(2R,3R,4S)-2{{{(1R)-2-Hydroxy-1-[4-(prop-2-enyloxy)phenyl]-ethyl}amino}methyl}pyrrolidine-3,4-diol

ID: ALA1087105

PubChem CID: 44177400

Max Phase: Preclinical

Molecular Formula: C16H24N2O4

Molecular Weight: 308.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCOc1ccc([C@H](CO)NC[C@H]2NC[C@H](O)[C@@H]2O)cc1

Standard InChI:  InChI=1S/C16H24N2O4/c1-2-7-22-12-5-3-11(4-6-12)14(10-19)17-8-13-16(21)15(20)9-18-13/h2-6,13-21H,1,7-10H2/t13-,14+,15+,16-/m1/s1

Standard InChI Key:  VTILUTLLIVHFFV-FXUDXRNXSA-N

Molfile:  

     RDKit          2D

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   -2.3776   -9.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6628  -10.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -9.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -8.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6646   -8.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6670   -7.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9538   -7.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2381   -7.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3827   -7.1227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0960   -7.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117   -7.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0566   -6.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8815   -6.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1449   -7.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826   -7.6002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3593   -5.6538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5634   -5.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630  -10.8360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486  -11.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488  -12.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2344  -12.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  5  6  2  0
 12 11  1  1
 12 13  1  0
  6  1  1  0
  1  2  2  0
  6  7  1  0
  3  4  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  7  8  1  0
 14 17  1  6
 13 18  1  6
  8  9  1  0
  3 19  1  0
  4  5  1  0
 19 20  1  0
  7 10  1  1
 20 21  1  0
  2  3  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1087105

   (2R,3R,4S)-2-[[[(1R)-2-hydroxy-1-(4-prop-2-enoxyphenyl)ethyl]amino]methyl]pyrrolidine-3,4-diol

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: -0.43

#Rotatable Bonds: 8

Polar Surface Area: 93.98

Molecular Species: BASE

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.34

CX Basic pKa: 9.13

CX LogP: -0.26

CX LogD: -1.99

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.42

Np Likeness Score: 0.67

References

1. Bello C, Cea M, Dal Bello G, Garuti A, Rocco I, Cirmena G, Moran E, Nahimana A, Duchosal MA, Fruscione F, Pronzato P, Grossi F, Patrone F, Ballestrero A, Dupuis M, Sordat B, Nencioni A, Vogel P..  (2010)  Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as alpha-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies.,  18  (9): [PMID:20346684] [10.1016/j.bmc.2010.03.009]

Source

Source(1):

• Scientific Literature