2-((S)-3-((S)-2-Amino-3-(4-hydroxyphenyl)propanamido)-2,6-dioxopiperidin-1-yl)acetic acid hydrochloride

ID: ALA1095255

PubChem CID: 44481672

Max Phase: Preclinical

Molecular Formula: C16H20ClN3O6

Molecular Weight: 349.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@H]1CCC(=O)N(CC(=O)O)C1=O

Standard InChI:  InChI=1S/C16H19N3O6.ClH/c17-11(7-9-1-3-10(20)4-2-9)15(24)18-12-5-6-13(21)19(16(12)25)8-14(22)23;/h1-4,11-12,20H,5-8,17H2,(H,18,24)(H,22,23);1H/t11-,12-;/m0./s1

Standard InChI Key:  CRRNFXNWBSGSDS-FXMYHANSSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
    7.3690  -22.3733    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527  -23.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350  -22.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7704  -22.7436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3826  -23.1555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350  -21.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002  -22.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8128  -23.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242  -22.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5284  -21.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8151  -21.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0934  -21.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099  -23.9850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476  -21.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402  -23.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9594  -22.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6755  -23.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625  -21.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527  -23.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662  -24.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782  -23.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1911  -24.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1916  -25.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731  -25.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7630  -25.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9045  -25.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 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  2  0
  8  9  1  0
 21 22  1  0
  9 10  1  0
 22 23  2  0
 10 11  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
  8 13  2  0
  7  5  1  1
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: 349.34

Molecular Weight (Monoisotopic): 349.1274

AlogP: -1.02

#Rotatable Bonds: 6

Polar Surface Area: 150.03

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.62

CX Basic pKa: 7.73

CX LogP: -3.28

CX LogD: -3.43

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.48

Np Likeness Score: 0.11

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