3-(4-((3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-enyl)-1H-1,2,3-triazol-1-yl)benzoic acid

ID: ALA3221801

PubChem CID: 90668068

Max Phase: Preclinical

Molecular Formula: C16H15N3O7

Molecular Weight: 361.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(-n2cc(C3=C[C@@](O)(C(=O)O)C[C@@H](O)[C@@H]3O)nn2)c1

Standard InChI:  InChI=1S/C16H15N3O7/c20-12-6-16(26,15(24)25)5-10(13(12)21)11-7-19(18-17-11)9-3-1-2-8(4-9)14(22)23/h1-5,7,12-13,20-21,26H,6H2,(H,22,23)(H,24,25)/t12-,13-,16+/m1/s1

Standard InChI Key:  CVIDBOLEBIAPKP-IOASZLSFSA-N

Molfile:  

     RDKit          2D

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   13.3640   -6.0588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1535   -6.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9450   -6.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6422   -8.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6411   -8.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3491   -9.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0588   -8.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0559   -8.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3473   -7.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7640   -7.6243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5118   -7.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0563   -7.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6451   -6.6383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8464   -6.8113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8667   -7.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2005   -8.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0098   -8.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4913   -7.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3422   -6.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5270   -7.2142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1565   -5.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3422   -9.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7211   -8.8394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3497  -10.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6419  -10.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0573  -10.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
  8 10  1  0
 15 16  1  0
 15 19  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
  2 19  1  0
 12 15  1  0
  3 20  1  0
  3 21  2  0
 17 22  1  1
 16 23  1  6
 24 25  1  0
 24 26  2  0
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221801

   3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohexen-1-yl]triazol-1-yl]benzoic 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: 361.31

Molecular Weight (Monoisotopic): 361.0910

AlogP: -0.71

#Rotatable Bonds: 4

Polar Surface Area: 166.00

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.98

CX Basic pKa: ┄

CX LogP: -0.33

CX LogD: -7.00

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -0.25

References

1. 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