3-{2-[(S)-4-(3-Guanidino-propyl)-2,5-dioxo-imidazolidin-1-yl]-acetylamino}-2-[(naphthalene-2-carbonyl)-amino]-propionic acid anion

ID: ALA1160229

PubChem CID: 44296892

Max Phase: Preclinical

Molecular Formula: C23H27N7O6

Molecular Weight: 497.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@@H]1NC(=O)N(CC(=O)NCC(NC(=O)c2ccc3ccccc3c2)C(=O)O)C1=O

Standard InChI:  InChI=1S/C23H27N7O6/c24-22(25)26-9-3-6-16-20(33)30(23(36)29-16)12-18(31)27-11-17(21(34)35)28-19(32)15-8-7-13-4-1-2-5-14(13)10-15/h1-2,4-5,7-8,10,16-17H,3,6,9,11-12H2,(H,27,31)(H,28,32)(H,29,36)(H,34,35)(H4,24,25,26)/t16-,17?/m0/s1

Standard InChI Key:  NALFUKWGEKEECL-BHWOMJMDSA-N

Molfile:  

     RDKit          2D

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    1.1542   -1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7875   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375   -2.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5417    0.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -1.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2292   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4500   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1583   -1.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8500   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7917   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  7  1  0
  6 19  1  0
  7  6  1  0
  8  3  1  0
  9  6  1  0
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 11 26  1  0
 12  5  1  0
 13 10  1  0
 14 12  1  0
 15  2  2  0
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 17  3  2  0
 18 13  1  0
 19 18  1  0
 20 14  2  0
 21  9  1  0
 22  5  2  0
 23  9  2  0
 24 12  2  0
 25 13  2  0
 26 32  1  0
 27 28  2  0
 28 24  1  0
 29 11  1  0
  8 30  1  1
 31 20  1  0
 32 34  1  0
 33 27  1  0
 34 30  1  0
 35 31  2  0
 36 33  2  0
  8  4  1  0
 20 27  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160229

   3-[[2-[(4S)-4-[3-(diaminomethylideneamino)propyl]-2,5-dioxoimidazolidin-1-yl]acetyl]amino]-2-(naphthalene-2-carbonylamino)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: 497.51

Molecular Weight (Monoisotopic): 497.2023

AlogP: -0.68

#Rotatable Bonds: 11

Polar Surface Area: 206.81

Molecular Species: ZWITTERION

HBA: 6

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.50

CX Basic pKa: 12.17

CX LogP: -2.76

CX LogD: -2.76

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.09

Np Likeness Score: -0.57

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