N-4-tert-butylbenzyl-D-galactonoamidine

ID: ALA3359666

PubChem CID: 137007057

Max Phase: Preclinical

Molecular Formula: C17H26N2O4

Molecular Weight: 322.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(C/N=C2\N[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C17H26N2O4/c1-17(2,3)11-6-4-10(5-7-11)8-18-16-15(23)14(22)13(21)12(9-20)19-16/h4-7,12-15,20-23H,8-9H2,1-3H3,(H,18,19)/t12-,13+,14+,15-/m1/s1

Standard InChI Key:  KYQDCEXEJARJQR-CBBWQLFWSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    6.7315  -10.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7315  -10.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4368  -11.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1421  -10.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1421  -10.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4368   -9.6453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8510   -9.6515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8492  -11.2849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4368  -12.0969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0244  -11.2849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0226   -9.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0202   -8.8343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8534   -8.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5623   -8.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2721   -8.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9805   -8.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9834   -7.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2719   -7.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5664   -7.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6910   -7.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3988   -7.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6909   -6.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3941   -6.7975    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
 17 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359666

   ---

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: 322.41

Molecular Weight (Monoisotopic): 322.1893

AlogP: -0.07

#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: 0.14

CX LogD: -0.11

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: 0.35

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