Sodium(1R,4S,5R)-3-(Benzo[b]thiophen-2-yl)methoxy-1,4,5-trihydroxy-2-(thien-2-yl)methylcyclohex-2-en-1-carboxylate

ID: ALA1823569

PubChem CID: 53473833

Max Phase: Preclinical

Molecular Formula: C21H19NaO6S2

Molecular Weight: 432.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])[C@@]1(O)C[C@@H](O)[C@H](O)C(OCc2cc3ccccc3s2)=C1Cc1cccs1.[Na+]

Standard InChI:  InChI=1S/C21H20O6S2.Na/c22-16-10-21(26,20(24)25)15(9-13-5-3-7-28-13)19(18(16)23)27-11-14-8-12-4-1-2-6-17(12)29-14;/h1-8,16,18,22-23,26H,9-11H2,(H,24,25);/q;+1/p-1/t16-,18+,21-;/m1./s1

Standard InChI Key:  CAEAXSWCSFHRKG-ZZBFITHQSA-M

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   17.0000   -4.2500    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   14.9059   -5.0423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3225   -5.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7350   -5.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6142   -6.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6142   -7.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3262   -7.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0383   -7.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0383   -6.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5600   -5.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3202   -4.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7523   -7.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3262   -8.2342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9002   -7.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1851   -7.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4711   -7.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7162   -7.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3854   -8.2355    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.8980   -5.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8946   -4.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5607   -4.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2258   -4.4543    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.4774   -3.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2984   -3.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5835   -8.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1702   -7.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3473   -7.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9367   -8.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3552   -9.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1767   -9.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 15 16  1  0
 16 17  2  0
  8  9  1  0
  9  3  1  0
 17 26  1  0
 25 18  1  0
 18 16  1  0
  3  2  1  0
  5 19  1  0
  4 10  1  0
 19 20  1  0
 20 21  2  0
  3  4  1  1
  4 11  2  0
 21 24  1  0
 23 22  1  0
 22 20  1  0
  5  6  2  0
  8 12  1  1
 23 24  2  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
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: 432.52

Molecular Weight (Monoisotopic): 432.0701

AlogP: 2.92

#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: 4.00

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: -0.85

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -0.09

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