N1-((S)-2-((S)-3-hydroxypyrrolidin-1-yl)-1-phenylethyl)-N1-methyl-N3-(pyridin-3-yl)malonamide

ID: ALA425836

PubChem CID: 11440457

Max Phase: Preclinical

Molecular Formula: C21H26N4O3

Molecular Weight: 382.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C(=O)CC(=O)Nc1cccnc1)[C@H](CN1CC[C@H](O)C1)c1ccccc1

Standard InChI:  InChI=1S/C21H26N4O3/c1-24(21(28)12-20(27)23-17-8-5-10-22-13-17)19(16-6-3-2-4-7-16)15-25-11-9-18(26)14-25/h2-8,10,13,18-19,26H,9,11-12,14-15H2,1H3,(H,23,27)/t18-,19+/m0/s1

Standard InChI Key:  QRMWODNOOLVFGC-RBUKOAKNSA-N

Molfile:  

     RDKit          2D

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    0.5932  -23.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081  -23.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245  -23.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0216  -22.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063  -21.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079  -24.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5933  -24.8234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931  -25.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1211  -24.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222  -24.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368  -24.4114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4864  -24.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386  -24.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6262  -23.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8192  -23.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8590  -24.2201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209  -23.5857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8357  -24.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500  -24.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498  -23.5853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2646  -24.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9790  -24.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800  -23.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6935  -23.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4090  -23.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4066  -24.4146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6925  -24.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  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  2  0
  2  3  1  0
 20 22  1  0
  7 11  1  1
 22 23  1  0
  5  6  2  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
 12 13  1  0
 25 26  2  0
  6  1  1  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA425836

   N1-((S)-2-((S)-3-hydroxypyrrolidin-1-yl)-1-phenylethyl)-N1-methyl-N3-(pyridin-3-yl)malonamide

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: 382.46

Molecular Weight (Monoisotopic): 382.2005

AlogP: 1.68

#Rotatable Bonds: 7

Polar Surface Area: 85.77

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.12

CX Basic pKa: 8.23

CX LogP: 0.59

CX LogD: -0.30

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -1.19

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