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

ID: ALA1823565

PubChem CID: 53473830

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(OCc2ccc3sccc3c2)=C1Cc1ccc2sccc2c1.[Na+]

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

Standard InChI Key:  ZUWXZTJDMFMDRG-DCTXAINWSA-M

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   16.2187  -23.5625    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   14.1838  -24.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6013  -24.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0143  -24.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8917  -25.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8917  -26.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6050  -26.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3182  -26.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3182  -25.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8408  -24.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5990  -23.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0334  -26.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6050  -27.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1765  -26.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4601  -26.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7450  -26.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1742  -24.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1709  -24.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0312  -26.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0387  -27.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7504  -27.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8855  -23.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4480  -22.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4545  -23.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3173  -27.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3120  -26.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5259  -26.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0452  -27.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5343  -27.7225    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1645  -22.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8799  -22.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4893  -22.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1505  -21.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3318  -21.6996    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  9  3  1  0
 17 18  1  0
  3  2  1  0
 16 19  2  0
 19 26  1  0
  4 10  1  0
 25 20  1  0
  3  4  1  1
 20 21  2  0
 21 16  1  0
  4 11  2  0
 18 22  2  0
 22 31  1  0
  5  6  2  0
 30 23  1  0
  8 12  1  1
 23 24  2  0
 24 18  1  0
 25 26  2  0
  7 13  1  6
  5  3  1  0
  6 14  1  0
  6  7  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 25  1  0
 30 31  2  0
 14 15  1  0
  7  8  1  0
 15 16  1  0
  8  9  1  0
  5 17  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 30  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: 4.28

CX Basic pKa: ┄

CX LogP: 3.14

CX LogD: 0.16

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 0.34

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