3-(-(2,5-dimethoxy-4-(-phenyldiazenyl)phenyl)diazenyl)quinoline-2,4-diol

ID: ALA1939686

Max Phase: Preclinical

Molecular Formula: C23H19N5O4

Molecular Weight: 429.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-78676

Canonical SMILES:  COc1cc(/N=N/c2c(O)nc3ccccc3c2O)c(OC)cc1/N=N/c1ccccc1

Standard InChI:  InChI=1S/C23H19N5O4/c1-31-19-13-18(20(32-2)12-17(19)26-25-14-8-4-3-5-9-14)27-28-21-22(29)15-10-6-7-11-16(15)24-23(21)30/h3-13H,1-2H3,(H2,24,29,30)/b26-25+,28-27+

Standard InChI Key:  DHQPPOYLOLLOCW-PAMTUDGESA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    9.9975  -14.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1737  -14.1189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7618  -13.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9379  -13.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5260  -12.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9379  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5260  -11.2636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9379  -10.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7618  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1737  -12.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9975  -12.6892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4095  -13.4041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2333  -13.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6452  -12.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4691  -12.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8810  -13.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4691  -14.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6452  -14.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6980  -12.6892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2860  -11.9785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4622  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0503  -12.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4622  -13.4041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2264  -12.6892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8145  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9906  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5787  -11.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9906  -10.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8145  -10.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2264  -11.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0503  -11.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4622  -10.5488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  2  0
  3 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 13 18  1  0
  5 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 25 30  1  0
 30 31  2  0
 21 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1939686

   ---

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: 429.44

Molecular Weight (Monoisotopic): 429.1437

AlogP: 6.49

#Rotatable Bonds: 6

Polar Surface Area: 121.25

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.16

CX Basic pKa: 0.10

CX LogP: 6.61

CX LogD: 6.55

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -0.45

References

1. Wang Y, Hess TN, Jones V, Zhou JZ, McNeil MR, Andrew McCammon J..  (2011)  Novel inhibitors of Mycobacterium tuberculosis dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD) identified by virtual screening.,  21  (23): [PMID:22014548] [10.1016/j.bmcl.2011.09.094]

Source

Source(1):

• Scientific Literature