N-cycloheptylmethyl-D-galactonoamidine

ID: ALA3359682

PubChem CID: 137007064

Max Phase: Preclinical

Molecular Formula: C14H26N2O4

Molecular Weight: 286.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1N/C(=N\CC2CCCCCC2)[C@H](O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H26N2O4/c17-8-10-11(18)12(19)13(20)14(16-10)15-7-9-5-3-1-2-4-6-9/h9-13,17-20H,1-8H2,(H,15,16)/t10-,11+,12+,13-/m1/s1

Standard InChI Key:  CMGWVGRBQOBCHY-MROQNXINSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    1.1267  -22.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1267  -23.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320  -24.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373  -23.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373  -22.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320  -22.5512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2462  -22.5574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2444  -24.1907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320  -25.0028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4196  -24.1907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178  -22.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154  -21.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486  -21.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9575  -21.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8997  -20.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005  -19.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331  -21.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3077  -20.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4154  -21.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128  -20.7899    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
 14 15  1  0
 15 16  1  0
 14 17  1  0
 16 18  1  0
 17 19  1  0
 18 20  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359682

   ---

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: 286.37

Molecular Weight (Monoisotopic): 286.1893

AlogP: -0.60

#Rotatable Bonds: 3

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: 7.90

CX LogP: -0.57

CX LogD: -1.18

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.45

Np Likeness Score: 0.99

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