SID49671582

ID: ALA1452863

Cas Number: 10129-16-5

PubChem CID: 1215342

Max Phase: Preclinical

Molecular Formula: C21H16N2O4

Molecular Weight: 360.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-[2-(Benzoylamino)Benzoylamino]Benzoic Acid | Benzavir-1|2-[(2-benzamidobenzoyl)amino]benzoic acid|10129-16-5|2-(2-BENZAMIDOBENZAMIDO)BENZOIC ACID|Maybridge4_000178|Cambridge id 5263624|Oprea1_095240|MLS001181446|CHEMBL1452863|SCHEMBL14855554|QNNOKAUNPFYKNS-UHFFFAOYSA-N|HMS1521I04|HMS2859H18|AKOS003302080|IDI1_030760|SMR000567150|2-[2-(Benzoylamino)Benzoylamino]Benzoic Acid|2-[[2-(Benzoylamino)benzoyl]amino]benzoic acid|EN300-33364232|Z57175081

Canonical SMILES:  O=C(Nc1ccccc1C(=O)Nc1ccccc1C(=O)O)c1ccccc1

Standard InChI:  InChI=1S/C21H16N2O4/c24-19(14-8-2-1-3-9-14)22-17-12-6-4-10-15(17)20(25)23-18-13-7-5-11-16(18)21(26)27/h1-13H,(H,22,24)(H,23,25)(H,26,27)

Standard InChI Key:  QNNOKAUNPFYKNS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -0.8763   -1.1407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671   -2.3782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4487    0.0968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7342   -1.1407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053   -1.1407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619   -2.3782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763   -2.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908   -1.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053   -0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198    0.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053   -2.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -2.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763   -3.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    0.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7342   -0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198    0.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053   -3.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    0.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053    1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671   -4.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619   -4.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -5.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0
  2 13  2  0
  3 16  2  0
  4 16  1  0
  5  9  1  0
  5 10  1  0
  6  8  1  0
  6 13  1  0
  7  8  1  0
  7  9  1  0
  7 12  2  0
  8 14  2  0
 10 11  1  0
 10 15  2  0
 11 16  1  0
 11 18  2  0
 12 19  1  0
 13 17  1  0
 14 20  1  0
 15 21  1  0
 17 23  2  0
 17 24  1  0
 18 22  1  0
 19 20  2  0
 21 22  2  0
 23 25  1  0
 24 26  2  0
 25 27  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1452863

   2-[(2-Benzamidobenzoyl)amino]benzoic acid

Molecule Features

Natural Product: Yes

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: 360.37

Molecular Weight (Monoisotopic): 360.1110

AlogP: 3.89

#Rotatable Bonds: 5

Polar Surface Area: 95.50

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: ┄

CX LogP: 4.46

CX LogD: 1.11

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.81

References

1. PubChem BioAssay data set, 

2. Andersson EK, Strand M, Edlund K, Lindman K, Enquist PA, Spjut S, Allard A, Elofsson M, Mei YF, Wadell G..  (2010)  Small-molecule screening using a whole-cell viral replication reporter gene assay identifies 2-{[2-(benzoylamino)benzoyl]amino}-benzoic acid as a novel antiadenoviral compound.,  54  (9): [PMID:20585112] [10.1128/aac.00203-10]

3. Öberg CT, Strand M, Andersson EK, Edlund K, Tran NP, Mei YF, Wadell G, Elofsson M..  (2012)  Synthesis, biological evaluation, and structure-activity relationships of 2-[2-(benzoylamino)benzoylamino]benzoic acid analogues as inhibitors of adenovirus replication.,  55  (7): [PMID:22369233] [10.1021/jm201636v]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays