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

ID: ALA1823571

PubChem CID: 53473836

Max Phase: Preclinical

Molecular Formula: C21H19NaO6S2

Molecular Weight: 432.52

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C([O-])[C@@]1(O)C[C@@H](O)[C@H](O)C(OCc2cccs2)=C1Cc1ccc2sccc2c1.[Na+]

Standard InChI:  InChI=1S/C21H20O6S2.Na/c22-16-10-21(26,20(24)25)15(9-12-3-4-17-13(8-12)5-7-29-17)19(18(16)23)27-11-14-2-1-6-28-14;/h1-8,16,18,22-23,26H,9-11H2,(H,24,25);/q;+1/p-1/t16-,18+,21-;/m1./s1

Standard InChI Key:  KLLDWTLXBYYGKU-ZZBFITHQSA-M

Molfile:  

     RDKit          2D

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   16.5625  -12.7500    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   14.3059  -13.3933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7225  -14.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1350  -13.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0141  -14.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0141  -15.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7262  -15.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4383  -15.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4383  -14.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9600  -13.3883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7202  -12.6774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1523  -15.7653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7262  -16.5852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3002  -15.7653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5851  -15.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8711  -15.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1162  -15.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7854  -16.5865    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9786  -16.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5701  -16.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2980  -14.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2946  -13.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0079  -12.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5730  -12.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5795  -12.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2881  -11.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0023  -12.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6108  -11.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2726  -10.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4552  -10.8411    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  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
  5 21  1  0
  4 11  2  0
 21 22  1  0
  5  6  2  0
 22 23  2  0
 23 27  1  0
  8 12  1  1
 26 24  1  0
 24 25  2  0
 25 22  1  0
 26 27  2  0
  7 13  1  6
  5  3  1  0
  6 14  1  0
  6  7  1  0
 14 15  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 26  1  0
M  CHG  2   1   1  10  -1
M  END

Associated Targets(non-human)

aroQ 3-dehydroquinate dehydratase (62 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
aroQ 3-dehydroquinate dehydratase (50 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 432.52Molecular Weight (Monoisotopic): 432.0701AlogP: 2.92#Rotatable Bonds: 6
Polar Surface Area: 107.22Molecular Species: ACIDHBA: 7HBD: 4
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 4.15CX Basic pKa: CX LogP: 2.18CX LogD: -0.89
Aromatic Rings: 3Heavy Atoms: 29QED Weighted: 0.48Np Likeness Score: -0.07

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