Sodium(1R,4S,5R)-3-(Benzo[b]thiophen-2-yl)methoxy-2-(benzo[b]thiophen-2-yl)methyl-1,4,5-trihydroxycyclohex-2-en-1-carboxylate

ID: ALA1823562

PubChem CID: 46240889

Max Phase: Preclinical

Molecular Formula: C25H21NaO6S2

Molecular Weight: 482.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])[C@@]1(O)C[C@@H](O)[C@H](O)C(OCc2cc3ccccc3s2)=C1Cc1cc2ccccc2s1.[Na+]

Standard InChI:  InChI=1S/C25H22O6S2.Na/c26-19-12-25(30,24(28)29)18(11-16-9-14-5-1-3-7-20(14)32-16)23(22(19)27)31-13-17-10-15-6-2-4-8-21(15)33-17;/h1-10,19,22,26-27,30H,11-13H2,(H,28,29);/q;+1/p-1/t19-,22+,25-;/m1./s1

Standard InChI Key:  HHEURLRNPYUJGT-DCTXAINWSA-M

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    2.2812  -15.9687    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -0.0794  -16.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383  -17.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516  -16.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717  -17.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717  -18.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420  -18.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558  -18.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558  -17.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5787  -16.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360  -15.7561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7714  -18.8512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420  -19.6730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874  -18.8512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042  -18.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198  -18.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764  -18.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6058  -19.6743    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4143  -19.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8238  -19.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6453  -19.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585  -19.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6439  -20.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8237  -20.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0897  -17.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0930  -16.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253  -15.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634  -15.8843    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112  -15.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882  -15.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784  -14.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905  -13.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5165  -13.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9226  -14.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 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
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: 482.58

Molecular Weight (Monoisotopic): 482.0858

AlogP: 4.07

#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: 4.17

CX Basic pKa: ┄

CX LogP: 3.41

CX LogD: 0.35

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 0.35

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