N-(N-(4-azidobenzoyl)aminoethyl)-3(R)-[(2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide hydrochloride

ID: ALA541131

PubChem CID: 11670161

Max Phase: Preclinical

Molecular Formula: C20H27ClN8O4

Molecular Weight: 442.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.[N-]=[N+]=Nc1ccc(C(=O)NCCNC(=O)CN2CC[C@@H](NC(=O)[C@@H]3CCCN3)C2=O)cc1

Standard InChI:  InChI=1S/C20H26N8O4.ClH/c21-27-26-14-5-3-13(4-6-14)18(30)24-10-9-23-17(29)12-28-11-7-16(20(28)32)25-19(31)15-2-1-8-22-15;/h3-6,15-16,22H,1-2,7-12H2,(H,23,29)(H,24,30)(H,25,31);1H/t15-,16+;/m0./s1

Standard InChI Key:  JERCAYCPOIAGQN-IDVLALEDSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    1.1832   -3.1500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909   -0.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452    0.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6756    0.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836    0.0629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885    1.3114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5078    0.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7531    0.5088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444    1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6549    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648    0.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5932    0.8504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1123    1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3701    1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5897    2.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3500    1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2918    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8518    2.2372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8890    0.7899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    0.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8123    0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332    0.4420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2411    0.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9619    0.4197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2283   -0.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -1.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945   -2.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2029   -2.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9262   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9358   -1.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912   -3.2790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -4.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -4.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
 13 17  1  1
  4  5  1  0
 17 19  1  0
 11 19  1  6
  8  9  1  0
  5 20  1  0
  9 10  1  0
 20 21  1  0
 10 11  1  0
 21 22  1  0
 11  7  1  0
 22 23  1  0
 23 24  2  0
  4  6  2  0
 23 25  1  0
  7  8  1  0
 25 26  2  0
  8  3  1  0
 26 27  1  0
 27 28  2  0
  3  4  1  0
 28 29  1  0
  7  2  2  0
 29 30  2  0
 30 25  1  0
 13 12  1  0
 28 31  1  0
 12 14  1  0
 31 32  2  0
 13 15  1  0
 32 33  2  0
 14 16  1  0
 15 16  1  0
M  CHG  2  32   1  33  -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: 442.48

Molecular Weight (Monoisotopic): 442.2077

AlogP: -0.06

#Rotatable Bonds: 9

Polar Surface Area: 168.40

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -10.66

CX Basic pKa: 9.50

CX LogP: -1.27

CX LogD: -3.46

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.18

Np Likeness Score: -0.93

References

1. Fisher A, Mann A, Verma V, Thomas N, Mishra RK, Johnson RL..  (2006)  Design and synthesis of photoaffinity-labeling ligands of the L-prolyl-L-leucylglycinamide binding site involved in the allosteric modulation of the dopamine receptor.,  49  (1): [PMID:16392815] [10.1021/jm050644n]

Source

Source(1):

• Scientific Literature