D-galactonoamidine

ID: ALA3359683

PubChem CID: 9989749

Max Phase: Preclinical

Molecular Formula: C6H12N2O4

Molecular Weight: 176.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C1N[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C6H12N2O4/c7-6-5(12)4(11)3(10)2(1-9)8-6/h2-5,9-12H,1H2,(H2,7,8)/t2-,3+,4+,5-/m1/s1

Standard InChI Key:  KIFBXZRNIGNERW-MGCNEYSASA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
    8.1513  -22.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1513  -23.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8566  -23.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5618  -23.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5618  -22.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8566  -21.8372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2707  -21.8434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2689  -23.4767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8566  -24.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4442  -23.4767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4424  -21.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4400  -21.0262    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA3359683

   (2R,3S,4S,5S)-6-amino-2-(hydroxymethyl)-2,3,4,5-tetrahydropyridine-3,4,5-triol

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: 176.17

Molecular Weight (Monoisotopic): 176.0797

AlogP: -2.99

#Rotatable Bonds: 1

Polar Surface Area: 116.80

Molecular Species: BASE

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.52

CX Basic pKa: 9.03

CX LogP: -3.35

CX LogD: -4.93

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.25

Np Likeness Score: 1.65

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