sodium(1R,4S,5R)-3-((6-chlorobenzo[b]thiophen-2-yl)methoxy)-2-((6-chlorobenzo[b]thiophen-2-yl)methyl)-1,4,5-trihydroxycyclohex-2-enecarboxylate

ID: ALA1823564

PubChem CID: 53473756

Max Phase: Preclinical

Molecular Formula: C25H19Cl2NaO6S2

Molecular Weight: 551.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])[C@@]1(O)C[C@@H](O)[C@H](O)C(OCc2cc3ccc(Cl)cc3s2)=C1Cc1cc2ccc(Cl)cc2s1.[Na+]

Standard InChI:  InChI=1S/C25H20Cl2O6S2.Na/c26-14-3-1-12-5-16(34-20(12)7-14)9-18-23(22(29)19(28)10-25(18,32)24(30)31)33-11-17-6-13-2-4-15(27)8-21(13)35-17;/h1-8,19,22,28-29,32H,9-11H2,(H,30,31);/q;+1/p-1/t19-,22+,25-;/m1./s1

Standard InChI Key:  SSKYEXDDYLAVPW-DCTXAINWSA-M

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    2.8438  -23.8750    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    0.5722  -24.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899  -25.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4032  -24.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799  -25.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799  -26.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936  -26.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074  -26.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074  -25.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2302  -24.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876  -23.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230  -27.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936  -27.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4358  -27.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1526  -26.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8682  -27.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6248  -26.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542  -27.8233    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7627  -27.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722  -27.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9938  -27.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4069  -27.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9923  -28.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1721  -28.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381  -25.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4414  -24.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263  -24.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118  -24.0334    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596  -23.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366  -23.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732  -22.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0389  -21.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8649  -21.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2710  -22.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4045  -29.4249    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2820  -21.1120    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 16  1  0
  3  2  1  0
  4 10  1  0
 19 20  2  0
  3  4  1  1
 20 21  1  0
  4 11  2  0
 21 22  2  0
  5  6  2  0
 22 23  1  0
  8 12  1  1
 23 24  2  0
 24 19  1  0
  5 25  1  0
  7 13  1  6
 25 26  1  0
 26 27  2  0
  5  3  1  0
  6 14  1  0
 27 30  1  0
 29 28  1  0
 28 26  1  0
  6  7  1  0
 14 15  1  0
 29 30  2  0
  7  8  1  0
 30 31  1  0
 15 16  1  0
 31 32  2  0
 16 17  2  0
 32 33  1  0
  8  9  1  0
 33 34  2  0
 34 29  1  0
  9  3  1  0
 23 35  1  0
 17 20  1  0
 33 36  1  0
M  CHG  2   1   1  10  -1
M  END

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: 551.47

Molecular Weight (Monoisotopic): 550.0078

AlogP: 5.38

#Rotatable Bonds: 6

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.18

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 1.57

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.26

Np Likeness Score: 0.22

References

1. Tizón L, Otero JM, Prazeres VF, Llamas-Saiz AL, Fox GC, van Raaij MJ, Lamb H, Hawkins AR, Ainsa JA, Castedo L, González-Bello C..  (2011)  A prodrug approach for improving antituberculosis activity of potent Mycobacterium tuberculosis type II dehydroquinase inhibitors.,  54  (17): [PMID:21780742] [10.1021/jm2006063]

Source

Source(1):

• Scientific Literature