N-Acetyl-I(2)-methyl-L-phenylalanine (1R,2E,4Z,6E)-7-carboxy-1-[(2S)-2-methyl-2-oxiranyl]-2,4,6-heptatrien-1-yl ester

Details

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Internal ID 0538937c-c43c-4d46-8fff-07f97386a369
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > N-acyl-alpha amino acids and derivatives
IUPAC Name 8-(2-acetamido-3-phenylbutanoyl)oxy-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid
SMILES (Canonical) CC(C1=CC=CC=C1)C(C(=O)OC(C=CC=CC=CC(=O)O)C2(CO2)C)NC(=O)C
SMILES (Isomeric) CC(C1=CC=CC=C1)C(C(=O)OC(C=CC=CC=CC(=O)O)C2(CO2)C)NC(=O)C
InChI InChI=1S/C23H27NO6/c1-16(18-11-7-6-8-12-18)21(24-17(2)25)22(28)30-19(23(3)15-29-23)13-9-4-5-10-14-20(26)27/h4-14,16,19,21H,15H2,1-3H3,(H,24,25)(H,26,27)
InChI Key HGSOUJPIFSDBKJ-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C23H27NO6
Molecular Weight 413.50 g/mol
Exact Mass 413.18383758 g/mol
Topological Polar Surface Area (TPSA) 105.00 Ų
XlogP 2.80
Atomic LogP (AlogP) 2.75
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 10

Synonyms

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N-Acetyl-beta-methyl-L-phenylalanine (1R,2E,4Z,6E)-7-carboxy-1-[(2S)-2-methyl-2-oxiranyl]-2,4,6-heptatrien-1-yl ester

2D Structure

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2D Structure of N-Acetyl-I(2)-methyl-L-phenylalanine (1R,2E,4Z,6E)-7-carboxy-1-[(2S)-2-methyl-2-oxiranyl]-2,4,6-heptatrien-1-yl ester

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9026 90.26%
Caco-2 - 0.6315 63.15%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Mitochondria 0.5752 57.52%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9045 90.45%
OATP1B3 inhibitior + 0.9309 93.09%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9005 90.05%
P-glycoprotein inhibitior + 0.6874 68.74%
P-glycoprotein substrate - 0.6383 63.83%
CYP3A4 substrate + 0.6052 60.52%
CYP2C9 substrate - 0.6069 60.69%
CYP2D6 substrate - 0.8992 89.92%
CYP3A4 inhibition - 0.7177 71.77%
CYP2C9 inhibition - 0.6209 62.09%
CYP2C19 inhibition - 0.7346 73.46%
CYP2D6 inhibition - 0.8474 84.74%
CYP1A2 inhibition - 0.7916 79.16%
CYP2C8 inhibition - 0.7812 78.12%
CYP inhibitory promiscuity - 0.7645 76.45%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.7428 74.28%
Carcinogenicity (trinary) Non-required 0.6451 64.51%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9740 97.40%
Skin irritation - 0.7754 77.54%
Skin corrosion - 0.9629 96.29%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8107 81.07%
Micronuclear + 0.6700 67.00%
Hepatotoxicity - 0.5447 54.47%
skin sensitisation - 0.8267 82.67%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity - 0.5222 52.22%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity + 0.6482 64.82%
Acute Oral Toxicity (c) III 0.6156 61.56%
Estrogen receptor binding + 0.7351 73.51%
Androgen receptor binding + 0.5308 53.08%
Thyroid receptor binding + 0.6112 61.12%
Glucocorticoid receptor binding + 0.6096 60.96%
Aromatase binding - 0.5000 50.00%
PPAR gamma - 0.5554 55.54%
Honey bee toxicity - 0.6824 68.24%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.8896 88.96%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.63% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 96.48% 90.17%
CHEMBL4040 P28482 MAP kinase ERK2 95.35% 83.82%
CHEMBL2581 P07339 Cathepsin D 93.93% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.50% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.17% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.70% 86.33%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.43% 95.50%
CHEMBL5028 O14672 ADAM10 88.17% 97.50%
CHEMBL3401 O75469 Pregnane X receptor 88.05% 94.73%
CHEMBL3359 P21462 Formyl peptide receptor 1 87.49% 93.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.12% 96.09%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 85.52% 94.62%
CHEMBL340 P08684 Cytochrome P450 3A4 83.69% 91.19%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.50% 96.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 82.06% 94.08%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.55% 91.07%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.74% 100.00%

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.
Pseudogynoxys sonchoides

Cross-Links

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PubChem 158741
LOTUS LTS0241206
wikiData Q104908521