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

ID: ALA3221802

PubChem CID: 90668069

Max Phase: Preclinical

Molecular Formula: C15H15N3O6

Molecular Weight: 333.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cn(-c3ccccc3O)nn2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C15H15N3O6/c19-11-4-2-1-3-10(11)18-7-9(16-17-18)8-5-15(24,14(22)23)6-12(20)13(8)21/h1-5,7,12-13,19-21,24H,6H2,(H,22,23)/t12-,13-,15+/m1/s1

Standard InChI Key:  CSQYQQQDOOBJDG-NFAWXSAZSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    5.2375  -11.9318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0270  -12.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8185  -12.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4897  -13.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886  -14.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226  -15.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9323  -14.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294  -13.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208  -13.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375  -13.4974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853  -13.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9298  -13.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185  -12.5113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7199  -12.6844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402  -13.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740  -14.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833  -14.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3648  -13.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157  -12.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4005  -13.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0299  -11.7163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2157  -14.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5946  -14.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2184  -12.6827    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
  9 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221802

   (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)triazol-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: 333.30

Molecular Weight (Monoisotopic): 333.0961

AlogP: -0.70

#Rotatable Bonds: 3

Polar Surface Area: 148.93

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.99

CX Basic pKa: ┄

CX LogP: -0.29

CX LogD: -3.77

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.49

Np Likeness Score: 0.17

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