8,8'-Disulfanediylbis(quinoline-3-carboxylic Acid)

ID: ALA4093484

Cas Number: 1414882-25-9

PubChem CID: 70790019

Max Phase: Preclinical

Molecular Formula: C20H12N2O4S2

Molecular Weight: 408.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2c(SSc3cccc4cc(C(=O)O)cnc34)cccc2c1

Standard InChI:  InChI=1S/C20H12N2O4S2/c23-19(24)13-7-11-3-1-5-15(17(11)21-9-13)27-28-16-6-2-4-12-8-14(20(25)26)10-22-18(12)16/h1-10H,(H,23,24)(H,25,26)

Standard InChI Key:  RCYABFBTLSDRIP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.5777  -21.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5765  -22.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2846  -22.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2828  -21.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9914  -21.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9921  -22.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7007  -22.7831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4089  -22.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4042  -21.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6951  -21.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2865  -23.6063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.1094  -21.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8196  -21.5415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1044  -20.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5797  -24.0165    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5816  -24.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5822  -26.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2913  -26.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2862  -25.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8730  -26.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8721  -25.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1689  -24.8396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4660  -25.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4709  -26.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1747  -26.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7657  -26.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0555  -26.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7708  -27.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  1  0
 16 21  2  0
 20 17  2  0
 17 18  1  0
 18 19  2  0
 19 16  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093484

   8-[(3-Carboxy-8-quinolyl)disulfanyl]quinoline-3-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: 408.46

Molecular Weight (Monoisotopic): 408.0238

AlogP: 4.98

#Rotatable Bonds: 5

Polar Surface Area: 100.38

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.45

CX Basic pKa: 1.83

CX LogP: 4.20

CX LogD: -2.39

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -0.40

References

1. Perez C, Li J, Parlati F, Rouffet M, Ma Y, Mackinnon AL, Chou TF, Deshaies RJ, Cohen SM..  (2017)  Discovery of an Inhibitor of the Proteasome Subunit Rpn11.,  60  (4): [PMID:28191850] [10.1021/acs.jmedchem.6b01379]

Source

Source(1):

• Scientific Literature