2-fluoro-N-benzyl-D-galactonoamidine

ID: ALA3359667

PubChem CID: 136078852

Max Phase: Preclinical

Molecular Formula: C13H17FN2O4

Molecular Weight: 284.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1N/C(=N\Cc2ccccc2F)[C@H](O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C13H17FN2O4/c14-8-4-2-1-3-7(8)5-15-13-12(20)11(19)10(18)9(6-17)16-13/h1-4,9-12,17-20H,5-6H2,(H,15,16)/t9-,10+,11+,12-/m1/s1

Standard InChI Key:  KBVBVWYAKQVNNW-NOOOWODRSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   25.5723   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5723   -4.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2776   -4.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9829   -4.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9829   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2776   -2.9716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6918   -2.9778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6900   -4.6111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2776   -5.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8652   -4.6111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8634   -2.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8610   -2.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6942   -2.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4031   -1.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1129   -2.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8213   -1.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8242   -0.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1127   -0.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4072   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1092   -2.9865    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  4  8  1  6
  3  9  1  1
  2 10  1  1
  1 11  1  1
 11 12  1  0
  7 13  1  0
 13 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
 15 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359667

   ---

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: 284.29

Molecular Weight (Monoisotopic): 284.1172

AlogP: -1.23

#Rotatable Bonds: 3

Polar Surface Area: 105.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.52

CX Basic pKa: 7.23

CX LogP: -1.26

CX LogD: -1.48

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.48

Np Likeness Score: 0.24

References

1. Fan QH, Claunch KA, Striegler S..  (2014)  Structure-activity relationship of highly potent galactonoamidine inhibitors toward β-galactosidase (Aspergillus oryzae).,  57  (21): [PMID:25295392] [10.1021/jm501111y]

2. Pickens JB, Striegler S, Fan QH..  (2016)  Arabinoamidine synthesis and its inhibition toward β-glucosidase (sweet almonds) in comparison to a library of galactonoamidines.,  24  (16): [PMID:27298003] [10.1016/j.bmc.2016.04.069]

3. Pickens JB, Wang F, Striegler S..  (2017)  Picomolar inhibition of β-galactosidase (bovine liver) attributed to loop closure.,  25  (20): [PMID:28844803] [10.1016/j.bmc.2017.07.020]

Source

Source(1):

• Scientific Literature