sodium(1R,4S,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylmethoxy)-2-(thiophen-2-ylmethyl)cyclohex-2-enecarboxylate

ID: ALA1823567

PubChem CID: 53473831

Max Phase: Preclinical

Molecular Formula: C17H17NaO6S2

Molecular Weight: 382.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])[C@@]1(O)C[C@@H](O)[C@H](O)C(OCc2cccs2)=C1Cc1cccs1.[Na+]

Standard InChI:  InChI=1S/C17H18O6S2.Na/c18-13-8-17(22,16(20)21)12(7-10-3-1-5-24-10)15(14(13)19)23-9-11-4-2-6-25-11;/h1-6,13-14,18-19,22H,7-9H2,(H,20,21);/q;+1/p-1/t13-,14+,17-;/m1./s1

Standard InChI Key:  CFGWETSGSZVRKQ-SLINCCQESA-M

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   16.6250    2.7812    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   14.5208    1.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9375    1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3498    1.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2292    0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2292    0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9412   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6532    0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6532    0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1748    1.9675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9352    2.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3671   -0.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9412   -1.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5153   -0.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8002    0.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0864   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3316   -0.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0006   -1.2304    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1940   -1.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7855   -0.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5130    1.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5097    2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1757    2.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8409    2.5503    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.0925    3.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9135    3.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  6 14  1  0
  6  7  1  0
 14 15  1  0
  7  8  1  0
 15 16  1  0
 16 17  2  0
  8  9  1  0
  9  3  1  0
 17 20  1  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
  5 21  1  0
  4 11  2  0
 21 22  1  0
 22 23  2  0
  5  6  2  0
  8 12  1  1
 23 26  1  0
 25 24  1  0
 24 22  1  0
  7 13  1  6
 25 26  2  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: 382.46

Molecular Weight (Monoisotopic): 382.0545

AlogP: 1.76

#Rotatable Bonds: 6

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.96

CX Basic pKa: ┄

CX LogP: 1.22

CX LogD: -1.97

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: 0.28

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