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

ID: ALA305669

PubChem CID: 44314838

Max Phase: Preclinical

Molecular Formula: C14H22N2O4

Molecular Weight: 282.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)c1cc(C2NCC(O)C2O)oc1C

Standard InChI:  InChI=1S/C14H22N2O4/c1-4-16(5-2)14(19)9-6-11(20-8(9)3)12-13(18)10(17)7-15-12/h6,10,12-13,15,17-18H,4-5,7H2,1-3H3

Standard InChI Key:  JMGMYORMUHCVGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    2.9375   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -2.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250   -2.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -3.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -0.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -0.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -4.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -4.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292    0.1000    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  9  1  0
 11  5  1  0
 12  8  1  0
 13  5  2  0
 14  9  1  0
 15 10  1  0
 16  6  1  0
 17 11  1  0
 18 11  1  0
 19 17  1  0
 20 18  1  0
  2  7  1  0
 10 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA305669

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

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: 282.34

Molecular Weight (Monoisotopic): 282.1580

AlogP: 0.44

#Rotatable Bonds: 4

Polar Surface Area: 85.94

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.17

CX Basic pKa: 7.68

CX LogP: -0.57

CX LogD: -1.03

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.75

Np Likeness Score: -0.17

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