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

ID: ALA496419

PubChem CID: 44583544

Max Phase: Preclinical

Molecular Formula: C17H23NO9

Molecular Weight: 385.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@]1(C(=O)O)C[C@H](O)[C@@H](NC(=O)c2ccccc2)[C@H]([C@H](O)[C@H](O)CO)O1

Standard InChI:  InChI=1S/C17H23NO9/c1-26-17(16(24)25)7-10(20)12(14(27-17)13(22)11(21)8-19)18-15(23)9-5-3-2-4-6-9/h2-6,10-14,19-22H,7-8H2,1H3,(H,18,23)(H,24,25)/t10-,11+,12+,13+,14+,17-/m0/s1

Standard InChI Key:  LYUOFMADPSVYQI-UJNKEFAKSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -2.1048  -14.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3830  -14.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6719  -14.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763  -13.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3981  -12.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155  -13.2602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200  -12.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903  -12.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370  -11.6169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292  -12.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454  -14.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3761  -15.3214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584  -15.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517  -16.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527  -15.3097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8149  -14.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8249  -13.6847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5336  -14.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8062  -15.3325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5424  -13.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2438  -14.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9626  -14.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0307  -12.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631  -16.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3567  -17.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382  -18.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751  -17.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652  -16.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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  2  0
  2 12  1  1
 24 25  1  0
  5  6  1  0
 25 26  2  0
 12 13  1  0
 26 27  1  0
 27 28  2  0
 28 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA496419

   BzNH(-5d)b-Kdn2Me

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: 385.37

Molecular Weight (Monoisotopic): 385.1373

AlogP: -1.92

#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: 2.90

CX Basic pKa: ┄

CX LogP: -1.07

CX LogD: -4.55

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.31

Np Likeness Score: 0.79

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