Pyrrolidine-2-carboxylic acid [1-(carbamoylmethyl-carbamoyl)-2-(4-nitro-phenyl)-ethyl]-amide

ID: ALA2372912

PubChem CID: 14603770

Max Phase: Preclinical

Molecular Formula: C16H21N5O5

Molecular Weight: 363.37

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NC(=O)CNC(=O)[C@H](Cc1ccc([N+](=O)[O-])cc1)NC(=O)[C@@H]1CCCN1

Standard InChI:  InChI=1S/C16H21N5O5/c17-14(22)9-19-15(23)13(20-16(24)12-2-1-7-18-12)8-10-3-5-11(6-4-10)21(25)26/h3-6,12-13,18H,1-2,7-9H2,(H2,17,22)(H,19,23)(H,20,24)/t12-,13-/m0/s1

Standard InChI Key:  OQEIVYKPSALGDF-STQMWFEESA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.5763   -2.7103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4756    0.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750    0.8326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5988    0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994    0.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1633   -2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3315    0.4871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7852   -2.4897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7596    0.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -3.5013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100    0.4247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511    0.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005   -0.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9327   -0.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5738    1.7069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7845   -0.2873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9710   -2.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510   -1.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0352    0.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3456   -0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4590    0.9700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497   -1.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5463   -0.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397    1.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6387    1.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269    1.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  5  1  0
  4  5  1  0
  5 14  1  6
  6  1  1  0
  7  4  1  0
  8  1  1  0
  9 19  1  0
 10  1  2  0
 11 12  1  0
 12  2  1  1
 13  2  2  0
 14 20  1  0
 15  4  2  0
 16  9  2  0
 17  6  1  0
 18  6  2  0
 19  7  1  0
 20 23  2  0
 21  9  1  0
 22 17  2  0
 23 18  1  0
 24 11  1  0
 25 12  1  0
 26 25  1  0
 22 20  1  0
 26 24  1  0
M  CHG  2   1   1   8  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2372912

   H-Pro-Phe(4-NO2)-Gly-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: 363.37

Molecular Weight (Monoisotopic): 363.1543

AlogP: -1.02

#Rotatable Bonds: 8

Polar Surface Area: 156.46

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.70

CX Basic pKa: 9.50

CX LogP: -0.95

CX LogD: -3.03

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.34

Np Likeness Score: -0.76

References

1. Johnson RL, Bontems RJ, Yang KE, Mishra RK..  (1990)  Synthesis and biological evaluation of analogues of Pro-Leu-Gly-NH2 modified at the leucyl residue.,  33  (6): [PMID:1971310] [10.1021/jm00168a045]

Source

Source(1):

• Scientific Literature