2-((S)-3-((S)-2-amino-3-methylbutanamido)-2,6-dioxopiperidin-1-yl)acetic acid hydrochloride

ID: ALA1097596

PubChem CID: 44481667

Max Phase: Preclinical

Molecular Formula: C12H20ClN3O5

Molecular Weight: 285.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H19N3O5.ClH/c1-6(2)10(13)11(19)14-7-3-4-8(16)15(12(7)20)5-9(17)18;/h6-7,10H,3-5,13H2,1-2H3,(H,14,19)(H,17,18);1H/t7-,10-;/m0./s1

Standard InChI Key:  VDZKFIMFLNYPKT-YUWZRIFDSA-N

Molfile:  

     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
    6.1072   -2.8835    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147   -3.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -3.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1302   -3.3191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835   -3.7298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -2.4935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2680   -3.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426   -3.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1519   -3.3242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1562   -2.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4449   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748   -2.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -4.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733   -2.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659   -3.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5831   -3.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2971   -3.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861   -2.5039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147   -4.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261   -4.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7032   -4.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  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
 19 21  1  0
  8  9  1  0
  9 10  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: 285.30

Molecular Weight (Monoisotopic): 285.1325

AlogP: -1.31

#Rotatable Bonds: 5

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: -3.74

CX LogD: -3.79

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.54

Np Likeness Score: -0.15

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