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

ID: ALA4102645

PubChem CID: 137657837

Max Phase: Preclinical

Molecular Formula: C12H24N2O7

Molecular Weight: 308.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H24N2O7/c1-19-7-21-3-2-20-6-10(16)13-4-8-11(17)12(18)9(5-15)14-8/h8-9,11-12,14-15,17-18H,2-7H2,1H3,(H,13,16)/t8-,9+,11+,12-/m0/s1

Standard InChI Key:  KSSLJLGDPKLROQ-SPFNVWMYSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   33.4787   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3037   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5606   -3.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8912   -2.9459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2262   -3.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4415   -3.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2696   -2.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9930   -4.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7879   -4.8847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3456   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5182   -2.3719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3031   -2.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4758   -1.3114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9154   -2.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7428   -3.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3552   -4.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1824   -4.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7948   -5.3902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6222   -6.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2345   -6.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0619   -7.5565    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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102645

   ---

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: 308.33

Molecular Weight (Monoisotopic): 308.1584

AlogP: -3.21

#Rotatable Bonds: 10

Polar Surface Area: 129.51

Molecular Species: BASE

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 8.67

CX LogP: -3.33

CX LogD: -4.62

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.21

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