2-Benzyloxycarbonylamino-3-{2-[(S)-4-(2-guanidino-ethyl)-2,5-dioxo-imidazolidin-1-yl]-acetylamino}-propionic acid anion

ID: ALA1160222

PubChem CID: 44296742

Max Phase: Preclinical

Molecular Formula: C19H25N7O7

Molecular Weight: 463.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCC[C@@H]1NC(=O)N(CC(=O)NCC(NC(=O)OCc2ccccc2)C(=O)O)C1=O

Standard InChI:  InChI=1S/C19H25N7O7/c20-17(21)22-7-6-12-15(28)26(18(31)24-12)9-14(27)23-8-13(16(29)30)25-19(32)33-10-11-4-2-1-3-5-11/h1-5,12-13H,6-10H2,(H,23,27)(H,24,31)(H,25,32)(H,29,30)(H4,20,21,22)/t12-,13?/m0/s1

Standard InChI Key:  MIKCNEPEXKKSOM-UEWDXFNNSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    4.0417   -0.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -1.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6250   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0250   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2375   -1.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -2.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750    0.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8375   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5750   -0.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1917   -0.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1750    0.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6375   -1.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -1.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4250   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0375   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8625   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8125   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4250   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4750   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2625   -3.3542    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  9  1  0
  8  6  1  0
  9  6  1  0
 10  1  1  0
 11 23  1  0
 12 10  1  0
 13  2  2  0
 14 11  2  0
 15  3  2  0
 16 12  1  0
 17 16  1  0
 18  8  1  0
 19  7  2  0
 20  8  2  0
 21  7  1  0
 22 12  2  0
 23 27  1  0
 24 11  1  0
  5 25  1  1
 26 21  1  0
 27 25  1  0
 28 26  1  0
 29 28  2  0
 30 28  1  0
 31 30  2  0
 32 29  1  0
 33 31  1  0
  5  4  1  0
 32 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160222

   3-[[2-[(4S)-4-[2-(diaminomethylideneamino)ethyl]-2,5-dioxoimidazolidin-1-yl]acetyl]amino]-2-(phenylmethoxycarbonylamino)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: 463.45

Molecular Weight (Monoisotopic): 463.1815

AlogP: -1.72

#Rotatable Bonds: 11

Polar Surface Area: 216.04

Molecular Species: ZWITTERION

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.42

CX Basic pKa: 12.17

CX LogP: -3.78

CX LogD: -3.78

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.11

Np Likeness Score: -0.58

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