(S)-1-((S)-3-(4-hydroxyphenyl)-2-((S)-5-oxopyrrolidine-2-carboxamido)propanoyl)pyrrolidine-2-carboxamide

ID: ALA3953573

PubChem CID: 9952229

Max Phase: Preclinical

Molecular Formula: C19H24N4O5

Molecular Weight: 388.42

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H]1CCC(=O)N1

Standard InChI:  InChI=1S/C19H24N4O5/c20-17(26)15-2-1-9-23(15)19(28)14(10-11-3-5-12(24)6-4-11)22-18(27)13-7-8-16(25)21-13/h3-6,13-15,24H,1-2,7-10H2,(H2,20,26)(H,21,25)(H,22,27)/t13-,14-,15-/m0/s1

Standard InChI Key:  QFMGVKYIXZPFFF-KKUMJFAQSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    8.0541  -15.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7686  -15.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4830  -15.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1976  -15.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4830  -16.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0541  -16.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3397  -16.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7686  -16.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5864  -16.6071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0344  -17.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4469  -17.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2538  -17.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2138  -17.1340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7686  -14.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9513  -15.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5034  -15.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0908  -14.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2839  -14.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1251  -16.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5135  -16.9783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9104  -16.6773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0541  -14.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0569  -13.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3433  -12.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278  -13.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6305  -14.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3447  -14.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9129  -12.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  0
  7  6  1  6
  6  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  7  1  0
 10 13  2  0
  2 14  1  1
  4 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  4  1  0
 15 19  1  1
 19 20  1  0
 19 21  2  0
 14 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3953573

   Pyroglutamyltyrosylprolineamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 388.42

Molecular Weight (Monoisotopic): 388.1747

AlogP: -0.83

#Rotatable Bonds: 6

Polar Surface Area: 141.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: -1.14

CX LogD: -1.15

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -0.18

References

1.  (2010)  TRH-like peptide derivatives as inhibitors of the TRH-degrading ectoenzyme, 

Source

Source(1):

• Patent Bioactivity Data