(1S)-N-(((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxamide

ID: ALA4097678

PubChem CID: 137661333

Max Phase: Preclinical

Molecular Formula: C16H26N2O5

Molecular Weight: 326.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C2CC[C@@]1(C(=O)NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O)C(=O)C2

Standard InChI:  InChI=1S/C16H26N2O5/c1-15(2)8-3-4-16(15,11(20)5-8)14(23)17-6-9-12(21)13(22)10(7-19)18-9/h8-10,12-13,18-19,21-22H,3-7H2,1-2H3,(H,17,23)/t8?,9-,10+,12+,13-,16-/m0/s1

Standard InChI Key:  JPTNYUKGEHEZRF-ZNOVDMIISA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   25.5599  -10.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7745   -9.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1084   -9.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9692  -10.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7864  -10.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0408   -9.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3778   -8.9478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7191   -9.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9418   -9.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7715   -8.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4880  -10.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2660  -10.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8183   -9.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9893   -8.3794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7669   -8.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9379   -7.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3734   -8.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1967   -9.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7993  -10.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5785   -9.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7516   -8.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1456   -8.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3164   -7.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  8  9  1  1
  9 10  1  0
  4 11  1  1
  5 12  1  1
  6 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  2  0
 17 15  1  6
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 17  2  1  0
  2 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097678

   ---

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: 326.39

Molecular Weight (Monoisotopic): 326.1842

AlogP: -1.45

#Rotatable Bonds: 4

Polar Surface Area: 118.89

Molecular Species: BASE

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 8.57

CX LogP: -1.21

CX LogD: -2.40

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.40

Np Likeness Score: 1.55

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