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

ID: ALA87234

PubChem CID: 44319670

Max Phase: Preclinical

Molecular Formula: C12H18N2O4

Molecular Weight: 254.29

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H18N2O4/c1-3-13-12(17)7-4-9(18-6(7)2)10-11(16)8(15)5-14-10/h4,8,10-11,14-16H,3,5H2,1-2H3,(H,13,17)

Standard InChI Key:  GCYDGJRKTRAQRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    7.3000   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1750   -2.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -2.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375    0.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500   -0.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -3.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5917    0.5875    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  9  1  0
 14  8  1  0
 15 10  1  0
 16  5  1  0
 17 13  1  0
 18 17  1  0
  2  6  1  0
 11 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA87234

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

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: 254.29

Molecular Weight (Monoisotopic): 254.1267

AlogP: -0.30

#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: 13.14

CX Basic pKa: 7.68

CX LogP: -1.15

CX LogD: -1.61

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.59

Np Likeness Score: -0.02

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