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

ID: ALA497016

PubChem CID: 44583528

Max Phase: Preclinical

Molecular Formula: C14H25NO9

Molecular Weight: 351.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@]1(C(=O)O)C[C@H](O)[C@@H](NC(=O)C(C)C)[C@H]([C@H](O)[C@H](O)CO)O1

Standard InChI:  InChI=1S/C14H25NO9/c1-6(2)12(20)15-9-7(17)4-14(23-3,13(21)22)24-11(9)10(19)8(18)5-16/h6-11,16-19H,4-5H2,1-3H3,(H,15,20)(H,21,22)/t7-,8+,9+,10+,11+,14-/m0/s1

Standard InChI Key:  ZXJDQYKVGOJZAM-DYGUYAMTSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    5.3981   -6.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1199   -7.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8310   -6.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8264   -5.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046   -5.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3874   -5.8026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3828   -4.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125   -4.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3658   -4.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6737   -5.4096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5481   -7.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1266   -7.8636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8444   -8.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8512   -9.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5555   -7.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6880   -7.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6780   -6.2272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9693   -6.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6968   -7.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9606   -5.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -7.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5404   -6.6600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5334   -5.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5689   -9.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1402   -9.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  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
  2 12  1  1
 14 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA497016

   (2S,4S,5R,6R)-4-hydroxy-2-methoxy-5-(2-methylpropanoylamino)-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: 351.35

Molecular Weight (Monoisotopic): 351.1529

AlogP: -2.58

#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: 3.19

CX Basic pKa: ┄

CX LogP: -1.68

CX LogD: -5.12

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.29

Np Likeness Score: 1.19

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