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

ID: ALA4100689

PubChem CID: 137658863

Max Phase: Preclinical

Molecular Formula: C15H22N2O5

Molecular Weight: 310.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CC(=O)NC[C@@H]2N[C@H](CO)[C@H](O)[C@@H]2O)c1

Standard InChI:  InChI=1S/C15H22N2O5/c1-22-10-4-2-3-9(5-10)6-13(19)16-7-11-14(20)15(21)12(8-18)17-11/h2-5,11-12,14-15,17-18,20-21H,6-8H2,1H3,(H,16,19)/t11-,12+,14+,15-/m0/s1

Standard InChI Key:  RCMAJSODMLOSAW-MXYBEHONSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   23.8677  -15.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6849  -15.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9393  -14.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2763  -14.2472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6176  -14.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8403  -14.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6700  -13.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3865  -16.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1645  -16.1677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7168  -14.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8878  -13.6788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6654  -13.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8364  -12.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2719  -13.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1009  -14.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3236  -15.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1524  -15.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7593  -16.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5401  -16.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7076  -15.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1485  -16.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9803  -17.4577    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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100689

   ---

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: 310.35

Molecular Weight (Monoisotopic): 310.1529

AlogP: -1.59

#Rotatable Bonds: 6

Polar Surface Area: 111.05

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: 8.67

CX LogP: -1.50

CX LogD: -2.78

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.43

Np Likeness Score: 0.28

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