(1R,4R,5R)-3-(1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid

ID: ALA3221799

PubChem CID: 90668066

Max Phase: Preclinical

Molecular Formula: C15H14FN3O5

Molecular Weight: 335.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cn(-c3ccc(F)cc3)nn2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C15H14FN3O5/c16-8-1-3-9(4-2-8)19-7-11(17-18-19)10-5-15(24,14(22)23)6-12(20)13(10)21/h1-5,7,12-13,20-21,24H,6H2,(H,22,23)/t12-,13-,15+/m1/s1

Standard InChI Key:  XNCBIIULCUUSQD-NFAWXSAZSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   14.5361   -0.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3256   -1.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1171   -1.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8143   -2.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8132   -3.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5212   -3.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2309   -3.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2281   -2.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5195   -2.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9362   -2.2300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6840   -2.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2285   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8172   -1.2440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0186   -1.4170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0389   -2.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3727   -2.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1820   -2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6634   -2.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5144   -1.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6991   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3286   -0.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5143   -3.6138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8932   -3.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1052   -3.8690    0.0000 F   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
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221799

   (1R,4R,5R)-3-[1-(4-fluorophenyl)triazol-4-yl]-1,4,5-trihydroxycyclohex-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: 335.29

Molecular Weight (Monoisotopic): 335.0917

AlogP: -0.27

#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: 3.04

CX Basic pKa: ┄

CX LogP: 0.15

CX LogD: -3.32

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -0.48

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