2-((S)-3-((S)-2-Amino-4-methylpentanamido)-2,6-dioxopiperidin-1-yl)acetic acid hydrochloride

ID: ALA1098906

PubChem CID: 44481668

Max Phase: Preclinical

Molecular Formula: C13H22ClN3O5

Molecular Weight: 299.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](N)C(=O)N[C@H]1CCC(=O)N(CC(=O)O)C1=O.Cl

Standard InChI:  InChI=1S/C13H21N3O5.ClH/c1-7(2)5-8(14)12(20)15-9-3-4-10(17)16(13(9)21)6-11(18)19;/h7-9H,3-6,14H2,1-2H3,(H,15,20)(H,18,19);1H/t8-,9-;/m0./s1

Standard InChI Key:  QZHNPJMIVATDBF-OZZZDHQUSA-N

Molfile:  

     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
   16.8166   -3.2952    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5702   -4.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2859   -3.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8543   -3.7892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0017   -4.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2859   -2.9632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7176   -3.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4283   -4.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1378   -3.7941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1420   -2.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4305   -2.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7107   -2.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4254   -5.0274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8594   -2.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8521   -4.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5694   -3.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2836   -4.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5725   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5702   -5.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -5.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -6.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1468   -5.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  8 13  2  0
  7  5  1  1
 10 14  2  0
  7  8  1  0
  9 15  1  0
  2  4  1  6
 15 16  1  0
 16 17  1  0
  3  5  1  0
 16 18  2  0
  2  3  1  0
  2 19  1  0
  3  6  2  0
 19 20  1  0
  7 12  1  0
 20 21  1  0
  8  9  1  0
 20 22  1  0
  9 10  1  0
 10 11  1  0
M  END

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: 299.33

Molecular Weight (Monoisotopic): 299.1481

AlogP: -0.92

#Rotatable Bonds: 6

Polar Surface Area: 129.80

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.28

CX Basic pKa: 8.13

CX LogP: -3.37

CX LogD: -3.44

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.54

Np Likeness Score: 0.00

References

1. Li Q, Fang H, Wang X, Xu W..  (2010)  Novel cyclic-imide peptidomimetics as aminopeptidase N inhibitors. Structure-based design, chemistry and activity evaluation. II.,  45  (4): [PMID:20129718] [10.1016/j.ejmech.2009.12.071]

2. Chen, H H, Noble, F F, Roques, B P BP and Fournié-Zaluski, M C MC.  2001-10-11  Long lasting antinociceptive properties of enkephalin degrading enzyme (NEP and APN) inhibitor prodrugs.  [PMID:11585456]

3. Vassiliou, Stamatia S and 7 more authors.  2014-10-09  Structure-guided, single-point modifications in the phosphinic dipeptide structure yield highly potent and selective inhibitors of neutral aminopeptidases.  [PMID:25192493]

4. Węglarz-Tomczak, Ewelina and 5 more authors.  2016-07-19  A structural insight into the P1S1 binding mode of diaminoethylphosphonic and phosphinic acids, selective inhibitors of alanine aminopeptidases.  [PMID:27100031]

5. Singh, Rohit R, Williams, Jessica J and Vince, Robert R.  2017-10-20  Puromycin based inhibitors of aminopeptidases for the potential treatment of hematologic malignancies.  [PMID:28803047]

6. Pascual, Isel and 10 more authors.  2017-11  Discovery of novel non-competitive inhibitors of mammalian neutral M1 aminopeptidase (APN).  [PMID:28964831]

Source

Source(1):

• Scientific Literature