O-Methyl-5-N-(3-methylureido)-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic Acid

ID: ALA496223

PubChem CID: 44583546

Max Phase: Preclinical

Molecular Formula: C12H22N2O9

Molecular Weight: 338.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=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/C12H22N2O9/c1-13-11(21)14-7-5(16)3-12(22-2,10(19)20)23-9(7)8(18)6(17)4-15/h5-9,15-18H,3-4H2,1-2H3,(H,19,20)(H2,13,14,21)/t5-,6+,7+,8+,9+,12-/m0/s1

Standard InChI Key:  RDQWITGUKDOLBI-WHIYQGQESA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   13.0336  -14.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7554  -14.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4664  -14.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4620  -13.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7402  -13.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0229  -13.5710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0184  -12.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4480  -12.7272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0013  -11.9278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3092  -13.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1837  -14.7964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7622  -15.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4799  -16.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4866  -16.8636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1909  -15.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3235  -14.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3135  -13.9956    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6048  -14.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3322  -15.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5960  -13.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8947  -14.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1760  -14.4284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1689  -13.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2045  -17.2703    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:

   

   ALA496223

   (2S,4S,5R,6R)-4-hydroxy-2-methoxy-5-(methylcarbamoylamino)-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: 338.31

Molecular Weight (Monoisotopic): 338.1325

AlogP: -3.42

#Rotatable Bonds: 6

Polar Surface Area: 177.81

Molecular Species: ACID

HBA: 8

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.09

CX Basic pKa: ┄

CX LogP: -3.03

CX LogD: -6.49

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.26

Np Likeness Score: 1.08

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