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

ID: ALA430644

PubChem CID: 44319846

Max Phase: Preclinical

Molecular Formula: C16H18N2O4

Molecular Weight: 302.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1oc(C2NCC(O)C2O)cc1C(=O)Nc1ccccc1

Standard InChI:  InChI=1S/C16H18N2O4/c1-9-11(16(21)18-10-5-3-2-4-6-10)7-13(22-9)14-15(20)12(19)8-17-14/h2-7,12,14-15,17,19-20H,8H2,1H3,(H,18,21)

Standard InChI Key:  XPEGIGALEVPIAG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  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
    7.6292   -0.3542    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
    8.4500   -0.2625    0.0000 N   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
    5.8917   -4.0042    0.0000 O   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
    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
    9.5917    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2875    1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9250    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292    2.0083    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 10  1  0
 16 11  1  0
 17  6  1  0
 18 15  2  0
 19 15  1  0
 20 19  2  0
 21 18  1  0
 22 20  1  0
  2  7  1  0
 12 11  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA430644

   5-(3,4-dihydroxypyrrolidin-2-yl)-2-methyl-N-phenylfuran-3-carboxamide

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: 302.33

Molecular Weight (Monoisotopic): 302.1267

AlogP: 1.21

#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: 7.66

CX LogP: 0.51

CX LogD: 0.06

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: -0.28

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