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

ID: ALA4101240

PubChem CID: 137659612

Max Phase: Preclinical

Molecular Formula: C13H16N4O8

Molecular Weight: 356.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C13H16N4O8/c18-5-10-12(20)11(19)9(15-10)4-14-13(21)6-1-7(16(22)23)3-8(2-6)17(24)25/h1-3,9-12,15,18-20H,4-5H2,(H,14,21)/t9-,10+,11+,12-/m0/s1

Standard InChI Key:  MLTRZBZSUMDYKY-QCNOEVLYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    3.5083  -16.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333  -16.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5901  -15.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9208  -15.3916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557  -15.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710  -15.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2992  -14.8169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225  -17.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8174  -17.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3751  -15.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5477  -14.8178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3327  -14.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5053  -13.7572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9450  -15.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7703  -15.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3817  -16.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1677  -16.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3386  -15.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7258  -14.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1239  -15.1530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2937  -14.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7382  -15.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2060  -17.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8181  -17.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4210  -17.5405    0.0000 O   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
 20 21  2  0
 20 22  1  0
 18 20  1  0
 23 24  2  0
 23 25  1  0
 16 23  1  0
M  CHG  4  20   1  22  -1  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4101240

   ---

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: 356.29

Molecular Weight (Monoisotopic): 356.0968

AlogP: -1.71

#Rotatable Bonds: 6

Polar Surface Area: 188.10

Molecular Species: BASE

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.28

CX Basic pKa: 8.67

CX LogP: -1.44

CX LogD: -2.73

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.29

Np Likeness Score: -0.01

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