8-Hydroxy-2-[2-(3-hydroxy-4-methoxy-phenyl)-vinyl]-quinoline-7-carboxylic acid

ID: ALA37139

PubChem CID: 6475560

Max Phase: Preclinical

Molecular Formula: C19H15NO5

Molecular Weight: 337.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/c2ccc3ccc(C(=O)O)c(O)c3n2)cc1O

Standard InChI:  InChI=1S/C19H15NO5/c1-25-16-9-3-11(10-15(16)21)2-6-13-7-4-12-5-8-14(19(23)24)18(22)17(12)20-13/h2-10,21-22H,1H3,(H,23,24)/b6-2+

Standard InChI Key:  FSLDLBJGAMZARH-QHHAFSJGSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    0.8672  -10.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5810  -10.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2919  -10.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861   -9.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5634   -9.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8556   -9.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1473   -8.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484   -9.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4336   -9.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4354   -7.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -8.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193   -9.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -9.6425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -9.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937   -8.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096   -7.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5729   -9.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646   -9.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5713   -9.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653  -10.4728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4317  -10.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1400   -9.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -9.2026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093  -10.8548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7208  -10.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  3  4  2  0
 14 15  1  0
  7  8  2  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
  8  9  1  0
  9 12  2  0
  4  5  1  0
 18 19  1  0
 18 20  2  0
  8 18  1  0
 11 10  2  0
  9 21  1  0
 10  7  1  0
 17 22  2  0
 22  6  1  0
  2  3  1  0
  4 23  1  0
  5  6  2  0
  3 24  1  0
 11 12  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA37139

   8-Hydroxy-2-(3-hydroxy-4-methoxystyryl)quinoline-7-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: 337.33

Molecular Weight (Monoisotopic): 337.0950

AlogP: 3.52

#Rotatable Bonds: 4

Polar Surface Area: 99.88

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.41

CX Basic pKa: 2.35

CX LogP: 3.99

CX LogD: 0.83

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: 0.15

References

1. Zouhiri F, Mouscadet JF, Mekouar K, Desmaële D, Savouré D, Leh H, Subra F, Le Bret M, Auclair C, d'Angelo J..  (2000)  Structure-activity relationships and binding mode of styrylquinolines as potent inhibitors of HIV-1 integrase and replication of HIV-1 in cell culture.,  43  (8): [PMID:10780910] [10.1021/jm990467o]

2. Polanski J, Zouhiri F, Jeanson L, Desmaële D, d'Angelo J, Mouscadet JF, Gieleciak R, Gasteiger J, Le Bret M..  (2002)  Use of the Kohonen neural network for rapid screening of ex vivo anti-HIV activity of styrylquinolines.,  45  (21): [PMID:12361391] [10.1021/jm020845g]

3. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

4. Sliman F, Blairvacq M, Durieu E, Meijer L, Rodrigo J, Desmaële D..  (2010)  Identification and structure-activity relationship of 8-hydroxy-quinoline-7-carboxylic acid derivatives as inhibitors of Pim-1 kinase.,  20  (9): [PMID:20363627] [10.1016/j.bmcl.2010.03.061]

5. Leonard JT, Roy K..  (2008)  Exploring molecular shape analysis of styrylquinoline derivatives as HIV-1 integrase inhibitors.,  43  (1): [PMID:17452064] [10.1016/j.ejmech.2007.02.021]

Source

Source(1):

• Scientific Literature