(2-amino-5-isopropyloxazole-4-carbonyloxy)methylphosphonic acid

ID: ALA3218451

PubChem CID: 22280713

Max Phase: Preclinical

Molecular Formula: C8H13N2O6P

Molecular Weight: 264.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1oc(N)nc1C(=O)OCP(=O)(O)O

Standard InChI:  InChI=1S/C8H13N2O6P/c1-4(2)6-5(10-8(9)16-6)7(11)15-3-17(12,13)14/h4H,3H2,1-2H3,(H2,9,10)(H2,12,13,14)

Standard InChI Key:  JLMJESVNSZQEKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  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 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7106   -5.7716    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
  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
M  END

Alternative Forms

1. Parent:

   

   ALA3218451

   (2-Amino-5-propan-2-yl-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: 264.17

Molecular Weight (Monoisotopic): 264.0511

AlogP: 0.67

#Rotatable Bonds: 4

Polar Surface Area: 135.88

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.42

CX Basic pKa: 0.57

CX LogP: -0.07

CX LogD: -2.18

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.53

Np Likeness Score: -0.05

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