6-((2-oxo-2-(piperidin-1-yl)ethylamino)methyl)pyridazine-4-carboxylic acid

ID: ALA3786275

PubChem CID: 118420691

Max Phase: Preclinical

Molecular Formula: C13H18N4O3

Molecular Weight: 278.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnnc(CNCC(=O)N2CCCCC2)c1

Standard InChI:  InChI=1S/C13H18N4O3/c18-12(17-4-2-1-3-5-17)9-14-8-11-6-10(13(19)20)7-15-16-11/h6-7,14H,1-5,8-9H2,(H,19,20)

Standard InChI Key:  ROLOXANLBFDXOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    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 N   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
   -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
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4969   -0.4591    0.0000 O   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
   -9.0994    0.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3984    1.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3985    2.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0995    3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    2.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
  7 12  2  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3786275

   6-[[(2-Oxo-2-piperidin-1-ylethyl)amino]methyl]pyridazine-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: 278.31

Molecular Weight (Monoisotopic): 278.1379

AlogP: 0.28

#Rotatable Bonds: 5

Polar Surface Area: 95.42

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.50

CX Basic pKa: 6.91

CX LogP: -3.38

CX LogD: -3.88

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.80

Np Likeness Score: -1.40

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