3-methyl-Nbenzyl-D-galactonoamidine

ID: ALA3359671

PubChem CID: 136078850

Max Phase: Preclinical

Molecular Formula: C14H20N2O4

Molecular Weight: 280.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C/N=C2\N[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)c1

Standard InChI:  InChI=1S/C14H20N2O4/c1-8-3-2-4-9(5-8)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:  YCCNZNZQZKBAOG-MROQNXINSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   13.2401   -3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2401   -4.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9454   -5.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6507   -4.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6507   -3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9454   -3.3926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3596   -3.3988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3578   -5.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9454   -5.8442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5330   -5.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5312   -3.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5289   -2.5816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3620   -2.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0709   -2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7808   -2.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4892   -2.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4920   -1.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7805   -0.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0750   -1.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7800   -0.1420    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
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359671

   ---

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: 280.32

Molecular Weight (Monoisotopic): 280.1423

AlogP: -1.06

#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: 7.30

CX LogP: -0.89

CX LogD: -1.14

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.49

Np Likeness Score: 0.42

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