3-[5-(4-Carbamimidoyl-phenyl)-pent-4-enoylamino]-pent-4-enoic acid

ID: ALA1160510

PubChem CID: 10335848

Max Phase: Preclinical

Molecular Formula: C17H21N3O3

Molecular Weight: 315.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H21N3O3/c1-2-14(11-16(22)23)20-15(21)6-4-3-5-12-7-9-13(10-8-12)17(18)19/h2-3,5,7-10,14H,1,4,6,11H2,(H3,18,19)(H,20,21)(H,22,23)/b5-3+/t14-/m1/s1

Standard InChI Key:  XYGJYKGSUZQMGE-LYKUJDHUSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  1  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
   -0.7250   -3.7917    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
   -0.3625   -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
    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
    1.0250   -1.6875    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
    1.5792   -1.9000    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
    0.5625   -2.0625    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
    0.0042   -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
    2.6000   -1.7292    0.0000 C   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
  2  1  2  0
  8  3  1  1
  4  3  1  0
  5 22  1  0
  6  1  1  0
  7  5  1  0
  8  7  1  0
  9  4  2  0
 10  5  2  0
 11  8  1  0
 12 18  1  0
 13  6  2  0
 14  6  1  0
 15 12  2  0
 16  1  1  0
 17 11  2  0
 18 21  1  0
 19  4  1  0
 20 13  1  0
 21 14  2  0
 22 23  1  0
 23 15  1  0
 20 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160510

   (3S)-3-[[(E)-5-(4-carbamimidoylphenyl)pent-4-enoyl]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: 315.37

Molecular Weight (Monoisotopic): 315.1583

AlogP: 1.91

#Rotatable Bonds: 9

Polar Surface Area: 116.27

Molecular Species: ZWITTERION

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.21

CX Basic pKa: 11.57

CX LogP: -0.14

CX LogD: -0.14

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.32

Np Likeness Score: 0.79

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