2-hydrazinylpyrimidine-4-carboxylic acid

ID: ALA3793278

PubChem CID: 83672127

Max Phase: Preclinical

Molecular Formula: C5H6N4O2

Molecular Weight: 154.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NNc1nccc(C(=O)O)n1

Standard InChI:  InChI=1S/C5H6N4O2/c6-9-5-7-2-1-3(8-5)4(10)11/h1-2H,6H2,(H,10,11)(H,7,8,9)

Standard InChI Key:  AVMDBCMWSSIKTF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 11 11  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    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
    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
    2.5972    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    2.7031    0.0000 N   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
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    0.8962    0.0000 O   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
  2  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
  9 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3793278

   2-Hydrazinylpyrimidine-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: 154.13

Molecular Weight (Monoisotopic): 154.0491

AlogP: -0.54

#Rotatable Bonds: 2

Polar Surface Area: 101.13

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.97

CX Basic pKa: 10.39

CX LogP: -2.00

CX LogD: -2.00

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.39

Np Likeness Score: -1.08

References

1. Wu X, Fang Z, Yang B, Zhong L, Yang Q, Zhang C, Huang S, Xiang R, Suzuki T, Li LL, Yang SY..  (2016)  Discovery of KDM5A inhibitors: Homology modeling, virtual screening and structure-activity relationship analysis.,  26  (9): [PMID:27020306] [10.1016/j.bmcl.2016.03.048]

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. Bavetsias, Vassilios and 42 more authors.  2016-02-25  8-Substituted Pyrido[3,4-d]pyrimidin-4(3H)-one Derivatives As Potent, Cell Permeable, KDM4 (JMJD2) and KDM5 (JARID1) Histone Lysine Demethylase Inhibitors.  [PMID:26741168]

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. Giordano, Assunta and 5 more authors.  2018-06-20  Virtual Fragment Screening Identification of a Quinoline-5,8-dicarboxylic Acid Derivative as a Selective JMJD3 Inhibitor.  [PMID:29633584]

8. Jaikhan, Pattaporn P and 5 more authors.  2019-05-15  Identification of ortho-hydroxy anilide as a novel scaffold for lysine demethylase 5 inhibitors.  [PMID:30928196]

Source

Source(1):

• Scientific Literature