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

ID: ALA4092796

PubChem CID: 137654205

Max Phase: Preclinical

Molecular Formula: C14H26N2O4

Molecular Weight: 286.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CC1CCCCC1)NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H26N2O4/c17-8-11-14(20)13(19)10(16-11)7-15-12(18)6-9-4-2-1-3-5-9/h9-11,13-14,16-17,19-20H,1-8H2,(H,15,18)/t10-,11+,13+,14-/m0/s1

Standard InChI Key:  YRBIAHWZUURQML-UNJBNNCHSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   16.8226  -11.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6397  -11.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8941  -10.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2311  -10.0746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5724  -10.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7951  -10.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6248   -9.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3414  -11.9939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1193  -11.9951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6717  -10.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8427   -9.5061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6202   -9.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7912   -8.4556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2267   -9.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0043   -9.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6092  -10.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3840   -9.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5592   -9.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9532   -8.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1721   -8.7530    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  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092796

   ---

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: 286.37

Molecular Weight (Monoisotopic): 286.1893

AlogP: -0.87

#Rotatable Bonds: 5

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: -0.87

CX LogD: -2.16

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.45

Np Likeness Score: 0.60

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