ethyl 2-((S)-1-((S)-2-((S)-2-acetamidopropanamido)propanoyl)pyrrolidine-2-carbonyl)hydrazinecarboxylate

ID: ALA3272695

PubChem CID: 90677660

Max Phase: Preclinical

Molecular Formula: C16H27N5O6

Molecular Weight: 385.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H27N5O6/c1-5-27-16(26)20-19-14(24)12-7-6-8-21(12)15(25)10(3)18-13(23)9(2)17-11(4)22/h9-10,12H,5-8H2,1-4H3,(H,17,22)(H,18,23)(H,19,24)(H,20,26)/t9-,10-,12-/m0/s1

Standard InChI Key:  KFKNRAGFNFQUID-NHCYSSNCSA-N

Molfile:  

     RDKit          2D

 27 27  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
    9.1213   -6.9539    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
    9.8128   -7.3893    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
  3 22  1  0
  8  1  1  0
  7 11  2  0
 17 21  1  0
 21 19  1  0
 25 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
 24  7  1  0
 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
 24 25  1  0
 24 26  1  6
 10 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3272695

   ethyl N-[[(2S)-1-[(2S)-2-[[(2S)-2-acetamidopropanoyl]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: 385.42

Molecular Weight (Monoisotopic): 385.1961

AlogP: -1.22

#Rotatable Bonds: 6

Polar Surface Area: 145.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.30

CX Basic pKa: ┄

CX LogP: -1.98

CX LogD: -1.98

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -1.12

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