2-{2-[2-(2-Acetylamino-5-guanidino-pentanoylamino)-3-hydroxy-propionylamino]-3-methyl-butyrylamino}-pentanedioic acid diamide

ID: ALA264393

PubChem CID: 14999601

Max Phase: Preclinical

Molecular Formula: C21H39N9O7

Molecular Weight: 529.60

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(N)=O)C(C)C

Standard InChI:  InChI=1S/C21H39N9O7/c1-10(2)16(20(37)28-12(17(23)34)6-7-15(22)33)30-19(36)14(9-31)29-18(35)13(27-11(3)32)5-4-8-26-21(24)25/h10,12-14,16,31H,4-9H2,1-3H3,(H2,22,33)(H2,23,34)(H,27,32)(H,28,37)(H,29,35)(H,30,36)(H4,24,25,26)/t12-,13-,14-,16-/m0/s1

Standard InChI Key:  FVFQLPZSQIZAFV-YXWQFLTLSA-N

Molfile:  

     RDKit          2D

 37 36  0  0  1  0  0  0  0  0999 V2000
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    9.4042   -5.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4667   -6.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -6.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.6292   -3.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2917   -8.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875   -9.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6292   -5.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1042   -7.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9292   -4.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2250   -3.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7000   -4.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -5.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -7.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875   -8.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4042   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8125   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  3  1  0
  7  1  1  0
  8  1  1  0
  9 24  2  0
 10 12  1  0
 11 14  1  0
 12  8  1  0
 13 11  1  0
 14  4  1  0
 15 28  1  0
 16  9  1  0
 17  1  2  0
 18  3  2  0
 19  4  2  0
 20 10  2  0
 21 13  2  0
 22 15  2  0
 12 23  1  1
 24 34  1  0
 25  9  1  0
 26 10  1  0
  7 27  1  6
 28 23  1  0
 29 15  1  0
  6 30  1  1
 31 30  1  0
 32 13  1  0
 14 33  1  6
 34 37  1  0
 35 27  1  0
 36 27  1  0
 37 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA264393

   Ac-Arg-Ser-Val-Gln-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: 529.60

Molecular Weight (Monoisotopic): 529.2972

AlogP: -4.60

#Rotatable Bonds: 17

Polar Surface Area: 287.21

Molecular Species: BASE

HBA: 8

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.72

CX Basic pKa: 15.83

CX LogP: -5.75

CX LogD: -7.84

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.05

Np Likeness Score: 0.42

References

1. Deshpande MS, Burton J..  (1992)  Mapping the binding site of tissue kallikrein: preparation and testing of all possible substrate analog inhibitors homologous with the sequence of kininogen between Ser386 and Gln392.,  35  (17): [PMID:1507198] [10.1021/jm00095a002]

Source

Source(1):

• Scientific Literature