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  3. (S)-methyl 2-acetamido-4-(2-(methylamino)phenyl)-4-oxobutanoate

SCS-C006187

(S)-methyl 2-acetamido-4-(2-(methylamino)phenyl)-4-oxobutanoate

Pathway: Alkaloids Superclass: Anthranilic acid alkaloids
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Chemical Structure

Structure of (S)-methyl 2-acetamido-4-(2-(methylamino)phenyl)-4-oxobutanoate
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

Source Information

Penicillium sp. (soft coral-derived fungus)
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA
South China Sea
DOI: 10.3390/md17070398  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
278.3 Da
Threshold ≤ 500
ALogP
0.98
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C14H18N2O4
Molecular Weight:
278.3080 Da
SMILES:
CNc1ccccc1C(=O)C[C@H](NC(C)=O)C(=O)OC
InChIKey:
MJJGMIZYROXQLJ-LBPRGKRZSA-N
InChI:
InChI=1S/C14H18N2O4/c1-9(17)16-12(14(19)20-3)8-13(18)10-6-4-5-7-11(10)15-2/h4-7,12,15H,8H2,1-3H3,(H,16,17)/t12-/m0/s1
Calculated Properties
ALogP:
0.979 lipophilicity
TPSA:
84.50 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
6
Ring Count:
1 (1 aromatic)
Chiral Centers:
1
Fsp³:
0.3571 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006187
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Anthranilic acid alkaloids
NPClassifier Class:
N/A
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.
Activity Assay Target / model Result Reference
Antitumor — human gastric cancer cells MGC803, human breast cancer cells MDA-MB-231, human prostate cancer cells C4-2B, human osteosarcoma 143B, human lung cancer cells A549 > 5.0 μM 10.3390/md17070398 Marine Drugs
Antibacterial — A. baumannii, K. pneumoniae, E. coli, S. aureus, E. faecalis > 100.0 μg/mL 10.3390/md17070398 Marine Drugs
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Structure enlarged