(4S)-4-hydroperoxy-3,4,5-trimethylbenzo[f][1]benzofuran-9-one

Details

• Internal ID: 139bf097-1b33-46bd-97b1-2bb718fb44d3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4S)-4-hydroperoxy-3,4,5-trimethylbenzo[f][1]benzofuran-9-one
• SMILES (Canonical): CC1=C2C(=CC=C1)C(=O)C3=C(C2(C)OO)C(=CO3)C
• SMILES (Isomeric): CC1=C2C(=CC=C1)C(=O)C3=C([C@@]2(C)OO)C(=CO3)C
• InChI: InChI=1S/C15H14O4/c1-8-5-4-6-10-11(8)15(3,19-17)12-9(2)7-18-14(12)13(10)16/h4-7,17H,1-3H3/t15-/m0/s1
• InChI Key: WJJDWAGMRXHMKI-HNNXBMFYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.08920892 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9849	98.49%
Caco-2	+	0.7077	70.77%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6044	60.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9056	90.56%
OATP1B3 inhibitior	+	0.9318	93.18%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8394	83.94%
P-glycoprotein inhibitior	-	0.8542	85.42%
P-glycoprotein substrate	-	0.9367	93.67%
CYP3A4 substrate	+	0.5960	59.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7885	78.85%
CYP3A4 inhibition	-	0.7465	74.65%
CYP2C9 inhibition	-	0.7754	77.54%
CYP2C19 inhibition	-	0.6302	63.02%
CYP2D6 inhibition	-	0.8891	88.91%
CYP1A2 inhibition	+	0.6166	61.66%
CYP2C8 inhibition	+	0.4718	47.18%
CYP inhibitory promiscuity	+	0.5414	54.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.4369	43.69%
Eye corrosion	-	0.9564	95.64%
Eye irritation	+	0.6745	67.45%
Skin irritation	-	0.8070	80.70%
Skin corrosion	-	0.9601	96.01%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7489	74.89%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.6888	68.88%
skin sensitisation	-	0.8159	81.59%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.8190	81.90%
Acute Oral Toxicity (c)	III	0.5612	56.12%
Estrogen receptor binding	+	0.6731	67.31%
Androgen receptor binding	+	0.5288	52.88%
Thyroid receptor binding	-	0.5192	51.92%
Glucocorticoid receptor binding	-	0.4796	47.96%
Aromatase binding	+	0.6034	60.34%
PPAR gamma	+	0.5521	55.21%
Honey bee toxicity	-	0.9274	92.74%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9387	93.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.87%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.22%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.28%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.21%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	91.51%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.08%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.76%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.60%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.82%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.35%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.19%	93.65%
CHEMBL1907	P15144	Aminopeptidase N	80.07%	93.31%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.02%	93.10%

Plants that contains it

• Parasenecio hastatus
• Senecio coronatus

Cross-Links

• PubChem: 162952223
• LOTUS: LTS0193272
• wikiData: Q105306819