3-[(1-Methyl-1H-indole-2-carbonyl)-amino]-benzoic Acid

ID: ALA4548832

PubChem CID: 155549150

Max Phase: Preclinical

Molecular Formula: C17H14N2O3

Molecular Weight: 294.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(C(=O)Nc2cccc(C(=O)O)c2)cc2ccccc21

Standard InChI:  InChI=1S/C17H14N2O3/c1-19-14-8-3-2-5-11(14)10-15(19)16(20)18-13-7-4-6-12(9-13)17(21)22/h2-10H,1H3,(H,18,20)(H,21,22)

Standard InChI Key:  SOUMOJNAFCQLEE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.6025   -8.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6013   -9.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3161  -10.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -8.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0296   -8.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0299   -9.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8159   -9.8856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3014   -9.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8155   -8.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711  -10.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1245   -9.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5377   -9.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5363   -8.5012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3612   -8.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7726   -9.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5968   -9.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0094   -8.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5918   -7.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7689   -7.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0010   -7.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8260   -7.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5853   -6.3545    0.0000 O   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
  7 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548832

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 294.31

Molecular Weight (Monoisotopic): 294.1004

AlogP: 3.13

#Rotatable Bonds: 3

Polar Surface Area: 71.33

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.92

CX Basic pKa: ┄

CX LogP: 2.97

CX LogD: -0.24

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: -1.25

References

1. Weinstabl H, Treu M, Rinnenthal J, Zahn SK, Ettmayer P, Bader G, Dahmann G, Kessler D, Rumpel K, Mischerikow N, Savarese F, Gerstberger T, Mayer M, Zoephel A, Schnitzer R, Sommergruber W, Martinelli P, Arnhof H, Peric-Simov B, Hofbauer KS, Garavel G, Scherbantin Y, Mitzner S, Fett TN, Scholz G, Bruchhaus J, Burkard M, Kousek R, Ciftci T, Sharps B, Schrenk A, Harrer C, Haering D, Wolkerstorfer B, Zhang X, Lv X, Du A, Li D, Li Y, Quant J, Pearson M, McConnell DB..  (2019)  Intracellular Trapping of the Selective Phosphoglycerate Dehydrogenase (PHGDH) Inhibitor BI-4924 Disrupts Serine Biosynthesis.,  62  (17): [PMID:31365252] [10.1021/acs.jmedchem.9b00718]

Source

Source(1):

• Scientific Literature