1-{4-(4-Methylphenyl)butyl}-L-arabino-iminofuranose

ID: ALA3311515

PubChem CID: 118707314

Max Phase: Preclinical

Molecular Formula: C16H25NO3

Molecular Weight: 279.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CCCC[C@@H]2N[C@@H](CO)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C16H25NO3/c1-11-6-8-12(9-7-11)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:  AOTIJLLHMOIGTB-VGWMRTNUSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    8.3411   -2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1156   -2.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6044   -3.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1298   -3.7680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3516   -3.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6502   -3.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3592   -1.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9364   -3.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2349   -3.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5211   -3.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6744   -2.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4215   -3.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8384   -3.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8197   -3.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1080   -3.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4071   -4.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4190   -4.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378   -5.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8358   -4.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7181   -5.2395    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
M  END

Alternative Forms

1. Parent:

   

   ALA3311515

   ---

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: 279.38

Molecular Weight (Monoisotopic): 279.1834

AlogP: 0.76

#Rotatable Bonds: 6

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: 9.63

CX LogP: 1.66

CX LogD: -0.53

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.58

Np Likeness Score: 1.22

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