N-cyclopropyl-D-galactonoamidine

ID: ALA3359678

PubChem CID: 118723764

Max Phase: Preclinical

Molecular Formula: C9H16N2O4

Molecular Weight: 216.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1N/C(=N\C2CC2)[C@H](O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C9H16N2O4/c12-3-5-6(13)7(14)8(15)9(11-5)10-4-1-2-4/h4-8,12-15H,1-3H2,(H,10,11)/t5-,6+,7+,8-/m1/s1

Standard InChI Key:  SPASZKJKXKMWJL-VGRMVHKJSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
   15.9765  -15.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9765  -16.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6818  -17.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3871  -16.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3871  -15.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6818  -15.4606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0960  -15.4668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0942  -17.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6818  -17.9122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2694  -17.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2676  -15.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2652  -14.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0984  -14.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5068  -13.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6896  -13.9400    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
 14 13  1  0
 15 14  1  0
 13 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359678

   ---

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: 216.24

Molecular Weight (Monoisotopic): 216.1110

AlogP: -2.41

#Rotatable Bonds: 2

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: 7.64

CX LogP: -2.66

CX LogD: -3.09

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.35

Np Likeness Score: 1.29

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