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cinerin II

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID b266d83d-40b7-485e-9a4a-11b17d0e7b48
Taxonomy Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Pyrethroids
IUPAC Name [(1S)-3-[(Z)-but-2-enyl]-2-methyl-4-oxocyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
SMILES (Canonical) CC=CCC1=C(C(CC1=O)OC(=O)C2C(C2(C)C)C=C(C)C(=O)OC)C
SMILES (Isomeric) C/C=C\CC1=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/C21H28O5/c1-7-8-9-14-13(3)17(11-16(14)22)26-20(24)18-15(21(18,4)5)10-12(2)19(23)25-6/h7-8,10,15,17-18H,9,11H2,1-6H3/b8-7-,12-10+/t15-,17+,18+/m1/s1
InChI Key SHCRDCOTRILILT-WOBDGSLYSA-N
Popularity 68 references in papers

Physical and Chemical Properties

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Molecular Formula C21H28O5
Molecular Weight 360.40 g/mol
Exact Mass 360.19367399 g/mol
Topological Polar Surface Area (TPSA) 69.70 Ų
XlogP 4.00
Atomic LogP (AlogP) 3.55
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 6

Synonyms

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121-20-0
J204A0Y0JG
[(1S)-3-[(Z)-but-2-enyl]-2-methyl-4-oxocyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
3-(3-Methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester
Cinerine II
(1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate
[3-[(E)-but-2-enyl]-2-methyl-4-oxocyclopent-2-en-1-yl] 3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)cyclopropanecarboxylate
Cyclopropanecarboxylicacid, 3-[(1E)-3-methoxy-2-methyl-3-oxo-1-propen-1-yl]-2,2-dimethyl-,(1S)-3-(2Z)-2-buten-1-yl-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R,3R)-
Cinerin II [BSI:ISO]
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of cinerin II

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9863 98.63%
Caco-2 + 0.6542 65.42%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.8252 82.52%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8728 87.28%
OATP1B3 inhibitior + 0.9139 91.39%
MATE1 inhibitior - 0.6800 68.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.9329 93.29%
P-glycoprotein inhibitior + 0.6325 63.25%
P-glycoprotein substrate - 0.5769 57.69%
CYP3A4 substrate + 0.6108 61.08%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9131 91.31%
CYP3A4 inhibition - 0.8971 89.71%
CYP2C9 inhibition - 0.8298 82.98%
CYP2C19 inhibition - 0.6895 68.95%
CYP2D6 inhibition - 0.9516 95.16%
CYP1A2 inhibition - 0.8643 86.43%
CYP2C8 inhibition - 0.6704 67.04%
CYP inhibitory promiscuity - 0.8719 87.19%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.7176 71.76%
Carcinogenicity (trinary) Non-required 0.6353 63.53%
Eye corrosion - 0.9595 95.95%
Eye irritation - 0.9292 92.92%
Skin irritation - 0.6847 68.47%
Skin corrosion - 0.9825 98.25%
Ames mutagenesis + 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7132 71.32%
Micronuclear - 0.6000 60.00%
Hepatotoxicity + 0.5302 53.02%
skin sensitisation - 0.5795 57.95%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity - 0.5556 55.56%
Mitochondrial toxicity - 0.7250 72.50%
Nephrotoxicity + 0.7093 70.93%
Acute Oral Toxicity (c) II 0.6811 68.11%
Estrogen receptor binding + 0.7409 74.09%
Androgen receptor binding + 0.7178 71.78%
Thyroid receptor binding + 0.6200 62.00%
Glucocorticoid receptor binding + 0.7571 75.71%
Aromatase binding - 0.4836 48.36%
PPAR gamma - 0.5832 58.32%
Honey bee toxicity + 0.8558 85.58%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.7500 75.00%
Fish aquatic toxicity + 0.9854 98.54%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4040 P28482 MAP kinase ERK2 96.64% 83.82%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.31% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.13% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.42% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.61% 85.14%
CHEMBL340 P08684 Cytochrome P450 3A4 90.13% 91.19%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.92% 99.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.80% 95.56%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 84.38% 94.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.28% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.84% 97.09%
CHEMBL3230 O95977 Sphingosine 1-phosphate receptor Edg-6 82.83% 94.01%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.62% 91.07%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 80.27% 96.95%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Tanacetum coccineum

Cross-Links

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PubChem 5281548
LOTUS LTS0027167
wikiData Q27106173