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

ID: ALA2114149

PubChem CID: 513283

Max Phase: Preclinical

Molecular Formula: C14H22N2O4

Molecular Weight: 282.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H22N2O4/c1-4-16(5-2)14(19)9-6-11(20-8(9)3)12-13(18)10(17)7-15-12/h6,10,12-13,15,17-18H,4-5,7H2,1-3H3/t10-,12-,13-/m1/s1

Standard InChI Key:  JMGMYORMUHCVGM-RAIGVLPGSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    2.9321   -1.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0005   -2.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -1.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -2.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3064   -0.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3106   -2.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -2.7824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5240   -2.5329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394   -3.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299   -0.6780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573   -0.0291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8758   -4.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414   -4.6415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1341   -2.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5791   -1.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960    0.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4026   -1.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194    0.0998    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  6
  5  1  1  0
  6  1  2  0
  7  6  1  0
  8  4  1  0
  9  4  1  0
 10  9  1  0
 11  5  1  0
 12  8  1  0
 13  5  2  0
  9 14  1  6
 10 15  1  6
 16  6  1  0
 17 11  1  0
 18 11  1  0
 19 17  1  0
 20 18  1  0
  2  7  1  0
 10 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2114149

   5-[(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-N,N-diethyl-2-methyl-3-furamide

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: 282.34

Molecular Weight (Monoisotopic): 282.1580

AlogP: 0.44

#Rotatable Bonds: 4

Polar Surface Area: 85.94

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.17

CX Basic pKa: 7.68

CX LogP: -0.57

CX LogD: -1.03

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.75

Np Likeness Score: -0.17

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