sodium(1R,4S,5R)-3-((6-chlorobenzo[b]thiophen-2-yl)methoxy)-1,4,5-trihydroxycyclohex-2-enecarboxylate

ID: ALA1823560

PubChem CID: 53473575

Max Phase: Preclinical

Molecular Formula: C16H14ClNaO6S

Molecular Weight: 370.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])[C@]1(O)C=C(OCc2cc3ccc(Cl)cc3s2)[C@@H](O)[C@H](O)C1.[Na+]

Standard InChI:  InChI=1S/C16H15ClO6S.Na/c17-9-2-1-8-3-10(24-13(8)4-9)7-23-12-6-16(22,15(20)21)5-11(18)14(12)19;/h1-4,6,11,14,18-19,22H,5,7H2,(H,20,21);/q;+1/p-1/t11-,14+,16-;/m1./s1

Standard InChI Key:  WIHAZPADHQBQSS-YMOADCPFSA-M

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    2.8438   -3.0938    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    0.4130   -3.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8302   -3.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2430   -3.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1209   -4.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1209   -5.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8339   -5.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -5.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -4.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690   -3.0904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278   -2.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614   -5.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8339   -6.2908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937   -5.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097   -5.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244   -5.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801   -5.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -6.2921    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9179   -6.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3267   -5.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1473   -5.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5598   -6.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1458   -7.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3267   -7.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5574   -7.8915    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  7 13  1  6
  5  3  1  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 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
 23 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: 370.81

Molecular Weight (Monoisotopic): 370.0278

AlogP: 1.90

#Rotatable Bonds: 4

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: 3.92

CX Basic pKa: ┄

CX LogP: 1.18

CX LogD: -2.02

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: 0.10

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