N-(((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)-4-methylbenzamide

ID: ALA4103974

PubChem CID: 137656921

Max Phase: Preclinical

Molecular Formula: C14H20N2O4

Molecular Weight: 280.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)NC[C@@H]2N[C@H](CO)[C@H](O)[C@@H]2O)cc1

Standard InChI:  InChI=1S/C14H20N2O4/c1-8-2-4-9(5-3-8)14(20)15-6-10-12(18)13(19)11(7-17)16-10/h2-5,10-13,16-19H,6-7H2,1H3,(H,15,20)/t10-,11+,12+,13-/m0/s1

Standard InChI Key:  YCIUFCZMOCUBMS-LOWDOPEQSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   34.0207   -9.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8379   -9.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0923   -9.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4293   -8.5764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7706   -9.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9933   -8.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8230   -8.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5395  -10.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3175  -10.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8698   -8.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0408   -8.0080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8184   -7.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9894   -6.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4249   -8.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2518   -9.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8575   -9.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6360   -9.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8054   -8.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1983   -8.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2433   -9.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  1  1
  6  7  1  0
  1  8  1  1
  2  9  1  1
  3 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103974

   ---

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: 280.32

Molecular Weight (Monoisotopic): 280.1423

AlogP: -1.22

#Rotatable Bonds: 4

Polar Surface Area: 101.82

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 8.67

CX LogP: -0.81

CX LogD: -2.09

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.48

Np Likeness Score: 0.40

References

1. Cheng WC, Wang JH, Yun WY, Li HY, Hu JM..  (2017)  Rapid preparation of (3R,4S,5R) polyhydroxylated pyrrolidine-based libraries to discover a pharmacological chaperone for treatment of Fabry disease.,  126  [PMID:27744182] [10.1016/j.ejmech.2016.10.004]

Source

Source(1):

• Scientific Literature