ethyl 4-hydroxy-2-methylquinoline-3-carboxylate

ID: ALA214415

Cas Number: 7521-63-3

PubChem CID: 2986317

Max Phase: Preclinical

Molecular Formula: C13H13NO3

Molecular Weight: 231.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1c(C)nc2ccccc2c1O

Standard InChI:  InChI=1S/C13H13NO3/c1-3-17-13(16)11-8(2)14-10-7-5-4-6-9(10)12(11)15/h4-7H,3H2,1-2H3,(H,14,15)

Standard InChI Key:  PHRRSYMXOIKRAW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -5.7602    2.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7613    1.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0465    0.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0483    2.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3328    2.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3321    1.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    0.7701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9016    1.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    2.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6224    2.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6268    3.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1945    2.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4774    2.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    3.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654    2.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484    2.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856    0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  8  9  1  0
  4  1  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
  2  3  1  0
  9 12  1  0
  5  6  1  0
 12 13  1  0
  3  6  2  0
 12 14  2  0
  6  7  1  0
 13 15  1  0
  1  2  2  0
 15 16  1  0
  7  8  2  0
  8 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA214415

   3-Quinolinecarboxylic acid, 4-hydroxy-2-methyl-, ethyl ester

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: 231.25

Molecular Weight (Monoisotopic): 231.0895

AlogP: 2.43

#Rotatable Bonds: 2

Polar Surface Area: 59.42

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.65

CX Basic pKa: 2.24

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.81

Np Likeness Score: -0.59

References

1. Mai A, Rotili D, Tarantino D, Ornaghi P, Tosi F, Vicidomini C, Sbardella G, Nebbioso A, Miceli M, Altucci L, Filetici P..  (2006)  Small-molecule inhibitors of histone acetyltransferase activity: identification and biological properties.,  49  (23): [PMID:17154519] [10.1021/jm060601m]

2. Mai A, Rotili D, Tarantino D, Nebbioso A, Castellano S, Sbardella G, Tini M, Altucci L..  (2009)  Identification of 4-hydroxyquinolines inhibitors of p300/CBP histone acetyltransferases.,  19  (4): [PMID:19144517] [10.1016/j.bmcl.2008.12.097]

3. Bouchut A, Rotili D, Pierrot C, Valente S, Lafitte S, Schultz J, Hoglund U, Mazzone R, Lucidi A, Fabrizi G, Pechalrieu D, Arimondo PB, Skinner-Adams TS, Chua MJ, Andrews KT, Mai A, Khalife J..  (2019)  Identification of novel quinazoline derivatives as potent antiplasmodial agents.,  161  [PMID:30366254] [10.1016/j.ejmech.2018.10.041]

4. Huang M, Huang J, Zheng Y, Sun Q..  (2019)  Histone acetyltransferase inhibitors: An overview in synthesis, structure-activity relationship and molecular mechanism.,  178  [PMID:31195169] [10.1016/j.ejmech.2019.05.078]

Source

Source(1):

• Scientific Literature