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

ID: ALA1160225

PubChem CID: 44296797

Max Phase: Preclinical

Molecular Formula: C23H27N7O7

Molecular Weight: 513.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)N[C@@H](CCCNc2ncccn2)C1=O)NCC(NC(=O)OCc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C23H27N7O7/c31-18(27-12-17(20(33)34)29-23(36)37-14-15-6-2-1-3-7-15)13-30-19(32)16(28-22(30)35)8-4-9-24-21-25-10-5-11-26-21/h1-3,5-7,10-11,16-17H,4,8-9,12-14H2,(H,27,31)(H,28,35)(H,29,36)(H,33,34)(H,24,25,26)/t16-,17?/m0/s1

Standard InChI Key:  LSRGWAWHLWBSEJ-BHWOMJMDSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
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    2.4917   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -1.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3250   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9750   -1.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958    0.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -1.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667    0.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -0.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3375   -1.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -1.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -0.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250   -1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7375   -1.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5250    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208   -0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5167   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5625   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1292   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1792   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9542   -2.9750    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 24  1  0
 12 10  1  0
 13  2  2  0
 14 11  2  0
 15 11  1  0
 16  3  2  0
 17 12  1  0
 18 17  1  0
 19  8  1  0
 20  7  2  0
 21  8  2  0
 22  7  1  0
 23 12  2  0
 24 31  1  0
 25 22  1  0
 26 25  1  0
 27 29  1  0
  5 28  1  1
 29 15  2  0
 30 14  1  0
 31 34  1  0
 32 26  1  0
 33 26  2  0
 34 28  1  0
 35 32  2  0
 36 33  1  0
 37 36  2  0
  5  4  1  0
 30 27  2  0
 35 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160225

   3-[[2-[(4S)-2,5-dioxo-4-[3-(pyrimidin-2-ylamino)propyl]imidazolidin-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: 513.51

Molecular Weight (Monoisotopic): 513.1972

AlogP: 0.08

#Rotatable Bonds: 13

Polar Surface Area: 191.95

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.38

CX Basic pKa: 4.47

CX LogP: -1.12

CX LogD: -3.85

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.18

Np Likeness Score: -0.98

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