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

ID: ALA82816

PubChem CID: 44319677

Max Phase: Preclinical

Molecular Formula: C10H13NO5

Molecular Weight: 227.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H13NO5/c1-4-5(10(14)15)2-7(16-4)8-9(13)6(12)3-11-8/h2,6,8-9,11-13H,3H2,1H3,(H,14,15)

Standard InChI Key:  ADUVJHVZQGZMPK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  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
    5.8917   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500   -0.2625    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
  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
  2  6  1  0
 11 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA82816

   5-(3,4-Dihydroxypyrrolidin-2-yl)-2-methylfuran-3-carboxylic acid

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: 227.22

Molecular Weight (Monoisotopic): 227.0794

AlogP: -0.35

#Rotatable Bonds: 2

Polar Surface Area: 102.93

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.94

CX Basic pKa: 8.13

CX LogP: -3.39

CX LogD: -3.45

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.55

Np Likeness Score: 0.79

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