(S)-2-Amino-N-((S)-1-(2-(hydroxyamino)-2-oxoethyl)-2,6-dioxopiperidin-3-yl)-4-methylpentanamide hydrochloride

ID: ALA1098910

PubChem CID: 44481940

Max Phase: Preclinical

Molecular Formula: C13H23ClN4O5

Molecular Weight: 314.34

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)NO)C1=O.Cl

Standard InChI:  InChI=1S/C13H22N4O5.ClH/c1-7(2)5-8(14)12(20)15-9-3-4-11(19)17(13(9)21)6-10(18)16-22;/h7-9,22H,3-6,14H2,1-2H3,(H,15,20)(H,16,18);1H/t8-,9-;/m0./s1

Standard InChI Key:  GNKXQPZISNRNHG-OZZZDHQUSA-N

Molfile:  

     RDKit          2D

 23 22  0  0  0  0  0  0  0  0999 V2000
   16.7086   -4.7366    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4602   -5.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1761   -5.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7442   -5.2305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8921   -5.6415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1761   -4.4044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6081   -5.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3191   -5.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0287   -5.2356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0329   -4.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3213   -3.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6012   -4.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3161   -6.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7504   -3.9967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7432   -5.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4607   -5.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1750   -5.6547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4638   -4.4149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4602   -6.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7484   -6.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7484   -7.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0365   -6.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8874   -5.2446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 17 23  1  0
 10 11  1  0
 11 12  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: 314.34

Molecular Weight (Monoisotopic): 314.1590

AlogP: -1.50

#Rotatable Bonds: 6

Polar Surface Area: 141.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.75

CX Basic pKa: 8.04

CX LogP: -2.35

CX LogD: -2.73

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.27

Np Likeness Score: -0.12

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