O-Methyl-5-N-propaonyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic Acid

ID: ALA444218

PubChem CID: 44583526

Max Phase: Preclinical

Molecular Formula: C13H23NO9

Molecular Weight: 337.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)O[C@](OC)(C(=O)O)C[C@@H]1O

Standard InChI:  InChI=1S/C13H23NO9/c1-3-8(18)14-9-6(16)4-13(22-2,12(20)21)23-11(9)10(19)7(17)5-15/h6-7,9-11,15-17,19H,3-5H2,1-2H3,(H,14,18)(H,20,21)/t6-,7+,9+,10+,11+,13-/m0/s1

Standard InChI Key:  DVLSRKZXZWERIP-FWADUHFYSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   12.2773    0.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9991    0.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7102    0.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7058    1.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9840    2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2667    1.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2622    2.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6918    2.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2451    3.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5530    1.9740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4274    0.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0060   -0.4800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7237   -0.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7304   -1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4347   -0.4684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5673    0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5573    1.1564    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8486    0.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5760   -0.4911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8398    1.5636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1385    0.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4198    0.7236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4127    2.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4482   -2.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  1
  5  6  1  0
 12 13  1  0
 13 14  1  0
  5  7  1  0
 13 15  2  0
  1  2  1  0
  1 16  1  0
  5  8  1  1
  1 17  1  1
  1  6  1  0
 16 18  1  0
  2  3  1  0
 16 19  1  6
  7  9  1  0
 18 20  1  1
  7 10  2  0
 18 21  1  0
  3  4  1  0
 21 22  1  0
  3 11  1  6
  8 23  1  0
  4  5  1  0
 14 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA444218

   (2S,4S,5R,6R)-4-hydroxy-2-methoxy-5-(propanoylamino)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

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: 337.33

Molecular Weight (Monoisotopic): 337.1373

AlogP: -2.83

#Rotatable Bonds: 7

Polar Surface Area: 165.78

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.13

CX Basic pKa: ┄

CX LogP: -2.22

CX LogD: -5.68

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: 1.12

References

1. Johansson S, Nilsson E, Qian W, Guilligay D, Crepin T, Cusack S, Arnberg N, Elofsson M..  (2009)  Design, synthesis, and evaluation of N-acyl modified sialic acids as inhibitors of adenoviruses causing epidemic keratoconjunctivitis.,  52  (12): [PMID:19456100] [10.1021/jm801609s]

Source

Source(1):

• Scientific Literature