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

ID: ALA3350284

PubChem CID: 513279

Max Phase: Preclinical

Molecular Formula: C12H17NO5

Molecular Weight: 255.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc([C@@H]2NC[C@@H](O)[C@H]2O)oc1C

Standard InChI:  InChI=1S/C12H17NO5/c1-3-17-12(16)7-4-9(18-6(7)2)10-11(15)8(14)5-13-10/h4,8,10-11,13-15H,3,5H2,1-2H3/t8-,10+,11-/m1/s1

Standard InChI Key:  HQEANUUDGAQVBA-DVVUODLYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    6.2326   -4.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2964   -5.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4212   -5.0676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5850   -6.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6070   -5.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0453   -6.2450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236   -5.9954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350   -7.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6070   -4.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487   -7.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2994   -6.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1577   -3.4991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716   -7.6388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4308   -4.1356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367   -8.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4308   -5.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8052   -3.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6290   -3.3618    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  1
  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
  8 13  1  6
 14  9  1  0
 10 15  1  6
 16  5  1  0
 17 14  1  0
 18 17  1  0
  2  6  1  0
 10 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3350284

   ethyl 5-[(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-2-methyl-3-furoate

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: 255.27

Molecular Weight (Monoisotopic): 255.1107

AlogP: 0.13

#Rotatable Bonds: 3

Polar Surface Area: 91.93

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.16

CX Basic pKa: 7.93

CX LogP: -0.22

CX LogD: -0.87

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.66

Np Likeness Score: 0.38

References

1. Moreno-Vargas AJ, Demange R, Fuentes J, Robina I, Vogel P..  (2002)  Synthesis of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic acid derivatives: new leads as selective beta-galactosidase inhibitors.,  12  (17): [PMID:12161128] [10.1016/s0960-894x(02)00397-9]

Source

Source(1):

• Scientific Literature