N-(((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide

ID: ALA4095251

PubChem CID: 137652643

Max Phase: Preclinical

Molecular Formula: C17H24N2O4

Molecular Weight: 320.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O)C1CCc2ccccc2C1

Standard InChI:  InChI=1S/C17H24N2O4/c20-9-14-16(22)15(21)13(19-14)8-18-17(23)12-6-5-10-3-1-2-4-11(10)7-12/h1-4,12-16,19-22H,5-9H2,(H,18,23)/t12?,13-,14+,15+,16-/m0/s1

Standard InChI Key:  HFCOEKJZYDAAPO-GZPFGDLZSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   14.1564   -4.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9736   -4.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2279   -3.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5650   -2.7529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9062   -3.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1289   -2.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9586   -2.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6752   -4.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4531   -4.6734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0055   -2.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1765   -2.1844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9540   -1.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1250   -1.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5606   -2.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3829   -3.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9378   -2.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3318   -2.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7647   -3.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9871   -3.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8121   -4.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4138   -5.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1932   -4.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3645   -4.1287    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 17  1  0
 15 19  1  0
 18 16  1  0
 16 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095251

   ---

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: 320.39

Molecular Weight (Monoisotopic): 320.1736

AlogP: -1.04

#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: -0.30

CX LogD: -1.59

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.49

Np Likeness Score: 0.52

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