SMILES (Isomeric): CC(=C)[C@H](CC1=C(C=CC2=C1OC(=O)C=C2)OC)OO
• InChI: InChI=1S/C15H16O5/c1-9(2)13(20-17)8-11-12(18-3)6-4-10-5-7-14(16)19-15(10)11/h4-7,13,17H,1,8H2,2-3H3/t13-/m0/s1
• InChI Key: FQGUIRNHNGZCNL-ZDUSSCGKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• DTXSID201141328
• 8-[(2S)-2-Hydroperoxy-3-methyl-3-buten-1-yl]-7-methoxy-2H-1-benzopyran-2-one
• 109741-39-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	-	0.5886	58.86%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6208	62.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9116	91.16%
OATP1B3 inhibitior	+	0.9197	91.97%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5792	57.92%
P-glycoprotein inhibitior	-	0.7958	79.58%
P-glycoprotein substrate	-	0.7552	75.52%
CYP3A4 substrate	-	0.5375	53.75%
CYP2C9 substrate	-	0.6506	65.06%
CYP2D6 substrate	-	0.8126	81.26%
CYP3A4 inhibition	-	0.5625	56.25%
CYP2C9 inhibition	-	0.6259	62.59%
CYP2C19 inhibition	+	0.5433	54.33%
CYP2D6 inhibition	-	0.8638	86.38%
CYP1A2 inhibition	+	0.5411	54.11%
CYP2C8 inhibition	-	0.7339	73.39%
CYP inhibitory promiscuity	+	0.6542	65.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8713	87.13%
Carcinogenicity (trinary)	Non-required	0.6865	68.65%
Eye corrosion	-	0.9781	97.81%
Eye irritation	-	0.8802	88.02%
Skin irritation	-	0.7595	75.95%
Skin corrosion	-	0.9445	94.45%
Ames mutagenesis	+	0.5163	51.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5445	54.45%
Micronuclear	+	0.5559	55.59%
Hepatotoxicity	+	0.6306	63.06%
skin sensitisation	-	0.7714	77.14%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.5876	58.76%
Acute Oral Toxicity (c)	III	0.4773	47.73%
Estrogen receptor binding	-	0.4913	49.13%
Androgen receptor binding	+	0.5490	54.90%
Thyroid receptor binding	-	0.5624	56.24%
Glucocorticoid receptor binding	-	0.5428	54.28%
Aromatase binding	+	0.5718	57.18%
PPAR gamma	+	0.7210	72.10%
Honey bee toxicity	-	0.7587	75.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9929	99.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.54%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	93.18%	90.20%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.46%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	91.60%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	91.04%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.19%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.35%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.78%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.16%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.61%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.62%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.55%	96.00%

Plants that contains it

• Murraya paniculata

Cross-Links

• PubChem: 13917395
• LOTUS: LTS0182110
• wikiData: Q104999643