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

ID: ALA4102996

PubChem CID: 137657710

Max Phase: Preclinical

Molecular Formula: C15H22N2O6

Molecular Weight: 326.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(C(=O)NC[C@@H]2N[C@H](CO)[C@H](O)[C@@H]2O)c1

Standard InChI:  InChI=1S/C15H22N2O6/c1-22-8-3-4-12(23-2)9(5-8)15(21)16-6-10-13(19)14(20)11(7-18)17-10/h3-5,10-11,13-14,17-20H,6-7H2,1-2H3,(H,16,21)/t10-,11+,13+,14-/m0/s1

Standard InChI Key:  QDGATUZKZITKLK-UNJBNNCHSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.9415  -11.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587  -11.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0130  -11.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3501  -10.5409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6913  -11.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140  -10.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7438   -9.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603  -12.4603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2382  -12.4615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7906  -10.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9616   -9.9725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7391   -9.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9101   -8.9220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3457  -10.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1726  -11.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7783  -11.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5568  -11.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7261  -10.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1191  -10.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2876   -9.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0644   -8.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6069  -12.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292  -12.6658    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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 19 20  1  0
 20 21  1  0
 16 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102996

   ---

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: 326.35

Molecular Weight (Monoisotopic): 326.1478

AlogP: -1.51

#Rotatable Bonds: 6

Polar Surface Area: 120.28

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.09

CX Basic pKa: 8.67

CX LogP: -1.63

CX LogD: -2.92

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.43

Np Likeness Score: 0.37

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