2-Benzyloxycarbonylamino-3-(2-{(S)-4-[N'-(4,5-dihydro-1H-imidazol-2-yl)-hydrazinocarbonylmethyl]-2,5-dioxo-imidazolidin-1-yl}-acetylamino)-propionic acid anion

ID: ALA1160226

PubChem CID: 44296864

Max Phase: Preclinical

Molecular Formula: C21H26N8O8

Molecular Weight: 518.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)N[C@@H](CC(=O)NNC2=NCCN2)C1=O)NCC(NC(=O)OCc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C21H26N8O8/c30-15(27-28-19-22-6-7-23-19)8-13-17(32)29(20(35)25-13)10-16(31)24-9-14(18(33)34)26-21(36)37-11-12-4-2-1-3-5-12/h1-5,13-14H,6-11H2,(H,24,31)(H,25,35)(H,26,36)(H,27,30)(H,33,34)(H2,22,23,28)/t13-,14?/m0/s1

Standard InChI Key:  NBFKQSDHKHRQMI-LSLKUGRBSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
    1.9375   -1.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625   -2.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -2.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875   -1.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583   -2.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1875   -2.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -3.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5750   -2.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -2.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7375   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750   -1.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -1.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -3.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -3.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -3.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -3.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7958   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2208   -1.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -4.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7125   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3250   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3750   -4.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1542   -4.5500    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 22  1  0
  5  8  1  1
  9 11  1  0
 10  7  1  0
 11  7  1  0
 12  6  2  0
 13  1  1  0
 14  8  1  0
 15 13  1  0
 16  6  1  0
 17 20  1  0
 18  2  2  0
 19  3  2  0
 20 14  1  0
 21 15  1  0
 22 21  1  0
 23 10  1  0
 24  9  2  0
 25 10  2  0
 26  9  1  0
 27 14  2  0
 28 15  2  0
 29 26  1  0
 30 29  1  0
 31 12  1  0
 32 16  1  0
 33 30  2  0
 34 30  1  0
 35 34  2  0
 36 33  1  0
 37 35  1  0
  5  4  1  0
 32 31  1  0
 36 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160226

   3-[[2-[(4S)-4-[2-[2-(4,5-dihydro-1H-imidazol-2-yl)hydrazinyl]-2-oxoethyl]-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: 518.49

Molecular Weight (Monoisotopic): 518.1874

AlogP: -2.63

#Rotatable Bonds: 10

Polar Surface Area: 219.66

Molecular Species: ZWITTERION

HBA: 10

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.42

CX Basic pKa: 9.75

CX LogP: -4.20

CX LogD: -4.20

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.13

Np Likeness Score: -0.80

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