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

ID: ALA4091521

PubChem CID: 137656241

Max Phase: Preclinical

Molecular Formula: C13H24N2O4

Molecular Weight: 272.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O)C1CCCCC1

Standard InChI:  InChI=1S/C13H24N2O4/c16-7-10-12(18)11(17)9(15-10)6-14-13(19)8-4-2-1-3-5-8/h8-12,15-18H,1-7H2,(H,14,19)/t9-,10+,11+,12-/m0/s1

Standard InChI Key:  WDLVELQAOUGGPM-QCNOEVLYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   13.5332   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3582   -4.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6151   -3.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9457   -3.4458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2807   -3.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4960   -3.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3241   -2.8711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0474   -5.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8424   -5.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4000   -3.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5726   -2.8720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3577   -2.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5303   -1.8114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9699   -3.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7906   -3.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3990   -4.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1855   -4.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3604   -3.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7485   -2.9191    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
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091521

   ---

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: 272.35

Molecular Weight (Monoisotopic): 272.1736

AlogP: -1.26

#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: -1.06

CX LogD: -2.35

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.44

Np Likeness Score: 0.42

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