(2-methyl-5-(trifluoromethyl)oxazole-4-carbonyloxy)methylphosphonic acid

ID: ALA3218454

PubChem CID: 90665716

Max Phase: Preclinical

Molecular Formula: C7H7F3NO6P

Molecular Weight: 289.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(C(=O)OCP(=O)(O)O)c(C(F)(F)F)o1

Standard InChI:  InChI=1S/C7H7F3NO6P/c1-3-11-4(5(17-3)7(8,9)10)6(12)16-2-18(13,14)15/h2H2,1H3,(H2,13,14,15)

Standard InChI Key:  DHBCTFOLKBUHOI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    6.8207   -4.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292   -4.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973   -3.3023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3106   -3.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8550   -3.7575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3617   -4.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0295   -2.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7893   -5.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5436   -4.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2358   -4.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9513   -4.2127    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.6505   -4.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4108   -3.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4076   -3.5282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1402   -5.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3482   -5.3878    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7106   -5.7716    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9238   -5.9721    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  2  0
  2  3  1  0
  4  5  1  0
  5  6  1  0
  6  2  2  0
  4  7  1  0
  1  8  2  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  6 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3218454

   [2-Methyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]oxymethylphosphonic 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: 289.10

Molecular Weight (Monoisotopic): 288.9963

AlogP: 1.29

#Rotatable Bonds: 3

Polar Surface Area: 109.86

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.34

CX Basic pKa: ┄

CX LogP: -0.13

CX LogD: -2.15

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.64

Np Likeness Score: -0.55

References

1. Dang Q, Kasibthatla SR, Jiang T, Taplin F, Gibson T, Potter SC, van Poelje PD, Erion MD.  (2011)  Oxazole phosphonic acids as fructose 1,6-bisphosphatase inhibitors with potent glucose-lowering activity,  2  (4): [10.1039/C0MD00269K]

Source

Source(1):

• Scientific Literature