2-(((1-cinnamyl-1H-imidazol-2-yl)methylamino)methyl)isonicotinic acid

ID: ALA3786239

PubChem CID: 118421047

Max Phase: Preclinical

Molecular Formula: C20H20N4O2

Molecular Weight: 348.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccnc(CNCc2nccn2C/C=C/c2ccccc2)c1

Standard InChI:  InChI=1S/C20H20N4O2/c25-20(26)17-8-9-22-18(13-17)14-21-15-19-23-10-12-24(19)11-4-7-16-5-2-1-3-6-16/h1-10,12-13,21H,11,14-15H2,(H,25,26)/b7-4+

Standard InChI Key:  KTXRFMCORGKUII-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

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    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 N   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
    0.0031   -3.0008    0.0000 C   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
   -3.8990    0.7455    0.0000 N   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
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351   -3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -3.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8525    1.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8524    0.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6317   -0.7404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1609    2.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5870    3.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8959    4.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3220    5.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6328    6.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0590    7.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1745    6.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8638    4.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4375    4.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 12  1  0
  7 13  2  0
 11 14  1  0
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 16 17  1  0
 17 11  2  0
 14 18  1  0
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 20 21  1  0
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 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3786239

   2-[[[1-[(E)-3-phenylprop-2-enyl]imidazol-2-yl]methylamino]methyl]pyridine-4-carboxylic acid

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: 348.41

Molecular Weight (Monoisotopic): 348.1586

AlogP: 2.98

#Rotatable Bonds: 8

Polar Surface Area: 80.04

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.39

CX Basic pKa: 6.53

CX LogP: 0.43

CX LogD: -0.32

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: -0.91

References

1. McAllister TE, England KS, Hopkinson RJ, Brennan PE, Kawamura A, Schofield CJ..  (2016)  Recent Progress in Histone Demethylase Inhibitors.,  59  (4): [PMID:26710088] [10.1021/acs.jmedchem.5b01758]

2. Rotili, Dante D and 18 more authors.  2014-01-09  Pan-histone demethylase inhibitors simultaneously targeting Jumonji C and lysine-specific demethylases display high anticancer activities.  [PMID:24325601]

3. Schiller, Rachel and 14 more authors.  2014-03  A cell-permeable ester derivative of the JmjC histone demethylase inhibitor IOX1.  [PMID:24504543]

4. England, Katherine S and 12 more authors.  2014-12-01  Optimisation of a triazolopyridine based histone demethylase inhibitor yields a potent and selective KDM2A (FBXL11) inhibitor.  [PMID:26682034]

5. Korczynska, Magdalena M and 14 more authors.  2016-02-25  Docking and Linking of Fragments To Discover Jumonji Histone Demethylase Inhibitors.  [PMID:26699912]

6. Westaway, Susan M SM and 33 more authors.  2016-02-25  Cell Penetrant Inhibitors of the KDM4 and KDM5 Families of Histone Lysine Demethylases. 1. 3-Amino-4-pyridine Carboxylate Derivatives.  [PMID:26771107]

7. Letfus, Vatroslav; Jelić, Dubravko; Bokulić, Ana; Petrinić Grba, Adriana and Koštrun, Sanja.  2020-01-01  Rational design, synthesis and biological profiling of new KDM4C inhibitors.  [PMID:31784197]

Source

Source(1):

• Scientific Literature