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

ID: ALA522057

PubChem CID: 44583547

Max Phase: Preclinical

Molecular Formula: C15H27NO10

Molecular Weight: 381.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H27NO10/c1-14(2,3)26-13(23)16-9-7(18)5-15(24-4,12(21)22)25-11(9)10(20)8(19)6-17/h7-11,17-20H,5-6H2,1-4H3,(H,16,23)(H,21,22)/t7-,8+,9+,10+,11+,15-/m0/s1

Standard InChI Key:  VNVNHTKPFLFVHN-AVRHJQNXSA-N

Molfile:  

     RDKit          2D

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   -0.0399  -23.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6711  -23.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666  -22.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0552  -22.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725  -22.4623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770  -21.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526  -21.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7941  -20.8192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862  -22.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3883  -23.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0332  -24.5235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6845  -24.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913  -25.7550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956  -24.5117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719  -23.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4819  -22.8869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1906  -23.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631  -24.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1993  -22.4797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9006  -23.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194  -23.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735  -22.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0197  -26.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379  -26.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3919  -26.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320  -25.4588    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
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  1 16  1  0
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  1 17  1  1
  1  6  1  0
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 16 19  1  6
  7  9  1  0
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  7 10  2  0
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 21 22  1  0
  3 11  1  6
  8 23  1  0
  4  5  1  0
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  2 12  1  1
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  5  6  1  0
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 12 13  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA522057

   (2S,4S,5R,6R)-4-hydroxy-2-methoxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-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: 381.38

Molecular Weight (Monoisotopic): 381.1635

AlogP: -1.83

#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: 2.78

CX Basic pKa: ┄

CX LogP: -1.25

CX LogD: -4.74

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.31

Np Likeness Score: 0.90

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