[2-(1H-Indol-3-yl)-2-oxo-acetylamino]-acetic acid methyl ester

ID: ALA3113607

PubChem CID: 76328546

Max Phase: Preclinical

Molecular Formula: C13H12N2O4

Molecular Weight: 260.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CNC(=O)C(=O)c1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C13H12N2O4/c1-19-11(16)7-15-13(18)12(17)9-6-14-10-5-3-2-4-8(9)10/h2-6,14H,7H2,1H3,(H,15,18)

Standard InChI Key:  JIEDITNOGMMUSG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    0.3902  -22.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891  -22.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038  -23.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021  -21.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174  -22.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8176  -22.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081  -23.2363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0964  -22.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073  -21.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0140  -21.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8389  -21.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958  -20.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571  -21.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2456  -20.4513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0706  -20.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4773  -19.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3023  -19.7205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0592  -19.0159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7205  -20.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  2  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113607

   methyl 2-[[2-(1H-indol-3-yl)-2-oxoacetyl]amino]acetate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 260.25

Molecular Weight (Monoisotopic): 260.0797

AlogP: 0.64

#Rotatable Bonds: 4

Polar Surface Area: 88.26

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.56

CX Basic pKa: ┄

CX LogP: 0.63

CX LogD: 0.63

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.48

Np Likeness Score: -0.58

References

1. Prasher P, Pooja, Singh P..  (2014)  Lead modification: amino acid appended indoles as highly effective 5-LOX inhibitors.,  22  (5): [PMID:24508141] [10.1016/j.bmc.2014.01.027]

2. Mishra S, Kaur M, Chander S, Murugesan S, Nim L, Arora DS, Singh P..  (2018)  Rational modification of a lead molecule: Improving the antifungal activity of indole - triazole - amino acid conjugates.,  155  [PMID:29936353] [10.1016/j.ejmech.2018.06.039]

Source

Source(1):

• Scientific Literature