2-Acetylamino-5-guanidino-pentanoic acid (1-carbamoyl-2-hydroxy-ethyl)-amide

ID: ALA104404

PubChem CID: 14999612

Max Phase: Preclinical

Molecular Formula: C11H22N6O4

Molecular Weight: 302.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H22N6O4/c1-6(19)16-7(3-2-4-15-11(13)14)10(21)17-8(5-18)9(12)20/h7-8,18H,2-5H2,1H3,(H2,12,20)(H,16,19)(H,17,21)(H4,13,14,15)/t7-,8-/m0/s1

Standard InChI Key:  PYLIRDMIHCSMPW-YUMQZZPRSA-N

Molfile:  

     RDKit          2D

 21 20  0  0  1  0  0  0  0  0999 V2000
    4.3292   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -3.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -2.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -6.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -5.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -6.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -2.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -1.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -4.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5 13  2  0
  6  8  1  0
  7  6  1  0
  8  1  1  0
  9  5  1  0
 10  1  2  0
 11  4  2  0
 12  7  2  0
 13 20  1  0
 14  5  1  0
 15  4  1  0
  3 16  1  1
 17 16  1  0
 18  7  1  0
  8 19  1  6
 20 21  1  0
 21 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA104404

   (2S)-2-acetamido-N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]-5-(diaminomethylideneamino)pentanamide

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: 302.34

Molecular Weight (Monoisotopic): 302.1703

AlogP: -3.49

#Rotatable Bonds: 9

Polar Surface Area: 185.92

Molecular Species: BASE

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.03

CX Basic pKa: 10.88

CX LogP: -4.39

CX LogD: -6.50

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.15

Np Likeness Score: 0.69

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