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

ID: ALA1823570

PubChem CID: 53473834

Max Phase: Preclinical

Molecular Formula: C22H21NaO6S2

Molecular Weight: 446.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2sc(CC3=C(OCc4cccs4)[C@@H](O)[C@H](O)C[C@]3(O)C(=O)[O-])cc2c1.[Na+]

Standard InChI:  InChI=1S/C22H22O6S2.Na/c1-12-4-5-18-13(7-12)8-15(30-18)9-16-20(28-11-14-3-2-6-29-14)19(24)17(23)10-22(16,27)21(25)26;/h2-8,17,19,23-24,27H,9-11H2,1H3,(H,25,26);/q;+1/p-1/t17-,19+,22-;/m1./s1

Standard InChI Key:  ZMWORTFUKCQSJP-FVJIEKSSSA-M

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.6250  -13.9063    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -1.5125  -14.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958  -15.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835  -14.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042  -15.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042  -16.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0921  -17.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3801  -16.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3801  -15.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1415  -14.7033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982  -13.9926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337  -17.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0921  -17.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180  -17.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331  -16.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9470  -17.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7018  -16.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327  -17.9013    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8394  -18.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2478  -17.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203  -15.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237  -14.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576  -14.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924  -14.1205    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9423  -13.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1199  -13.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123  -12.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261  -11.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9516  -11.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555  -12.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7176  -11.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  5  3  1  0
 26 27  1  0
  6 14  1  0
 27 28  2  0
  6  7  1  0
 28 29  1  0
 14 15  1  0
 29 30  2  0
 30 25  1  0
  7  8  1  0
 28 31  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: 446.55

Molecular Weight (Monoisotopic): 446.0858

AlogP: 3.23

#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: 4.08

CX Basic pKa: ┄

CX LogP: 2.83

CX LogD: -0.28

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -0.21

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