(3aS,6S,6aS)-3-Hydroxymethyl-3a,5,6,6a-tetrahydro-furo[2,3-d]isoxazole-5,6-diol

ID: ALA96060

PubChem CID: 480948

Max Phase: Preclinical

Molecular Formula: C6H9NO5

Molecular Weight: 175.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCC1=NO[C@H]2[C@H](O)C(O)O[C@@H]12

Standard InChI:  InChI=1S/C6H9NO5/c8-1-2-4-5(12-7-2)3(9)6(10)11-4/h3-6,8-10H,1H2/t3-,4-,5-,6?/m0/s1

Standard InChI Key:  ZGKWLIDXNPUSOH-NNXAEHONSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  1  0  0  0  0  0999 V2000
    0.7292   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -3.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -4.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -4.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -3.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -2.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2975   -2.0785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4173   -4.7668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  4  1  1  0
  5  6  1  0
  1  6  1  0
  7  2  1  0
  8  4  1  0
  4  9  1  6
  8 10  1  0
 11  7  1  0
 12 11  1  0
  8  3  1  0
  7  5  2  0
  2 13  1  6
  1 14  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA96060

   (3aS,6S,6aS)-3-(hydroxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d]isoxazole-5,6-diol

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: 175.14

Molecular Weight (Monoisotopic): 175.0481

AlogP: -2.19

#Rotatable Bonds: 1

Polar Surface Area: 91.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.29

CX Basic pKa: 0.51

CX LogP: -1.56

CX LogD: -1.56

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.42

Np Likeness Score: 1.83

References

1. Schaller C, Demange R, Picasso S, Vogel P..  (1999)  Specific, uncompetitive inhibition of beta-galactosidases by a 5,6-isopropylidenedioxyfuro[2,3-d]isoxazole-3-methanol derivative.,  9  (2): [PMID:10021944] [10.1016/s0960-894x(98)00722-7]

Source

Source(1):

• Scientific Literature