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

ID: ALA1823568

PubChem CID: 46241000

Max Phase: Preclinical

Molecular Formula: C19H19NaO6S

Molecular Weight: 376.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCC1=C(OCc2cc3ccccc3s2)[C@@H](O)[C@H](O)C[C@]1(O)C(=O)[O-].[Na+]

Standard InChI:  InChI=1S/C19H20O6S.Na/c1-2-5-13-17(16(21)14(20)9-19(13,24)18(22)23)25-10-12-8-11-6-3-4-7-15(11)26-12;/h2-4,6-8,14,16,20-21,24H,1,5,9-10H2,(H,22,23);/q;+1/p-1/t14-,16+,19-;/m1./s1

Standard InChI Key:  LNMHBYSSVCBMFO-BSLPGFAVSA-M

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    1.7500   -5.6563    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -0.3042   -6.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125   -7.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5248   -6.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -7.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -8.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -8.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -8.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -7.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -6.3075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -5.5968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421   -8.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -9.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097   -8.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0248   -8.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386   -8.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934   -8.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8244   -9.5054    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120   -7.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3153   -6.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261   -9.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0395   -8.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8623   -8.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2727   -9.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8544  -10.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0329  -10.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315   -5.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 14  1  0
  6  7  1  0
 14 15  1  0
  7  8  1  0
 15 16  1  0
 16 17  2  0
  8  9  1  0
  9  3  1  0
 17 22  1  0
 21 18  1  0
 18 16  1  0
  3  2  1  0
  5 19  1  0
  4 10  1  0
 19 20  1  0
  3  4  1  1
  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 25  1  0
  7 13  1  6
 25 26  2  0
 26 21  1  0
  5  3  1  0
 20 27  2  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: 376.43

Molecular Weight (Monoisotopic): 376.0981

AlogP: 2.19

#Rotatable Bonds: 6

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.13

CX Basic pKa: ┄

CX LogP: 1.41

CX LogD: -1.67

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: 0.59

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