N-n-dodecyl-D-galactonoamidine

ID: ALA3359675

PubChem CID: 137007060

Max Phase: Preclinical

Molecular Formula: C18H36N2O4

Molecular Weight: 344.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC/N=C1\N[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C18H36N2O4/c1-2-3-4-5-6-7-8-9-10-11-12-19-18-17(24)16(23)15(22)14(13-21)20-18/h14-17,21-24H,2-13H2,1H3,(H,19,20)/t14-,15+,16+,17-/m1/s1

Standard InChI Key:  OZZTYUDTMQTEKD-LTIDMASMSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    1.8573  -17.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573  -17.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625  -18.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2678  -17.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2678  -17.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625  -16.7070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767  -16.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9749  -18.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625  -19.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501  -18.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1484  -16.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460  -15.8960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9791  -15.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6880  -15.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6921  -14.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865  -14.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906  -13.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2850  -13.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891  -12.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5835  -11.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737  -12.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8696  -13.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598  -13.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557  -14.2520    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
 15 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359675

   ---

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: 344.50

Molecular Weight (Monoisotopic): 344.2675

AlogP: 1.35

#Rotatable Bonds: 12

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: 7.97

CX LogP: 1.75

CX LogD: 1.09

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.34

Np Likeness Score: 0.88

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]

Source

Source(1):

• Scientific Literature