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

ID: ALA3221800

PubChem CID: 90668067

Max Phase: Preclinical

Molecular Formula: C15H14N4O7

Molecular Weight: 362.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cn(-c3cccc([N+](=O)[O-])c3)nn2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C15H14N4O7/c20-12-6-15(24,14(22)23)5-10(13(12)21)11-7-18(17-16-11)8-2-1-3-9(4-8)19(25)26/h1-5,7,12-13,20-21,24H,6H2,(H,22,23)/t12-,13-,15+/m1/s1

Standard InChI Key:  VCACPDOUGRGMGJ-NFAWXSAZSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.7917   -5.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5812   -6.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727   -6.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -7.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9343   -8.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309   -8.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4865   -8.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837   -7.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291   -7.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918   -7.2529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -7.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841   -6.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0728   -6.2668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742   -6.4399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2945   -7.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283   -7.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4376   -7.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9190   -7.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700   -6.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547   -6.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5842   -5.4718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699   -8.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1489   -8.4679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244   -9.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4863  -10.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9364  -10.1229    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  2  0
 24 26  1  0
  6 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3221800

   (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)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: 362.30

Molecular Weight (Monoisotopic): 362.0862

AlogP: -0.50

#Rotatable Bonds: 4

Polar Surface Area: 171.84

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.92

CX Basic pKa: ┄

CX LogP: -0.05

CX LogD: -3.53

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: -0.67

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