2-{2-[2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-acetylamino]-3-hydroxy-propionylamino}-5-guanidino-pentanoic acid amide

ID: ALA3144155

PubChem CID: 10650317

Max Phase: Preclinical

Molecular Formula: C23H34N8O6S

Molecular Weight: 550.64

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CN(C)c1cccc2c(S(=O)(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(N)=O)cccc12

Standard InChI:  InChI=1S/C23H34N8O6S/c1-31(2)18-9-3-7-15-14(18)6-4-10-19(15)38(36,37)28-12-20(33)29-17(13-32)22(35)30-16(21(24)34)8-5-11-27-23(25)26/h3-4,6-7,9-10,16-17,28,32H,5,8,11-13H2,1-2H3,(H2,24,34)(H,29,33)(H,30,35)(H4,25,26,27)/t16-,17-/m0/s1

Standard InChI Key:  GNATZFCGYXHMGY-IRXDYDNUSA-N

Molfile:  

     RDKit          2D

 38 39  0  0  0  0  0  0  0  0999 V2000
    4.2891   -7.0653    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747   -6.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5760   -7.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8602   -7.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1457   -6.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8615   -7.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -7.4778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2904   -7.4778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -7.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5773   -7.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1470   -7.0653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0049   -6.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4325   -7.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7181   -7.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7016   -6.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8766   -7.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0049   -7.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5773   -8.3028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168   -6.6528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5760   -6.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7194   -5.8278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4325   -8.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8628   -7.0653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2917   -7.0653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2904   -5.8278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8615   -8.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1457   -5.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8602   -7.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747   -5.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -7.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1470   -8.7153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8602   -5.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1457   -8.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023   -7.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7168   -5.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7194   -7.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1483   -7.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4338   -7.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  2  1  0
  5  4  1  0
  6 11  1  0
  7  1  1  0
  8  3  1  0
  9  5  2  0
 10 23  2  0
 11 13  1  0
 12 17  1  0
 13 14  1  0
 14  7  1  0
 15  1  2  0
 16  1  2  0
 17  8  1  0
 18 10  1  0
 19  9  1  0
 20  3  2  0
 21 12  2  0
 22 13  2  0
 23 37  1  0
 24 10  1  0
 25 12  1  0
  6 26  1  6
 27 32  2  0
 28  4  2  0
 29  2  2  0
 30 33  2  0
 31 26  1  0
 32 29  1  0
 33 28  1  0
 34 19  1  0
 35 19  1  0
 17 36  1  6
 37 38  1  0
 38 36  1  0
  5 27  1  0
 30  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3144155

   Dan-Gly-Ser-Arg-NH2

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: 550.64

Molecular Weight (Monoisotopic): 550.2322

AlogP: -2.32

#Rotatable Bonds: 14

Polar Surface Area: 235.33

Molecular Species: BASE

HBA: 8

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.84

CX Basic pKa: 10.90

CX LogP: -3.00

CX LogD: -4.74

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.08

Np Likeness Score: -0.42

References

1. Prokai L, Prokai-Tatrai K, Zharikova A, Li X, Rocca JR..  (2001)  Combinatorial lead optimization of a neuropeptide FF antagonist.,  44  (10): [PMID:11334572] [10.1021/jm000512o]

Source

Source(1):

• Scientific Literature