5-(2-amino-5-(methoxycarbonyl)oxazol-4-yl)furan-2-ylphosphonic acid

ID: ALA3218223

PubChem CID: 90665562

Max Phase: Preclinical

Molecular Formula: C9H9N2O7P

Molecular Weight: 288.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1oc(N)nc1-c1ccc(P(=O)(O)O)o1

Standard InChI:  InChI=1S/C9H9N2O7P/c1-16-8(12)7-6(11-9(10)18-7)4-2-3-5(17-4)19(13,14)15/h2-3H,1H3,(H2,10,11)(H2,13,14,15)

Standard InChI Key:  IKAZYXVIVMAPCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    7.4537   -5.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2709   -5.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5253   -4.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8623   -4.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2036   -4.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3028   -4.3414    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.9094   -4.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8901   -3.6278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8806   -3.7558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4263   -4.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1720   -3.5666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3539   -3.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1026   -4.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663   -4.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728   -2.9062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7698   -5.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0636   -6.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4790   -6.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -6.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 11 12  2  0
 10 11  1  0
 12 13  1  0
 13 14  1  0
 14 10  2  0
 12 15  1  0
 16 17  1  0
 16 18  2  0
 14 16  1  0
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3218223

   [5-(2-Amino-5-methoxycarbonyl-1,3-oxazol-4-yl)furan-2-yl]phosphonic 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: 288.15

Molecular Weight (Monoisotopic): 288.0147

AlogP: 0.11

#Rotatable Bonds: 3

Polar Surface Area: 149.02

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.15

CX Basic pKa: ┄

CX LogP: -0.63

CX LogD: -4.00

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.53

Np Likeness Score: -0.14

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