2-(4-Hydroxymethyl-5-methyl-furan-2-yl)-pyrrolidine-3,4-diol

ID: ALA83178

PubChem CID: 44319796

Max Phase: Preclinical

Molecular Formula: C10H15NO4

Molecular Weight: 213.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1oc(C2NCC(O)C2O)cc1CO

Standard InChI:  InChI=1S/C10H15NO4/c1-5-6(4-12)2-8(15-5)9-10(14)7(13)3-11-9/h2,7,9-14H,3-4H2,1H3

Standard InChI Key:  XVJUIKJDTLWLBB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    6.4167   -2.1167    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
    7.1750   -2.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000   -1.1167    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
    5.0792   -2.0417    0.0000 N   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
    5.4125   -3.3292    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
    5.8917   -4.0042    0.0000 O   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
    4.0917   -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
    8.4500   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  5  1  0
  5  1  2  0
  6  2  1  0
  7  3  1  0
  8  2  1  0
  9  8  1  0
 10  6  1  0
 11  8  1  0
 12  4  1  0
 13  9  1  0
 14  7  1  0
 15 12  1  0
  7  4  2  0
 10  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA83178

   2-[4-(Hydroxymethyl)-5-methylfuran-2-yl]pyrrolidine-3,4-diol

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: 213.23

Molecular Weight (Monoisotopic): 213.1001

AlogP: -0.55

#Rotatable Bonds: 2

Polar Surface Area: 85.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.15

CX Basic pKa: 8.10

CX LogP: -1.35

CX LogD: -2.13

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.53

Np Likeness Score: 1.01

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