Sodium(1R,4S,5R)-1,4,5-Trihydroxy-3-(5-methylbenzo[b]-thiophen-2-yl)methoxycyclohexan-1-carboxylate

ID: ALA567564

PubChem CID: 44627427

Max Phase: Preclinical

Molecular Formula: C17H17NaO6S

Molecular Weight: 350.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2sc(COC3=C[C@@](O)(C(=O)[O-])C[C@@H](O)[C@@H]3O)cc2c1.[Na+]

Standard InChI:  InChI=1S/C17H18O6S.Na/c1-9-2-3-14-10(4-9)5-11(24-14)8-23-13-7-17(22,16(20)21)6-12(18)15(13)19;/h2-5,7,12,15,18-19,22H,6,8H2,1H3,(H,20,21);/q;+1/p-1/t12-,15+,17-;/m1./s1

Standard InChI Key:  QDNKFBLMZXFZAX-NQLNPJAESA-M

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    4.2397   -2.7806    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   11.2016   -4.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2016   -5.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9141   -5.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6264   -5.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6264   -4.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9141   -4.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4934   -3.6269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3189   -3.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1443   -3.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8993   -2.9160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9141   -6.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4874   -6.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3406   -6.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7719   -5.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0577   -6.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3025   -5.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9719   -6.8214    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1648   -6.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7562   -6.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9362   -6.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5240   -6.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9377   -7.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7562   -7.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6985   -6.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 13  1  0
  5  6  1  0
  5 14  1  1
  6  7  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
  7  8  1  6
 17 20  1  0
 19 18  1  0
 18 16  1  0
  7  9  1  0
  2  3  2  0
 19 20  2  0
  9 10  1  0
 20 21  1  0
  2  7  1  0
 21 22  2  0
  9 11  2  0
 22 23  1  0
  3  4  1  0
 23 24  2  0
 24 19  1  0
  4 12  1  6
 22 25  1  0
  4  5  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: 350.39

Molecular Weight (Monoisotopic): 350.0824

AlogP: 1.55

#Rotatable Bonds: 4

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.99

CX Basic pKa: ┄

CX LogP: 1.09

CX LogD: -2.07

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 0.16

References

1. Prazeres VF, Tizón L, Otero JM, Guardado-Calvo P, Llamas-Saiz AL, van Raaij MJ, Castedo L, Lamb H, Hawkins AR, González-Bello C..  (2010)  Synthesis and biological evaluation of new nanomolar competitive inhibitors of Helicobacter pylori type II dehydroquinase. Structural details of the role of the aromatic moieties with essential residues.,  53  (1): [PMID:19911771] [10.1021/jm9010466]

2. 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