N-3-phenylpropyl-D-galactonoamidine

ID: ALA3359677

PubChem CID: 137007061

Max Phase: Preclinical

Molecular Formula: C15H22N2O4

Molecular Weight: 294.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1N/C(=N\CCCc2ccccc2)[C@H](O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H22N2O4/c18-9-11-12(19)13(20)14(21)15(17-11)16-8-4-7-10-5-2-1-3-6-10/h1-3,5-6,11-14,18-21H,4,7-9H2,(H,16,17)/t11-,12+,13+,14-/m1/s1

Standard InChI Key:  IBWPCRZCROGJCY-ZOBORPQBSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   11.2797  -16.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2797  -17.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9850  -17.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6903  -17.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6903  -16.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9850  -16.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3992  -16.1395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3974  -17.7729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9850  -18.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5726  -17.7729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5708  -16.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5684  -15.3224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4016  -15.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1105  -14.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1146  -14.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4090  -13.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4154  -12.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7106  -12.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9999  -12.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9984  -13.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7037  -14.0998    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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359677

   ---

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: 294.35

Molecular Weight (Monoisotopic): 294.1580

AlogP: -0.94

#Rotatable Bonds: 5

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: 7.96

CX LogP: -0.67

CX LogD: -1.33

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.45

Np Likeness Score: 0.82

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