3-{2-[(S)-4-(3-Guanidino-propyl)-2,5-dioxo-imidazolidin-1-yl]-acetylamino}-2-(3-phenyl-propionylamino)-propionic acid anion

ID: ALA1160221

PubChem CID: 44296726

Max Phase: Preclinical

Molecular Formula: C21H29N7O6

Molecular Weight: 475.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@@H]1NC(=O)N(CC(=O)NCC(NC(=O)CCc2ccccc2)C(=O)O)C1=O

Standard InChI:  InChI=1S/C21H29N7O6/c22-20(23)24-10-4-7-14-18(31)28(21(34)27-14)12-17(30)25-11-15(19(32)33)26-16(29)9-8-13-5-2-1-3-6-13/h1-3,5-6,14-15H,4,7-12H2,(H,25,30)(H,26,29)(H,27,34)(H,32,33)(H4,22,23,24)/t14-,15?/m0/s1

Standard InChI Key:  AEAGZWUTWUZZTA-MLCCFXAWSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.7292   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -3.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500   -3.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3125   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1125   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9250   -3.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1250   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7125   -3.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625   -4.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -2.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -1.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9125   -2.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2625   -2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8625   -1.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -3.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8792   -2.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000   -3.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -3.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3250   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1125   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7250   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5500   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5000   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1625   -5.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1125   -4.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9500   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6 17  1  0
  7  6  1  0
  8  1  1  0
  9 22  1  0
 10  6  1  0
 11  8  1  0
 12 10  1  0
 13  2  2  0
 14  9  2  0
 15  3  2  0
 16 11  1  0
 17 16  1  0
 18  7  1  0
 19  7  2  0
 20 11  2  0
 21 12  2  0
 22 28  1  0
 23  9  1  0
 24 12  1  0
 25 24  1  0
 26 25  1  0
  5 27  1  1
 28 31  1  0
 29 26  2  0
 30 26  1  0
 31 27  1  0
 32 29  1  0
 33 30  2  0
 34 33  1  0
  5  4  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160221

   3-[[2-[(4S)-4-[3-(diaminomethylideneamino)propyl]-2,5-dioxoimidazolidin-1-yl]acetyl]amino]-2-(3-phenylpropanoylamino)propanoic 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: 475.51

Molecular Weight (Monoisotopic): 475.2179

AlogP: -1.51

#Rotatable Bonds: 13

Polar Surface Area: 206.81

Molecular Species: ZWITTERION

HBA: 6

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.57

CX Basic pKa: 12.14

CX LogP: -3.33

CX LogD: -3.33

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.08

Np Likeness Score: -0.42

References

1. Peyman A, Wehner V, Knolle J, Stilz HU, Breipohl G, Scheunemann KH, Carniato D, Ruxer JM, Gourvest JF, Gadek TR, Bodary S..  (2000)  RGD mimetics containing a central hydantoin scaffold: alpkha(v)beta3 vs alpha(IIb)beta3 selectivity requirements.,  10  (2): [PMID:10673106] [10.1016/s0960-894x(99)00661-7]

Source

Source(1):

• Scientific Literature