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

ID: ALA541634

PubChem CID: 11546890

Max Phase: Preclinical

Molecular Formula: C18H23ClN8O4

Molecular Weight: 414.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.[N-]=[N+]=Nc1ccc(C(=O)N[C@H]2CN[C@H](C(=O)N[C@@H]3CCN(CC(N)=O)C3=O)C2)cc1

Standard InChI:  InChI=1S/C18H22N8O4.ClH/c19-15(27)9-26-6-5-13(18(26)30)23-17(29)14-7-12(8-21-14)22-16(28)10-1-3-11(4-2-10)24-25-20;/h1-4,12-14,21H,5-9H2,(H2,19,27)(H,22,28)(H,23,29);1H/t12-,13-,14+;/m1./s1

Standard InChI Key:  RIRGPIBNSMEHPY-NNNATCHMSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   12.5356   -6.3973    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1740   -8.9887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7396  -12.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7374  -13.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6971  -14.1395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7754  -14.1436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2870   -9.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4437  -11.2887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0734  -11.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0697  -10.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8286   -9.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2484   -4.2507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2447   -3.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1050   -6.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2982   -7.0472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2210   -8.1326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9374    0.1440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  2  7  2  0
  3  8  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 10 11  1  0
 12 13  1  0
 12 14  1  0
 13 15  1  0
 14 16  1  0
 15 16  1  0
 13 17  1  6
 17 18  2  0
 11 19  1  1
 17 19  1  0
 16 20  1  1
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 23 28  1  0
 27 28  2  0
 26 29  1  0
 29 30  2  0
 30 31  2  0
M  CHG  2  30   1  31  -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: 414.43

Molecular Weight (Monoisotopic): 414.1764

AlogP: -0.71

#Rotatable Bonds: 7

Polar Surface Area: 182.39

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -10.63

CX Basic pKa: 8.64

CX LogP: -1.95

CX LogD: -3.33

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: -0.80

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