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

ID: ALA1098907

PubChem CID: 44481670

Max Phase: Preclinical

Molecular Formula: C13H22ClN3O5

Molecular Weight: 299.33

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)O)C1=O.Cl

Standard InChI:  InChI=1S/C13H21N3O5.ClH/c1-3-7(2)11(14)12(20)15-8-4-5-9(17)16(13(8)21)6-10(18)19;/h7-8,11H,3-6,14H2,1-2H3,(H,15,20)(H,18,19);1H/t7-,8+,11+;/m1./s1

Standard InChI Key:  ZNIVRXQEENKLLE-YTMBMSNTSA-N

Molfile:  

     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
    5.4118   -9.6077    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822  -10.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664   -9.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980   -9.8152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9506  -10.2261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664   -8.9893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349   -9.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4759  -10.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -9.8202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897   -8.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782   -8.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -8.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730  -11.0535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -8.5817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8997  -10.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170   -9.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3313  -10.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201   -8.9998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822  -11.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0938  -11.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706  -11.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6706  -12.2805    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  1
  7 12  1  0
 19 21  1  0
  8  9  1  0
 21 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: 3.18

CX Basic pKa: 8.21

CX LogP: -3.29

CX LogD: -3.35

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.54

Np Likeness Score: -0.09

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