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

ID: ALA1160216

PubChem CID: 44296684

Max Phase: Preclinical

Molecular Formula: C20H28N8O6

Molecular Weight: 476.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@@H]1NC(=O)N(CC(=O)NCC(NC(=O)NCc2ccccc2)C(=O)O)C1=O

Standard InChI:  InChI=1S/C20H28N8O6/c21-18(22)23-8-4-7-13-16(30)28(20(34)27-13)11-15(29)24-10-14(17(31)32)26-19(33)25-9-12-5-2-1-3-6-12/h1-3,5-6,13-14H,4,7-11H2,(H,24,29)(H,27,34)(H,31,32)(H4,21,22,23)(H2,25,26,33)/t13-,14?/m0/s1

Standard InChI Key:  ISWJDGGFQKBKKH-LSLKUGRBSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  1  0  0  0  0  0999 V2000
    2.8792   -1.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -2.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -2.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583   -1.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -0.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4667   -3.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -1.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -1.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292   -1.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0167   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -2.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -2.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833   -2.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2542   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8667   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6542   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3167   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2667   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0917   -4.4250    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 18  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  7  1  0
 17 12  1  0
 18 17  1  0
 19  8  1  0
 20  7  2  0
 21  8  2  0
 22 12  2  0
 23 28  1  0
 24 11  1  0
 25 16  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:

   

   ALA1160216

   2-(benzylcarbamoylamino)-3-[[2-[(4S)-4-[3-(diaminomethylideneamino)propyl]-2,5-dioxoimidazolidin-1-yl]acetyl]amino]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: 476.49

Molecular Weight (Monoisotopic): 476.2132

AlogP: -1.76

#Rotatable Bonds: 12

Polar Surface Area: 218.84

Molecular Species: ZWITTERION

HBA: 6

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.52

CX Basic pKa: 12.17

CX LogP: -3.99

CX LogD: -3.99

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.07

Np Likeness Score: -0.79

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