N-4-methoxybenzyl-D-galactonoamidine

ID: ALA3359122

PubChem CID: 137007055

Max Phase: Preclinical

Molecular Formula: C14H20N2O5

Molecular Weight: 296.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C/N=C2\N[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C14H20N2O5/c1-21-9-4-2-8(3-5-9)6-15-14-13(20)12(19)11(18)10(7-17)16-14/h2-5,10-13,17-20H,6-7H2,1H3,(H,15,16)/t10-,11+,12+,13-/m1/s1

Standard InChI Key:  BUJSHVIRKFEOPO-MROQNXINSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   13.7808   -9.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7808  -10.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4861  -10.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1914  -10.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1914   -9.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4861   -8.9685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9003   -8.9747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8985  -10.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4861  -11.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0737  -10.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0719   -8.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0695   -8.1575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9027   -8.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6116   -7.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3214   -8.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0298   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0327   -6.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3212   -6.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6157   -6.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7403   -6.5335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4481   -6.9420    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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359122

   ---

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: 296.32

Molecular Weight (Monoisotopic): 296.1372

AlogP: -1.36

#Rotatable Bonds: 4

Polar Surface Area: 114.54

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.52

CX Basic pKa: 7.30

CX LogP: -1.56

CX LogD: -1.81

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.47

Np Likeness Score: 0.67

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