N-cyclohexyl-D-galactonoamidine

ID: ALA3359679

PubChem CID: 118723765

Max Phase: Preclinical

Molecular Formula: C12H22N2O4

Molecular Weight: 258.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1N/C(=N\C2CCCCC2)[C@H](O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H22N2O4/c15-6-8-9(16)10(17)11(18)12(14-8)13-7-4-2-1-3-5-7/h7-11,15-18H,1-6H2,(H,13,14)/t8-,9+,10+,11-/m1/s1

Standard InChI Key:  LIPYOJRMSNSLPB-VPOLOUISSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   20.7146  -15.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7146  -16.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4198  -16.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1251  -16.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1251  -15.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4198  -15.3203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8340  -15.3265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8322  -16.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4198  -17.7718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0074  -16.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0057  -15.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0033  -14.5093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8364  -14.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5454  -14.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5497  -13.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8450  -12.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1343  -13.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1283  -14.1025    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
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359679

   ---

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: 258.32

Molecular Weight (Monoisotopic): 258.1580

AlogP: -1.24

#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: -1.33

CX LogD: -1.76

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.43

Np Likeness Score: 1.01

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