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

ID: ALA1099247

PubChem CID: 44481943

Max Phase: Preclinical

Molecular Formula: C13H23ClN4O5

Molecular Weight: 314.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](C)[C@H](N)C(=O)N[C@H]1CCC(=O)N(CC(=O)NO)C1=O.Cl

Standard InChI:  InChI=1S/C13H22N4O5.ClH/c1-3-7(2)11(14)12(20)15-8-4-5-10(19)17(13(8)21)6-9(18)16-22;/h7-8,11,22H,3-6,14H2,1-2H3,(H,15,20)(H,16,18);1H/t7-,8+,11+;/m1./s1

Standard InChI Key:  GCQLJBNZHASCMY-YTMBMSNTSA-N

Molfile:  

     RDKit          2D

 23 22  0  0  0  0  0  0  0  0999 V2000
    5.3011  -11.0506    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949  -11.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789  -11.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2108  -11.2581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629  -11.6691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789  -10.4320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3470  -11.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3639  -11.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0737  -11.2632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779  -10.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3662  -10.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538  -10.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611  -12.4967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7954  -10.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880  -11.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5056  -11.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200  -11.6822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5087  -10.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949  -12.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067  -12.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831  -12.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831  -13.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324  -11.2721    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  1
  7 12  1  0
 19 21  1  0
  8  9  1  0
 21 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: 8.10

CX LogP: -2.31

CX LogD: -2.71

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.27

Np Likeness Score: -0.20

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