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

ID: ALA1160224

PubChem CID: 44296762

Max Phase: Preclinical

Molecular Formula: C22H29N7O7

Molecular Weight: 503.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)N[C@@H](CCCNC2=NCCN2)C1=O)NCC(NC(=O)OCc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C22H29N7O7/c30-17(26-11-16(19(32)33)28-22(35)36-13-14-5-2-1-3-6-14)12-29-18(31)15(27-21(29)34)7-4-8-23-20-24-9-10-25-20/h1-3,5-6,15-16H,4,7-13H2,(H,26,30)(H,27,34)(H,28,35)(H,32,33)(H2,23,24,25)/t15-,16?/m0/s1

Standard InChI Key:  UBHFWAZLXVPXAK-VYRBHSGPSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
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    0.9667   -2.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -1.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -2.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6208   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6167   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3833   -2.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -3.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -0.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4417   -3.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5917   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -3.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9333   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0292   -4.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9917   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6042   -3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292   -4.6125    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 24  1  0
  6  3  1  0
  7 18  1  0
  8 10  1  0
  9  7  1  0
 10  7  1  0
 11  5  2  0
 12  1  1  0
 13 12  1  0
 14  5  1  0
 15  2  2  0
 16  3  2  0
 17 13  1  0
 18 17  1  0
 19  9  1  0
 20  8  2  0
 21  9  2  0
 22  8  1  0
 23 13  2  0
 24 30  1  0
 25 22  1  0
 26 25  1  0
 27 11  1  0
  6 28  1  1
 29 14  1  0
 30 33  1  0
 31 26  2  0
 32 26  1  0
 33 28  1  0
 34 31  1  0
 35 32  2  0
 36 35  1  0
  6  4  1  0
 27 29  1  0
 34 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160224

   3-[[2-[(4S)-4-[3-(4,5-dihydro-1H-imidazol-2-ylamino)propyl]-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: 503.52

Molecular Weight (Monoisotopic): 503.2128

AlogP: -1.27

#Rotatable Bonds: 12

Polar Surface Area: 190.56

Molecular Species: ZWITTERION

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.42

CX Basic pKa: 11.04

CX LogP: -2.93

CX LogD: -2.93

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.15

Np Likeness Score: -0.65

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