D-galactono-gama-lactam

ID: ALA3359684

PubChem CID: 12883628

Max Phase: Preclinical

Molecular Formula: C6H11NO5

Molecular Weight: 177.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C6H11NO5/c8-1-2-3(9)4(10)5(11)6(12)7-2/h2-5,8-11H,1H2,(H,7,12)/t2-,3+,4+,5-/m1/s1

Standard InChI Key:  AJJXPYDGVXIEHE-MGCNEYSASA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
   13.7808  -22.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7808  -23.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4861  -23.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1914  -23.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1914  -22.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4861  -21.8661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9003  -21.8723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8985  -23.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4861  -24.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0737  -23.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0719  -21.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0695  -21.0551    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA3359684

   (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one

Molecule Features

Natural Product: Yes

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: 177.16

Molecular Weight (Monoisotopic): 177.0637

AlogP: -3.44

#Rotatable Bonds: 1

Polar Surface Area: 110.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.99

CX Basic pKa: ┄

CX LogP: -3.47

CX LogD: -3.47

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.29

Np Likeness Score: 1.84

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