N1-((S)-2-((S)-3-hydroxypyrrolidin-1-yl)-1-phenylethyl)-N1-methyl-N4-(thiazol-2-yl)succinamide

ID: ALA397475

PubChem CID: 11304200

Max Phase: Preclinical

Molecular Formula: C20H26N4O3S

Molecular Weight: 402.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C(=O)CCC(=O)Nc1nccs1)[C@H](CN1CC[C@H](O)C1)c1ccccc1

Standard InChI:  InChI=1S/C20H26N4O3S/c1-23(19(27)8-7-18(26)22-20-21-10-12-28-20)17(15-5-3-2-4-6-15)14-24-11-9-16(25)13-24/h2-6,10,12,16-17,25H,7-9,11,13-14H2,1H3,(H,21,22,26)/t16-,17+/m0/s1

Standard InChI Key:  USGVMHCKEFUUML-DLBZAZTESA-N

Molfile:  

     RDKit          2D

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   10.4557  -16.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1706  -16.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8870  -16.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8841  -15.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1688  -15.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1704  -17.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4558  -18.2025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4556  -19.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7414  -17.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8847  -18.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5993  -17.7906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3489  -18.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9011  -17.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4887  -16.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6817  -16.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7215  -17.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7416  -16.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0268  -18.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3125  -17.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5979  -18.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8835  -17.7892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5977  -19.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1690  -18.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171  -17.8683    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8649  -18.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772  -19.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842  -19.0244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  7  1  0
  3  4  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  7  8  1  0
 14 17  1  6
 10 18  2  0
  8  9  1  0
 10 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
  7 11  1  1
 21 23  2  0
  5  6  2  0
 22 24  1  0
 24 25  1  0
 11 12  1  0
 12 13  1  0
  6  1  1  0
  1  2  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA397475

   N1-((S)-2-((S)-3-hydroxypyrrolidin-1-yl)-1-phenylethyl)-N1-methyl-N4-(thiazol-2-yl)succinamide

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: 402.52

Molecular Weight (Monoisotopic): 402.1726

AlogP: 2.13

#Rotatable Bonds: 8

Polar Surface Area: 85.77

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.77

CX Basic pKa: 8.40

CX LogP: 0.39

CX LogD: 0.14

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -1.49

References

1. Chu GH, Gu M, Cassel JA, Belanger S, Graczyk TM, DeHaven RN, Conway-James N, Koblish M, Little PJ, DeHaven-Hudkins DL, Dolle RE..  (2007)  Novel malonamide derivatives as potent kappa opioid receptor agonists.,  17  (7): [PMID:17307360] [10.1016/j.bmcl.2007.01.053]

Source

Source(1):

• Scientific Literature