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

ID: ALA497015

PubChem CID: 44583527

Max Phase: Preclinical

Molecular Formula: C14H25NO9

Molecular Weight: 351.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=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/C14H25NO9/c1-3-4-9(19)15-10-7(17)5-14(23-2,13(21)22)24-12(10)11(20)8(18)6-16/h7-8,10-12,16-18,20H,3-6H2,1-2H3,(H,15,19)(H,21,22)/t7-,8+,10+,11+,12+,14-/m0/s1

Standard InChI Key:  ZOLHANKVXPTAEF-KLKPRGAGSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.1504   -6.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -7.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7176   -6.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7221   -5.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -5.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1612   -5.8391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1657   -5.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7361   -4.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827   -4.1960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -5.4461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -7.0646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4219   -7.9002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7042   -8.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -9.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -7.8884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8605   -7.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8706   -6.2637    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5793   -6.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517   -7.9113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879   -5.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2893   -7.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0081   -6.6965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152   -5.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0203   -9.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272  -10.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  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
  2 12  1  1
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA497015

   (2S,4S,5R,6R)-5-(butanoylamino)-4-hydroxy-2-methoxy-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: 351.35

Molecular Weight (Monoisotopic): 351.1529

AlogP: -2.44

#Rotatable Bonds: 8

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: -1.78

CX LogD: -5.24

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.28

Np Likeness Score: 1.03

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