N-(N-(4-azido-2-hydroxy-5-iodobenzoyl)aminoethyl)-3(R)-[(2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide hydrochloride

ID: ALA540878

PubChem CID: 11549034

Max Phase: Preclinical

Molecular Formula: C20H26ClIN8O5

Molecular Weight: 584.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.[N-]=[N+]=Nc1cc(O)c(C(=O)NCCNC(=O)CN2CC[C@@H](NC(=O)[C@@H]3CCCN3)C2=O)cc1I

Standard InChI:  InChI=1S/C20H25IN8O5.ClH/c21-12-8-11(16(30)9-15(12)27-28-22)18(32)25-6-5-24-17(31)10-29-7-3-14(20(29)34)26-19(33)13-2-1-4-23-13;/h8-9,13-14,23,30H,1-7,10H2,(H,24,31)(H,25,32)(H,26,33);1H/t13-,14+;/m0./s1

Standard InChI Key:  YZYMNJGOZIGDMD-LMRHVHIWSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
   22.4991   -0.1013    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.2991   -2.5226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4003   -1.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0990   -0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8003   -1.4887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0969    0.4636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0525   -1.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6990   -0.7319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8317    0.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2978    1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0523   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3814   -3.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6486   -1.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8475   -2.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6267   -0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9991   -1.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1558   -1.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4521   -2.7264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5426   -0.3845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -1.4932    0.0000 C   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
    2.6003   -1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024   -2.6977    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
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 I   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
  5 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 25 30  1  0
 29 30  2  0
 28 31  1  0
 31 32  2  0
 32 33  2  0
 30 34  1  0
 27 35  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: 584.38

Molecular Weight (Monoisotopic): 584.0993

AlogP: 0.25

#Rotatable Bonds: 9

Polar Surface Area: 188.63

Molecular Species: ZWITTERION

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -10.72

CX Basic pKa: 9.50

CX LogP: -3.35

CX LogD: -1.32

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.09

Np Likeness Score: -0.79

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