6-azido-6-deoxytrehalose

ID: ALA1632045

PubChem CID: 9951096

Max Phase: Preclinical

Molecular Formula: C12H21N3O10

Molecular Weight: 367.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=NC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H21N3O10/c13-15-14-1-3-5(17)7(19)9(21)11(23-3)25-12-10(22)8(20)6(18)4(2-16)24-12/h3-12,16-22H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1

Standard InChI Key:  PYYKZQALXCDCIW-LIZSDCNHSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -1.8128   -6.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8128   -7.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020   -7.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870   -7.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870   -6.4698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020   -6.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3267   -7.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020   -5.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -4.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3298   -5.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0411   -4.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0476   -3.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291   -3.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -3.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -5.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527   -6.0624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918   -5.6336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4672   -6.4741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1818   -6.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -8.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020   -8.5305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5306   -7.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -6.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644   -3.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -2.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058   -3.5766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  6
  6  8  1  0
  9  8  1  6
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  1
 15 16  1  0
  6 17  1  6
 16 18  2  0
 18 19  2  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
  1 23  1  1
  3 21  1  1
 12 24  1  6
  7 20  1  0
 13 25  1  1
  2 22  1  6
 14 26  1  6
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1632045

   6-Azido-6-deoxy-alpha,alpha-D-trehalose

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: 367.31

Molecular Weight (Monoisotopic): 367.1227

AlogP: -4.08

#Rotatable Bonds: 5

Polar Surface Area: 218.06

Molecular Species: ACID

HBA: 11

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -10.23

CX Basic pKa: ┄

CX LogP: -3.88

CX LogD: -4.00

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.14

Np Likeness Score: 1.59

References

1. Scheich C, Puetter V, Schade M..  (2010)  Novel small molecule inhibitors of MDR Mycobacterium tuberculosis by NMR fragment screening of antigen 85C.,  53  (23): [PMID:21073150] [10.1021/jm100993z]

2. Thanna S, Sucheck SJ..  (2016)  Targeting the trehalose utilization pathways of Mycobacterium tuberculosis.,  7  (1): [PMID:26941930] [10.1039/c5md00376h]

3. Singh K, Kulkarni SS..  (2022)  Small Carbohydrate Derivatives as Potent Antibiofilm Agents.,  65  (13.0): [PMID:35777073] [10.1021/acs.jmedchem.1c01039]

Source

Source(1):

• Scientific Literature