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

ID: ALA3221803

PubChem CID: 90668070

Max Phase: Preclinical

Molecular Formula: C14H14N4O5

Molecular Weight: 318.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cn(-c3cccnc3)nn2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C14H14N4O5/c19-11-5-14(23,13(21)22)4-9(12(11)20)10-7-18(17-16-10)8-2-1-3-15-6-8/h1-4,6-7,11-12,19-20,23H,5H2,(H,21,22)/t11-,12-,14+/m1/s1

Standard InChI Key:  KHTMEUNZXUIIKO-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   14.0161  -11.1188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8056  -11.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5971  -11.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2943  -13.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2932  -13.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0012  -14.3242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7109  -13.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7080  -13.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9994  -12.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4161  -12.6843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1639  -13.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7084  -12.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2972  -11.6983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4985  -11.8713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5188  -12.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8526  -13.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6619  -13.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1434  -12.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9943  -11.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1791  -12.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8086  -10.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9943  -14.0680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3732  -13.8993    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
M  END

Alternative Forms

1. Parent:

   

   ALA3221803

   (1R,4R,5R)-1,4,5-trihydroxy-3-(1-pyridin-3-yltriazol-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: 318.29

Molecular Weight (Monoisotopic): 318.0964

AlogP: -1.01

#Rotatable Bonds: 3

Polar Surface Area: 141.59

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.00

CX Basic pKa: 4.80

CX LogP: -2.37

CX LogD: -4.52

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.56

Np Likeness Score: -0.28

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