N-(2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide

ID: ALA469447

Cas Number: 14215-68-0

PubChem CID: 35717

Product Number: A111905, Order Now?

Max Phase: Preclinical

Molecular Formula: C8H15NO6

Molecular Weight: 221.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8?/m1/s1

Standard InChI Key:  OVRNDRQMDRJTHS-KEWYIRBNSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -3.6047    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6047    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4662    1.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3214    1.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    2.6776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196    0.2022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680    0.2022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4692   -0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7543   -1.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1852   -1.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  8  1  1
  1  6  1  0
  8  9  1  0
  2  3  1  0
  2 10  1  1
  3  4  1  0
  3 11  1  1
  4  5  1  0
  4 12  1  6
  5  6  1  0
 12 13  1  0
 13 14  1  0
  5  7  1  0
 13 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA469447

   N-Acetyl-D-galactosamine

Molecule Features

Natural Product: Yes

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: 221.21

Molecular Weight (Monoisotopic): 221.0899

AlogP: -3.08

#Rotatable Bonds: 2

Polar Surface Area: 119.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.60

CX Basic pKa: ┄

CX LogP: -3.22

CX LogD: -3.22

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.34

Np Likeness Score: 2.02

References

1. Dumas DP, Ichikawa Y, Wong C, Lowe JB, Nair RP.  (1991)  Enzymatic synthesis of sialyl Lex and derivatives based on a recombinant fucosyltransferase,  1  (8): [10.1016/S0960-894X(00)80270-X]

2. Bhat N, Joe A, PereiraPerrin M, Ward HD..  (2007)  Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro.,  282  (48): [PMID:17905738] [10.1074/jbc.m706950200]

3. Stokmaier D, Khorev O, Cutting B, Born R, Ricklin D, Ernst TO, Böni F, Schwingruber K, Gentner M, Wittwer M, Spreafico M, Vedani A, Rabbani S, Schwardt O, Ernst B..  (2009)  Design, synthesis and evaluation of monovalent ligands for the asialoglycoprotein receptor (ASGP-R).,  17  (20): [PMID:19762243] [10.1016/j.bmc.2009.08.049]

4.  (2014)  Fibcd1 for the prevention and treatment of diseases, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data