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

ID: ALA1823563

PubChem CID: 46240998

Max Phase: Preclinical

Molecular Formula: C27H25NaO6S2

Molecular Weight: 510.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2sc(COC3=C(Cc4cc5cc(C)ccc5s4)[C@@](O)(C(=O)[O-])C[C@@H](O)[C@@H]3O)cc2c1.[Na+]

Standard InChI:  InChI=1S/C27H26O6S2.Na/c1-14-3-5-22-16(7-14)9-18(34-22)11-20-25(24(29)21(28)12-27(20,32)26(30)31)33-13-19-10-17-8-15(2)4-6-23(17)35-19;/h3-10,21,24,28-29,32H,11-13H2,1-2H3,(H,30,31);/q;+1/p-1/t21-,24+,27-;/m1./s1

Standard InChI Key:  DANBJVULHWQWEO-SCDOXDKZSA-M

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   16.0000  -15.4375    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   14.0444  -16.2342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4614  -16.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8743  -16.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7523  -17.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7523  -18.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4651  -18.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1779  -18.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1779  -17.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7001  -16.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4591  -15.5177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8926  -18.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4651  -19.4293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0377  -18.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3219  -18.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6072  -18.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8516  -18.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5214  -19.4306    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7139  -19.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3050  -18.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4845  -18.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0720  -19.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4859  -20.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3050  -20.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0355  -16.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0321  -16.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6988  -15.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3626  -15.6457    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.6145  -14.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4363  -14.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8455  -14.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4341  -13.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6091  -13.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2036  -14.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2461  -19.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8450  -12.7212    0.0000 C   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
 22 35  1  0
 17 20  1  0
 32 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: 510.63

Molecular Weight (Monoisotopic): 510.1171

AlogP: 4.69

#Rotatable Bonds: 6

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.13

CX Basic pKa: ┄

CX LogP: 4.43

CX LogD: 1.36

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.30

Np Likeness Score: 0.26

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