3-methyl-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-9-ol

ID: ALA403333

PubChem CID: 16759910

Max Phase: Preclinical

Molecular Formula: C16H12N2O3S

Molecular Weight: 312.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2ccc3c(c2n1)NS(=O)(=O)c1ccc(O)cc1-3

Standard InChI:  InChI=1S/C16H12N2O3S/c1-9-2-3-10-4-6-12-13-8-11(19)5-7-14(13)22(20,21)18-16(12)15(10)17-9/h2-8,18-19H,1H3

Standard InChI Key:  YXCQOKDIVHUISG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    3.8426   -4.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8426   -5.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5548   -6.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5548   -4.5280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717   -4.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2682   -5.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9786   -6.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6971   -5.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9856   -4.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6981   -4.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7117   -3.2998    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9893   -3.7061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4241   -3.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1140   -2.5860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2916   -2.5860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1259   -4.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8470   -4.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8520   -3.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1397   -3.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293   -4.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -4.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5560   -4.9773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  9 12  1  0
 13 11  1  0
 11 12  1  0
  1  2  1  0
  1  4  2  0
 11 14  2  0
  2  3  2  0
 11 15  2  0
 13 21  2  0
  5  9  2  0
 21 16  1  0
  6  7  2  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
  8 10  2  0
 18 19  2  0
 19 13  1  0
  9 10  1  0
  1 20  1  0
  3  6  1  0
 10 21  1  0
  5  4  1  0
 17 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA403333

   3-methyl-6,6-dioxo-5H-quinolino[8,7-c][1,2]benzothiazin-9-ol

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: 312.35

Molecular Weight (Monoisotopic): 312.0569

AlogP: 3.03

#Rotatable Bonds: ┄

Polar Surface Area: 79.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.69

CX Basic pKa: 4.06

CX LogP: 2.12

CX LogD: 1.51

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.67

Np Likeness Score: -0.46

References

1. Xie Y, Deng S, Thomas CJ, Liu Y, Zhang YQ, Rinderspacher A, Huang W, Gong G, Wyler M, Cayanis E, Aulner N, Többen U, Chung C, Pampou S, Southall N, Vidović D, Schürer S, Branden L, Davis RE, Staudt LM, Inglese J, Austin CP, Landry DW, Smith DH, Auld DS..  (2008)  Identification of N-(quinolin-8-yl)benzenesulfonamides as agents capable of down-regulating NFkappaB activity within two separate high-throughput screens of NFkappaB activation.,  18  (1): [PMID:18024113] [10.1016/j.bmcl.2007.10.100]

2. Tsai KC, Teng LW, Shao YM, Chen YC, Lee YC, Li M, Hsiao NW..  (2009)  The first pharmacophore model for potent NF-kappaB inhibitors.,  19  (19): [PMID:19726185] [10.1016/j.bmcl.2009.08.021]

Source

Source(1):

• Scientific Literature