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

ID: ALA524074

PubChem CID: 44583529

Max Phase: Preclinical

Molecular Formula: C15H27NO9

Molecular Weight: 365.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC(=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/C15H27NO9/c1-3-4-5-10(20)16-11-8(18)6-15(24-2,14(22)23)25-13(11)12(21)9(19)7-17/h8-9,11-13,17-19,21H,3-7H2,1-2H3,(H,16,20)(H,22,23)/t8-,9+,11+,12+,13+,15-/m0/s1

Standard InChI Key:  CIRHSRRVTGMXJP-BTIXGSHYSA-N

Molfile:  

     RDKit          2D

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   13.4968   -6.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2187   -6.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9297   -6.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9252   -5.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2034   -4.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4861   -5.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4816   -4.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9112   -4.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4645   -3.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7724   -4.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6469   -6.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2254   -7.2450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9431   -7.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9499   -8.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6543   -7.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7867   -6.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7767   -5.6085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0680   -6.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7955   -7.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0593   -5.2013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3579   -6.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6391   -6.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6321   -4.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6677   -8.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6745   -9.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3922  -10.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 24 25  1  0
  5  6  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA524074

   (2S,4S,5R,6R)-4-hydroxy-2-methoxy-5-(pentanoylamino)-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: 365.38

Molecular Weight (Monoisotopic): 365.1686

AlogP: -2.05

#Rotatable Bonds: 9

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: 3.05

CX Basic pKa: ┄

CX LogP: -1.33

CX LogD: -4.80

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.27

Np Likeness Score: 1.02

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