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

ID: ALA75265

PubChem CID: 44314840

Max Phase: Preclinical

Molecular Formula: C13H20N2O4

Molecular Weight: 268.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1oc(C2NCC(O)C2O)cc1C(=O)NC(C)C

Standard InChI:  InChI=1S/C13H20N2O4/c1-6(2)15-13(18)8-4-10(19-7(8)3)11-12(17)9(16)5-14-11/h4,6,9,11-12,14,16-17H,5H2,1-3H3,(H,15,18)

Standard InChI Key:  VHRUAYMCMAKGDX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    2.9792   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -1.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -2.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -1.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -0.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875   -4.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917    0.4250    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  1  0
  6  1  2  0
  7  6  1  0
  8  4  1  0
  9  4  1  0
 10  5  1  0
 11  9  1  0
 12  8  1  0
 13  5  2  0
 14  9  1  0
 15 11  1  0
 16  6  1  0
 17 10  1  0
 18 17  1  0
 19 17  1  0
  2  7  1  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA75265

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

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: 268.31

Molecular Weight (Monoisotopic): 268.1423

AlogP: 0.09

#Rotatable Bonds: 3

Polar Surface Area: 94.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.15

CX Basic pKa: 7.68

CX LogP: -0.73

CX LogD: -1.19

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.62

Np Likeness Score: 0.00

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