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

ID: ALA1160215

PubChem CID: 44296682

Max Phase: Preclinical

Molecular Formula: C20H28N8O5S

Molecular Weight: 492.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H28N8O5S/c21-18(22)23-8-4-7-13-16(30)28(20(33)27-13)11-15(29)24-10-14(17(31)32)26-19(34)25-9-12-5-2-1-3-6-12/h1-3,5-6,13-14H,4,7-11H2,(H,24,29)(H,27,33)(H,31,32)(H4,21,22,23)(H2,25,26,34)/t13-,14?/m0/s1

Standard InChI Key:  CEYQEAWYRXDCAO-LSLKUGRBSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
    3.4750   -2.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -3.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667   -3.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708   -2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -4.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708   -1.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -1.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6250   -2.4542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0625   -3.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -2.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -1.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -1.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -3.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583   -3.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875   -3.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8500   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4542   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2875   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2417   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9042   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8542   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6875   -5.2042    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 19  1  0
  7  9  2  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  7  1  0
 18 12  1  0
 19 18  1  0
 20  8  1  0
 21  8  2  0
 22 12  2  0
 23 28  1  0
 24 11  1  0
 25 17  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:

   

   ALA1160215

   2-(benzylcarbamothioylamino)-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: 492.56

Molecular Weight (Monoisotopic): 492.1903

AlogP: -1.18

#Rotatable Bonds: 12

Polar Surface Area: 202.10

Molecular Species: ZWITTERION

HBA: 6

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.23

CX Basic pKa: 12.92

CX LogP: -3.40

CX LogD: -3.38

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.06

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