N-benzyl-D-galactonoamidine

ID: ALA3359669

PubChem CID: 136777105

Max Phase: Preclinical

Molecular Formula: C13H18N2O4

Molecular Weight: 266.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1N/C(=N\Cc2ccccc2)[C@H](O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C13H18N2O4/c16-7-9-10(17)11(18)12(19)13(15-9)14-6-8-4-2-1-3-5-8/h1-5,9-12,16-19H,6-7H2,(H,14,15)/t9-,10+,11+,12-/m1/s1

Standard InChI Key:  BQHXLVRLDGOOJK-NOOOWODRSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    1.3579   -3.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579   -4.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0631   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7684   -4.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7684   -3.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0631   -2.9840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4773   -2.9902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4755   -4.6235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0631   -5.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507   -4.6235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6490   -2.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4797   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886   -1.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8985   -2.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6069   -1.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6097   -0.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8982   -0.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1927   -0.9555    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA3359669

   ---

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: 266.30

Molecular Weight (Monoisotopic): 266.1267

AlogP: -1.37

#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: 7.30

CX LogP: -1.40

CX LogD: -1.65

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.46

Np Likeness Score: 0.74

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