5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-4-methoxy-5H-furan-2-one

ID: ALA45237

PubChem CID: 14351106

Max Phase: Preclinical

Molecular Formula: C10H14O6

Molecular Weight: 230.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=C(O)C(=O)OC1C1COC(C)(C)O1

Standard InChI:  InChI=1S/C10H14O6/c1-10(2)14-4-5(16-10)7-8(13-3)6(11)9(12)15-7/h5,7,11H,4H2,1-3H3

Standard InChI Key:  IRFTYLPNPVDEBK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    6.3667   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -2.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -1.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -2.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4667   -2.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -4.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -4.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -4.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  1  0
  6  3  1  0
  7  6  1  0
  8  7  1  0
  9 10  1  0
 10  6  1  0
 11  4  2  0
 12  1  1  0
 13  2  1  0
 14  8  1  0
 15  8  1  0
 16 13  1  0
  5  3  1  0
  8  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA45237

   2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-3-methoxy-2H-furan-5-one

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: 230.22

Molecular Weight (Monoisotopic): 230.0790

AlogP: 0.48

#Rotatable Bonds: 2

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.25

CX Basic pKa: ┄

CX LogP: -0.10

CX LogD: -0.16

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.70

Np Likeness Score: 1.91

References

1. Abell AD, Ratcliffe MJ, Gerrard J..  (1998)  Ascorbic acid-based inhibitors of alpha-amylases.,  8  (13): [PMID:9873419] [10.1016/s0960-894x(98)00298-4]

2. Al-Asri J, Fazekas E, Lehoczki G, Perdih A, Görick C, Melzig MF, Gyémánt G, Wolber G, Mortier J..  (2015)  From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.,  23  (20): [PMID:26395057] [10.1016/j.bmc.2015.09.007]

Source

Source(1):

• Scientific Literature