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

ID: ALA4097834

PubChem CID: 137661105

Max Phase: Preclinical

Molecular Formula: C16H24N2O4

Molecular Weight: 308.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C(=O)NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O)c1ccccc1

Standard InChI:  InChI=1S/C16H24N2O4/c1-2-11(10-6-4-3-5-7-10)16(22)17-8-12-14(20)15(21)13(9-19)18-12/h3-7,11-15,18-21H,2,8-9H2,1H3,(H,17,22)/t11?,12-,13+,14+,15-/m0/s1

Standard InChI Key:  HKHAAGCWKAKGFT-CMAIEHALSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    4.3210   -4.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1460   -4.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029   -3.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7335   -3.3085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685   -3.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837   -3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118   -2.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8352   -5.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6302   -5.2474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1879   -3.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3605   -2.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1456   -2.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3182   -1.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7579   -3.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5428   -2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852   -3.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1553   -3.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8005   -4.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6276   -4.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2404   -5.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0286   -5.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1977   -4.3864    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 16  1  0
 15 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097834

   ---

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: 308.38

Molecular Weight (Monoisotopic): 308.1736

AlogP: -0.65

#Rotatable Bonds: 6

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: -0.35

CX LogD: -1.64

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.48

Np Likeness Score: 0.43

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