(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-enecarboxylic acid

ID: ALA1823559

PubChem CID: 56662152

Max Phase: Preclinical

Molecular Formula: C15H15N3O5

Molecular Weight: 317.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cn(-c3ccccc3)nn2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C15H15N3O5/c19-12-7-15(23,14(21)22)6-10(13(12)20)11-8-18(17-16-11)9-4-2-1-3-5-9/h1-6,8,12-13,19-20,23H,7H2,(H,21,22)/t12-,13-,15+/m1/s1

Standard InChI Key:  FLIDIIDIPNIAQH-NFAWXSAZSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -1.4167  -13.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000  -14.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877  -13.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083  -14.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083  -15.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963  -15.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843  -15.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843  -14.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373  -13.6117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0023  -12.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4296  -15.9885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963  -16.8083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238  -15.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2164  -15.7598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791  -16.4428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725  -17.0940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967  -16.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015  -17.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2015  -18.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4306  -18.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8584  -19.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0540  -19.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287  -18.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  6
 13 14  1  0
  4  2  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  2  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 13  2  0
  5 13  1  0
  2  1  1  0
 16 18  1  0
  3  9  1  0
 18 19  2  0
  2  3  1  1
 19 20  1  0
  3 10  2  0
 20 21  2  0
  4  5  2  0
 21 22  1  0
  7 11  1  1
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1823559

   (1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyltriazol-4-yl)cyclohex-2-ene-1-carboxylic acid

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: 317.30

Molecular Weight (Monoisotopic): 317.1012

AlogP: -0.41

#Rotatable Bonds: 3

Polar Surface Area: 128.70

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.19

CX Basic pKa: ┄

CX LogP: 0.01

CX LogD: -3.44

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.61

Np Likeness Score: -0.18

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]

2. Tran AT, Cergol KM, Britton WJ, Imran Bokhari SA, Ibrahim M, Lapthorn AJ, Payne RJ.  (2010)  Rapid assembly of potent type II dehydroquinase inhibitors viaClick chemistry,  1  (4): [10.1039/C0MD00097C]

Source

Source(1):

• Scientific Literature