5-(3,4-Dihydroxy-pyrrolidin-2-yl)-2-methyl-furan-3-carboxylic acid ethyl ester

ID: ALA306321

PubChem CID: 44314837

Max Phase: Preclinical

Molecular Formula: C12H17NO5

Molecular Weight: 255.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(C2NCC(O)C2O)oc1C

Standard InChI:  InChI=1S/C12H17NO5/c1-3-17-12(16)7-4-9(18-6(7)2)10-11(15)8(14)5-13-10/h4,8,10-11,13-15H,3,5H2,1-2H3

Standard InChI Key:  HQEANUUDGAQVBA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    6.2417   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -5.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -5.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -6.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -6.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -7.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -6.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -3.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -7.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -4.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -8.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6417   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  1  1  0
  4  2  1  0
  5  1  2  0
  6  5  1  0
  7  4  1  0
  8  4  1  0
  9  1  1  0
 10  8  1  0
 11  7  1  0
 12  9  2  0
 13  8  1  0
 14  9  1  0
 15 10  1  0
 16  5  1  0
 17 14  1  0
 18 17  1  0
  2  6  1  0
 10 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA306321

   5-(3,4-Dihydroxy-pyrrolidin-2-yl)-2-methyl-furan-3-carboxylic acid ethyl ester

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: 255.27

Molecular Weight (Monoisotopic): 255.1107

AlogP: 0.13

#Rotatable Bonds: 3

Polar Surface Area: 91.93

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.16

CX Basic pKa: 7.93

CX LogP: -0.22

CX LogD: -0.87

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.66

Np Likeness Score: 0.38

References

1. Robina I, Moreno-Vargas AJ, Fernández-Bolaños JG, Fuentes J, Demange R, Vogel P..  (2001)  New leads for selective inhibitors of alpha-L-fucosidases. Synthesis and glycosidase inhibitory activities of [(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives.,  11  (18): [PMID:11549468] [10.1016/s0960-894x(01)00497-8]

Source

Source(1):

• Scientific Literature