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

ID: ALA3350286

PubChem CID: 513284

Max Phase: Preclinical

Molecular Formula: C13H20N2O4

Molecular Weight: 268.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1oc([C@H]2NC[C@@H](O)[C@H]2O)cc1C(=O)NC(C)C

Standard InChI:  InChI=1S/C13H20N2O4/c1-6(2)15-13(18)8-4-10(19-7(8)3)11-12(17)9(16)5-14-11/h4,6,9,11-12,14,16-17H,5H2,1-3H3,(H,15,18)/t9-,11-,12-/m1/s1

Standard InChI Key:  VHRUAYMCMAKGDX-YUSALJHKSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    2.9744   -1.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0466   -2.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271   -3.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3487   -1.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570   -2.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -3.1074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658   -2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2854   -3.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1725   -1.0026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -4.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416   -3.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -0.3619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9218   -4.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1872   -4.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808   -2.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5426   -0.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3663   -0.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0851    0.4243    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  5  1  0
 11  9  1  0
 12  8  1  0
 13  5  2  0
  9 14  1  6
 11 15  1  6
 16  6  1  0
 17 10  1  0
 18 17  1  0
 19 17  1  0
  2  7  1  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3350286

   5-[(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-N-isopropyl-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: 268.31

Molecular Weight (Monoisotopic): 268.1423

AlogP: 0.09

#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: 7.68

CX LogP: -0.73

CX LogD: -1.19

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.62

Np Likeness Score: 0.00

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