(5-phenyloxazole-4-carbonyloxy)methylphosphonic acid

ID: ALA3218455

PubChem CID: 90665717

Max Phase: Preclinical

Molecular Formula: C11H10NO6P

Molecular Weight: 283.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(OCP(=O)(O)O)c1ncoc1-c1ccccc1

Standard InChI:  InChI=1S/C11H10NO6P/c13-11(18-7-19(14,15)16)9-10(17-6-12-9)8-4-2-1-3-5-8/h1-6H,7H2,(H2,14,15,16)

Standard InChI Key:  PPWFDBDMAAIDKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  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
    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
    4.3486   -5.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -6.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976   -6.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4930   -6.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7110   -5.7645    0.0000 C   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
  1  7  2  0
  1  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3218455

   (5-Phenyl-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: 283.18

Molecular Weight (Monoisotopic): 283.0246

AlogP: 1.63

#Rotatable Bonds: 4

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: 0.41

CX LogD: -1.61

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.65

Np Likeness Score: -0.31

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