N-n-heptyl-D-galactonoamidine

ID: ALA3359674

PubChem CID: 137007059

Max Phase: Preclinical

Molecular Formula: C13H26N2O4

Molecular Weight: 274.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H26N2O4/c1-2-3-4-5-6-7-14-13-12(19)11(18)10(17)9(8-16)15-13/h9-12,16-19H,2-8H2,1H3,(H,14,15)/t9-,10+,11+,12-/m1/s1

Standard InChI Key:  XOEPKXNFJYTFLJ-NOOOWODRSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   33.9465  -10.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9465  -11.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6517  -11.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3570  -11.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3570  -10.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6517  -10.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0659  -10.0354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0641  -11.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6517  -12.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2393  -11.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2376  -10.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2352   -9.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0683   -9.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7772   -8.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7813   -8.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0757   -7.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0798   -6.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3742   -6.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3783   -5.5419    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
M  END

Alternative Forms

1. Parent:

   

   ALA3359674

   ---

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: 274.36

Molecular Weight (Monoisotopic): 274.1893

AlogP: -0.60

#Rotatable Bonds: 7

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: -0.47

CX LogD: -1.13

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.40

Np Likeness Score: 1.11

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