1-{4-(p-Methoxyphenyl)butyl}-L-arabino-iminofuranose

ID: ALA3311516

PubChem CID: 102343111

Max Phase: Preclinical

Molecular Formula: C16H25NO4

Molecular Weight: 295.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCCC[C@@H]2N[C@@H](CO)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C16H25NO4/c1-21-12-8-6-11(7-9-12)4-2-3-5-13-15(19)16(20)14(10-18)17-13/h6-9,13-20H,2-5,10H2,1H3/t13-,14-,15-,16-/m0/s1

Standard InChI Key:  LSLFNXACKCUPBW-VGWMRTNUSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    9.3647   -8.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1392   -8.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6279   -8.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1533   -9.6121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3752   -9.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6737   -9.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3827   -7.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9599   -9.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2585   -9.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447   -9.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6980   -8.0767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4451   -8.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8620   -9.6371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8432   -9.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1316   -9.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4306   -9.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4426  -10.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1614  -11.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8594  -10.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417  -11.0836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273  -10.6867    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
  2  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  6
  3 12  1  6
 12 13  1  0
 10 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
 17 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3311516

   (2S,3S,4S,5S)-2-(hydroxymethyl)-5-[4-(4-methoxyphenyl)butyl]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: 295.38

Molecular Weight (Monoisotopic): 295.1784

AlogP: 0.46

#Rotatable Bonds: 7

Polar Surface Area: 81.95

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: 9.63

CX LogP: 0.99

CX LogD: -1.20

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: 1.28

References

1. Natori Y, Sakuma T, Yoshimura Y, Kinami K, Hirokami Y, Sato K, Adachi I, Kato A, Takahata H..  (2014)  Synthesis and biological evaluation of α-1-C-4'-arylbutyl-L-arabinoiminofuranoses, a new class of α-glucosidase inhibitors.,  24  (15): [PMID:24973028] [10.1016/j.bmcl.2014.06.001]

Source

Source(1):

• Scientific Literature