(S)-2-[((S)-Pyrrolidine-2-carbonyl)-amino]-pentanedioic acid 5-amide 1-{[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-4-guanidino-butyl]-amide}

ID: ALA326770

PubChem CID: 10030332

Max Phase: Preclinical

Molecular Formula: C25H39N9O5

Molecular Weight: 545.65

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NC(=O)CC[C@H](NC(=O)[C@@H]1CCCN1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C25H39N9O5/c26-20(35)11-10-18(33-22(37)16-8-4-12-30-16)24(39)32-17(9-5-13-31-25(28)29)23(38)34-19(21(27)36)14-15-6-2-1-3-7-15/h1-3,6-7,16-19,30H,4-5,8-14H2,(H2,26,35)(H2,27,36)(H,32,39)(H,33,37)(H,34,38)(H4,28,29,31)/t16-,17-,18-,19-/m0/s1

Standard InChI Key:  VVKYIUFJEDANQO-VJANTYMQSA-N

Molfile:  

     RDKit          2D

 39 40  0  0  1  0  0  0  0  0999 V2000
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    9.3125   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0167   -3.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -3.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8792   -4.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0167   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7417   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4542   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -6.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3125   -0.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -4.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1667   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3125   -5.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -5.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7417   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4542   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -6.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0167   -1.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7417   -0.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1667   -4.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -6.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3250   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3125   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5000   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250   -6.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3125   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3125   -7.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4792   -7.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  3  5  1  0
  4  2  1  0
 10  5  1  6
  6  1  1  0
  7 23  2  0
  8  4  1  6
  9  8  1  0
 10  1  1  0
 11  6  1  1
 12 26  1  0
 13  7  1  0
 14 15  1  0
 15  3  1  1
 16  1  2  0
 17  2  2  0
 18  3  2  0
  8 19  1  0
 20  9  2  0
 21 12  2  0
 10 22  1  0
 23 31  1  0
 24  7  1  0
 25  9  1  0
 26 22  1  0
 27 12  1  0
 28 19  1  0
 29 14  1  0
 11 30  1  0
 31 35  1  0
 15 32  1  0
 33 28  2  0
 34 28  1  0
 35 30  1  0
 36 32  1  0
 37 34  2  0
 38 33  1  0
 39 37  1  0
 36 29  1  0
 39 38  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA326770

   Neuropeptide FF (5-8)

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 545.65

Molecular Weight (Monoisotopic): 545.3074

AlogP: -2.76

#Rotatable Bonds: 16

Polar Surface Area: 249.91

Molecular Species: BASE

HBA: 7

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.89

CX Basic pKa: 10.80

CX LogP: -3.25

CX LogD: -7.43

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.06

Np Likeness Score: 0.25

References

1. Gicquel S, Mazarguil H, Desprat C, Allard M, Devillers JP, Simonnet G, Zajac JM..  (1994)  Structure-activity study of neuropeptide FF: contribution of N-terminal regions to affinity and activity.,  37  (21): [PMID:7932576] [10.1021/jm00047a005]

2. Nguyen T,Marusich J,Li JX,Zhang Y.  (2020)  Neuropeptide FF and Its Receptors: Therapeutic Applications and Ligand Development.,  63  (21.0): [PMID:32673481] [10.1021/acs.jmedchem.0c00643]

Source

Source(1):

• Scientific Literature