6-Acetamido-6-deoxy-castanospermine

ID: ALA1232979

Cas Number: 134100-29-1

PubChem CID: 9837515

Max Phase: Preclinical

Molecular Formula: C10H18N2O4

Molecular Weight: 230.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1CN2CC[C@H](O)[C@@H]2[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C10H18N2O4/c1-5(13)11-6-4-12-3-2-7(14)8(12)10(16)9(6)15/h6-10,14-16H,2-4H2,1H3,(H,11,13)/t6-,7-,8+,9+,10+/m0/s1

Standard InChI Key:  IHKWXDCSAKJQKM-SRQGCSHVSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    2.1267    1.8678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    1.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6977    1.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    0.6303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6977    0.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6977   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122   -1.0197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -1.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -1.8447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168    0.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312    0.2178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159    0.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0008   -0.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -0.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708   -1.6467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358   -1.6017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  2  4  1  0
  5  4  1  6
  5  6  1  0
 10  5  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  6
  8 12  1  0
 10 11  1  0
 12 11  1  0
 13 11  1  0
 12 15  1  0
 14 13  1  0
 15 14  1  0
 15 16  1  1
 12 17  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1232979

   6-Acetamido-6-Deoxy-Castanospermine

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: 230.26

Molecular Weight (Monoisotopic): 230.1267

AlogP: -2.34

#Rotatable Bonds: 1

Polar Surface Area: 93.03

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: 8.30

CX LogP: -2.84

CX LogD: -3.80

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.41

Np Likeness Score: 1.23

References

1. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

2. Boyd RE, Lee G, Rybczynski P, Benjamin ER, Khanna R, Wustman BA, Valenzano KJ..  (2013)  Pharmacological chaperones as therapeutics for lysosomal storage diseases.,  56  (7): [PMID:23363020] [10.1021/jm301557k]

3. Karhu E, Isojärvi J, Vuorela P, Hanski L, Fallarero A..  (2017)  Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy.,  80  (10): [PMID:29043803] [10.1021/acs.jnatprod.6b01052]

4.  (2016)  Compositions and methods relating to inhibiting serine hyrdoxymethyltransferase 2 activity, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data