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

ID: ALA496420

PubChem CID: 44583545

Max Phase: Preclinical

Molecular Formula: C12H21NO10

Molecular Weight: 339.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=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/C12H21NO10/c1-21-11(20)13-7-5(15)3-12(22-2,10(18)19)23-9(7)8(17)6(16)4-14/h5-9,14-17H,3-4H2,1-2H3,(H,13,20)(H,18,19)/t5-,6+,7+,8+,9+,12-/m0/s1

Standard InChI Key:  XDHVEPKMCUIGCM-WHIYQGQESA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    4.9993  -14.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7211  -14.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4321  -14.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4276  -13.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7058  -12.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885  -13.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9840  -12.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4136  -12.4521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670  -11.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2749  -12.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1493  -14.5213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7278  -15.3569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4455  -15.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4523  -16.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1566  -15.3452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2892  -14.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792  -13.7205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5705  -14.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980  -15.3680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618  -13.3133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604  -14.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416  -14.1533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1345  -12.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1701  -16.9952    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:

   

   ALA496420

   (2S,4S,5R,6R)-4-hydroxy-2-methoxy-5-(methoxycarbonylamino)-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: 339.30

Molecular Weight (Monoisotopic): 339.1165

AlogP: -3.00

#Rotatable Bonds: 6

Polar Surface Area: 175.01

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.99

CX Basic pKa: ┄

CX LogP: -2.30

CX LogD: -5.78

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: 1.23

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