ethyl 2-((S)-1-((S)-2-((S)-1-acetylpyrrolidine-2-carboxamido)propanoyl)pyrrolidine-2-carbonyl)hydrazinecarboxylate

ID: ALA3272359

PubChem CID: 90677661

Max Phase: Preclinical

Molecular Formula: C18H29N5O6

Molecular Weight: 411.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)NNC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(C)=O

Standard InChI:  InChI=1S/C18H29N5O6/c1-4-29-18(28)21-20-16(26)14-8-6-10-23(14)17(27)11(2)19-15(25)13-7-5-9-22(13)12(3)24/h11,13-14H,4-10H2,1-3H3,(H,19,25)(H,20,26)(H,21,28)/t11-,13-,14-/m0/s1

Standard InChI Key:  HHBAWUXHCAQVDM-UBHSHLNASA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   11.2680   -2.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3980   -3.6659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8900   -4.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2032   -4.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2861   -4.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8612   -5.7564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1458   -6.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2701   -3.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6303   -3.7579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7135   -6.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4550   -5.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6989   -3.2557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9976   -3.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9976   -4.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0083   -3.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1013   -2.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1013   -3.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3962   -2.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5017   -3.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7474   -6.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8026   -3.6659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6056   -4.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2011   -3.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9918   -7.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1232   -6.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4063   -7.3236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5331   -8.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3284   -8.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6930   -7.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 22  1  0
  8  1  1  0
  7 11  2  0
 17 21  1  0
 21 19  1  0
 26 10  1  0
 22  9  1  0
 12  2  1  0
 17 16  2  0
  6  3  1  0
 10 20  2  0
  2 17  1  0
 22  5  2  0
 25  7  1  6
 13 14  2  0
 13 12  1  0
 15 18  1  0
  7  6  1  0
 15  9  1  0
  8 13  1  1
 18  1  1  0
  9  8  1  0
  3  4  1  1
 19 23  1  0
 10 24  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3272359

   ethyl N-[[(2S)-1-[(2S)-2-[[(2S)-1-acetylpyrrolidine-2-carbonyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]carbamate

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: 411.46

Molecular Weight (Monoisotopic): 411.2118

AlogP: -0.73

#Rotatable Bonds: 5

Polar Surface Area: 137.15

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.14

CX Basic pKa: ┄

CX LogP: -1.71

CX LogD: -1.71

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -1.04

References

1. Dorn CP, Zimmerman M, Yang SS, Yurewicz EC, Ashe BM, Frankshun R, Jones H..  (1977)  Proteinase inhibitors. I. Inhibitors of elastase.,  20  (11): [PMID:915907] [10.1021/jm00221a020]

Source

Source(1):

• Scientific Literature