(Aminobenzamidino)succinyl analogue

ID: ALA1160511

PubChem CID: 10472801

Max Phase: Preclinical

Molecular Formula: C17H22N4O4

Molecular Weight: 346.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C[C@H](CC(=O)O)NC(=O)CCC(=O)N(C)c1ccc(C(=N)N)cc1

Standard InChI:  InChI=1S/C17H22N4O4/c1-3-12(10-16(24)25)20-14(22)8-9-15(23)21(2)13-6-4-11(5-7-13)17(18)19/h3-7,12H,1,8-10H2,2H3,(H3,18,19)(H,20,22)(H,24,25)/t12-/m1/s1

Standard InChI Key:  HVGVVJWPNBZAHP-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   -0.8333   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -3.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750   -2.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167    1.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -1.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958   -2.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625    0.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  2  0
  4  8  1  0
 11  5  1  1
  6  5  1  0
  7 23  1  0
  8 18  1  0
  9  1  1  0
 10  7  1  0
 11 10  1  0
 12  2  2  0
 13  2  1  0
 14  6  2  0
 15  7  2  0
 16 11  1  0
 17 19  1  0
 18 20  2  0
 19  9  2  0
 20  9  1  0
 21  1  1  0
 22 16  2  0
 23 13  1  0
 24  6  1  0
 25  4  1  0
 17  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160511

   (3S)-3-[[4-(4-carbamimidoyl-N-methylanilino)-4-oxobutanoyl]amino]pent-4-enoic acid

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: 346.39

Molecular Weight (Monoisotopic): 346.1641

AlogP: 0.86

#Rotatable Bonds: 9

Polar Surface Area: 136.58

Molecular Species: ZWITTERION

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.04

CX Basic pKa: 11.49

CX LogP: -1.90

CX LogD: -1.90

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.30

Np Likeness Score: -0.39

References

1. Zablocki JA, Rico JG, Garland RB, Rogers TE, Williams K, Schretzman LA, Rao SA, Bovy PR, Tjoeng FS, Lindmark RJ..  (1995)  Potent in vitro and in vivo inhibitors of platelet aggregation based upon the Arg-Gly-Asp sequence of fibrinogen. (Aminobenzamidino)succinyl (ABAS) series of orally active fibrinogen receptor antagonists.,  38  (13): [PMID:7608903] [10.1021/jm00013a014]

Source

Source(1):

• Scientific Literature