[(1S)-2-methyl-4-oxo-3-[(1E,3E)-penta-1,3-dienyl]cyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate

Details

• Internal ID: b951ccf2-4fd6-4a8c-8550-09221769a32e
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Pyrethroids
• IUPAC Name: [(1S)-2-methyl-4-oxo-3-[(1E,3E)-penta-1,3-dienyl]cyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• SMILES (Canonical): CC=CC=CC1=C(C(CC1=O)OC(=O)C2C(C2(C)C)C=C(C)C(=O)OC)C
• SMILES (Isomeric): C/C=C/C=C/C1=C([C@H](CC1=O)OC(=O)[C@@H]2[C@H](C2(C)C)/C=C(\C)/C(=O)OC)C
• InChI: InChI=1S/C22H28O5/c1-7-8-9-10-15-14(3)18(12-17(15)23)27-21(25)19-16(22(19,4)5)11-13(2)20(24)26-6/h7-11,16,18-19H,12H2,1-6H3/b8-7+,10-9+,13-11+/t16-,18+,19+/m1/s1
• InChI Key: FMTMVRQXQWCAJD-MYNFDYRYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.50 g/mol
• Exact Mass: 372.19367399 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.71
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.6252	62.52%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7637	76.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8702	87.02%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9633	96.33%
P-glycoprotein inhibitior	+	0.7133	71.33%
P-glycoprotein substrate	-	0.6224	62.24%
CYP3A4 substrate	+	0.6490	64.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9131	91.31%
CYP3A4 inhibition	-	0.8879	88.79%
CYP2C9 inhibition	-	0.8598	85.98%
CYP2C19 inhibition	-	0.7444	74.44%
CYP2D6 inhibition	-	0.9546	95.46%
CYP1A2 inhibition	-	0.8303	83.03%
CYP2C8 inhibition	-	0.6530	65.30%
CYP inhibitory promiscuity	-	0.8848	88.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6976	69.76%
Carcinogenicity (trinary)	Non-required	0.5812	58.12%
Eye corrosion	-	0.9456	94.56%
Eye irritation	-	0.9417	94.17%
Skin irritation	-	0.6615	66.15%
Skin corrosion	-	0.9679	96.79%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7138	71.38%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	+	0.4830	48.30%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	+	0.9305	93.05%
Acute Oral Toxicity (c)	III	0.4363	43.63%
Estrogen receptor binding	+	0.7500	75.00%
Androgen receptor binding	+	0.5298	52.98%
Thyroid receptor binding	+	0.6584	65.84%
Glucocorticoid receptor binding	+	0.7965	79.65%
Aromatase binding	-	0.5275	52.75%
PPAR gamma	+	0.5455	54.55%
Honey bee toxicity	+	0.8481	84.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9341	93.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.84%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.15%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.94%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	90.80%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.63%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.22%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.74%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.31%	94.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.22%	95.50%

Plants that contains it

• Tanacetum cinerariifolium

Cross-Links

• PubChem: 101037944
• NPASS: NPC165699