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

ID: ALA1097595

PubChem CID: 44481664

Max Phase: Preclinical

Molecular Formula: C10H16ClN3O5

Molecular Weight: 257.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H15N3O5.ClH/c1-5(11)9(17)12-6-2-3-7(14)13(10(6)18)4-8(15)16;/h5-6H,2-4,11H2,1H3,(H,12,17)(H,15,16);1H/t5-,6-;/m0./s1

Standard InChI Key:  RNLHLQIYGZJXND-GEMLJDPKSA-N

Molfile:  

     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
   16.9597    2.4934    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5629    1.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2784    2.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8474    2.1241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9940    1.7134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2784    2.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7094    2.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4200    1.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1292    2.1191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1335    2.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4223    3.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7026    2.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4170    0.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8506    3.3571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8432    1.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5603    2.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2743    1.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5634    2.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5629    0.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9 10  1  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  0
 15 16  1  0
 16 17  1  0
  3  5  1  0
 16 18  2  0
  2  3  1  0
  2 19  1  6
  3  6  2  0
  7 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: 257.25

Molecular Weight (Monoisotopic): 257.1012

AlogP: -1.95

#Rotatable Bonds: 4

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: 3.38

CX Basic pKa: 8.09

CX LogP: -4.63

CX LogD: -4.70

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.50

Np Likeness Score: -0.36

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