Hmdb loader

Showing metabocard for 3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose (HMDB0006700)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-30 13:19:15 UTC
Update Date2021-09-14 15:40:21 UTC
HMDB IDHMDB0006700
Secondary Accession Numbers
  • HMDB06700
Metabolite Identification
Common Name3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose
Description3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose is an oligosaccharide is a fucosylated oligosaccharide specific to human, and in milk forms part of the innate immune system. (PMID: 1579031 ). It is present in a number of proteins, such as human transferrin. Hepatocytes contain a receptor that binds glycoproteins specifically through the fucose in alpha13 linkage to N-acetylglucosamine. (PMID: 276862 ). It is also present in some forms of human kidney enzyme alpha-L-fucosidase (EC 3.2.1.51) (PMID: 7215135 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006700 (3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose)

  Mrv0541 02231220482D          

 25 25  0  0  1  0            999 V2000
   17.2303   -7.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5158   -6.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0868   -7.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0868   -9.0344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5158   -9.8594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9447   -7.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0394   -5.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1000   -6.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6053   -5.8602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3838   -3.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4783   -4.7395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8012   -7.7969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.8012   -8.6219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5158   -7.3844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5158   -9.0344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2303   -8.6219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2303   -6.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.9447   -6.5594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9480   -5.3716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9447   -9.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7572   -6.4161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2874   -7.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1356   -5.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1962   -3.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7265   -3.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 16  1  0  0  0  0
 14  2  1  6  0  0  0
 17  2  1  6  0  0  0
 12  3  1  6  0  0  0
 13  4  1  1  0  0  0
 15  5  1  1  0  0  0
 18  6  1  1  0  0  0
 21  7  1  6  0  0  0
  8 22  1  0  0  0  0
  9 23  2  0  0  0  0
 10 24  2  0  0  0  0
 19 11  1  6  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  1  1  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
Download

3D MOL for HMDB0006700 (3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose)

HMDB0006700
     RDKit          3D
3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose
 50 50  0  0  0  0  0  0  0  0999 V2000
    1.9314   -4.2105   -0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3216   -2.9118   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9713   -2.8907    0.9629 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505   -1.7195   -0.7625 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566   -0.4226   -0.1546 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3655    0.0558   -1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504   -0.7600   -1.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1665    0.4595    0.0193 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2039   -0.3409    0.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0421   -0.2808    0.1134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8360    0.4817    0.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137    0.6861    0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2013    1.5788   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267   -0.6162    0.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0582   -0.7456   -1.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -1.7410    0.6102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4293   -2.9970    0.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459   -1.5911   -0.2282 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9004   -2.7082    0.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5225    1.5734    1.0213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3022    2.2376    1.3547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4424    2.6239    0.5436 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5988    3.6215    1.5844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    3.3804   -0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473    4.0288   -0.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -4.1214   -1.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -4.6100   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8011   -4.8936   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178   -1.7410   -1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8622   -0.6161    0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143    1.0699   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7661    0.9141   -0.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811    0.3507   -0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939    1.1673    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2365    2.0342   -0.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.0533   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5092    2.4345   -0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8159   -0.6932    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9602   -0.4167   -1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598   -1.6369    1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -3.6086    0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847   -1.6670   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -2.9095    1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892    1.1488    1.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752    2.8691    2.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938    2.3398    0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889    3.2130    2.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7092    4.1898   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812    2.7583   -1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    4.5796    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  8 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 18 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  1
  6 31  1  0
  8 32  1  6
 10 33  1  6
 12 34  1  1
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  1
 15 39  1  0
 16 40  1  1
 17 41  1  0
 18 42  1  6
 19 43  1  0
 20 44  1  1
 21 45  1  0
 22 46  1  6
 23 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
M  END
Download

3D SDF for HMDB0006700 (3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose)

  Mrv0541 02231220482D          

 25 25  0  0  1  0            999 V2000
   17.2303   -7.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5158   -6.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0868   -7.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0868   -9.0344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5158   -9.8594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9447   -7.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0394   -5.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1000   -6.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6053   -5.8602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3838   -3.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4783   -4.7395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8012   -7.7969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.8012   -8.6219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5158   -7.3844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5158   -9.0344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2303   -8.6219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2303   -6.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.9447   -6.5594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9480   -5.3716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9447   -9.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7572   -6.4161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2874   -7.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1356   -5.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1962   -3.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7265   -3.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 16  1  0  0  0  0
 14  2  1  6  0  0  0
 17  2  1  6  0  0  0
 12  3  1  6  0  0  0
 13  4  1  1  0  0  0
 15  5  1  1  0  0  0
 18  6  1  1  0  0  0
 21  7  1  6  0  0  0
  8 22  1  0  0  0  0
  9 23  2  0  0  0  0
 10 24  2  0  0  0  0
 19 11  1  6  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  1  1  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006700

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O)[C@@H](O)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H25NO10/c1-5-9(20)11(22)12(23)14(24-5)25-13(10(21)8(19)4-17)7(3-16)15-6(2)18/h3,5,7-14,17,19-23H,4H2,1-2H3,(H,15,18)/t5-,7-,8+,9+,10+,11+,12-,13+,14-/m0/s1

> <INCHI_KEY>
YDWJUIXDZSJZHH-MYCHVAHWSA-N

> <FORMULA>
C14H25NO10

> <MOLECULAR_WEIGHT>
367.349

> <EXACT_MASS>
367.147846025

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
34.5530336085968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide

> <ALOGPS_LOGP>
-2.07

> <JCHEM_LOGP>
-4.580321435666667

> <ALOGPS_LOGS>
-0.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.233878335157096

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.419960500313563

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742017949320267

> <JCHEM_POLAR_SURFACE_AREA>
186.01

> <JCHEM_REFRACTIVITY>
79.3165

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0006700 (3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose)

HMDB0006700
     RDKit          3D
3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose
 50 50  0  0  0  0  0  0  0  0999 V2000
    1.9314   -4.2105   -0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3216   -2.9118   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9713   -2.8907    0.9629 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505   -1.7195   -0.7625 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566   -0.4226   -0.1546 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3655    0.0558   -1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504   -0.7600   -1.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1665    0.4595    0.0193 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2039   -0.3409    0.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0421   -0.2808    0.1134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8360    0.4817    0.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137    0.6861    0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2013    1.5788   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267   -0.6162    0.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0582   -0.7456   -1.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -1.7410    0.6102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4293   -2.9970    0.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459   -1.5911   -0.2282 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9004   -2.7082    0.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5225    1.5734    1.0213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3022    2.2376    1.3547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4424    2.6239    0.5436 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5988    3.6215    1.5844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    3.3804   -0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473    4.0288   -0.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -4.1214   -1.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -4.6100   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8011   -4.8936   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178   -1.7410   -1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8622   -0.6161    0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143    1.0699   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7661    0.9141   -0.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811    0.3507   -0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939    1.1673    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2365    2.0342   -0.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.0533   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5092    2.4345   -0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8159   -0.6932    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9602   -0.4167   -1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598   -1.6369    1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -3.6086    0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847   -1.6670   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -2.9095    1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892    1.1488    1.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752    2.8691    2.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938    2.3398    0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889    3.2130    2.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7092    4.1898   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812    2.7583   -1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    4.5796    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  8 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 18 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  1
  6 31  1  0
  8 32  1  6
 10 33  1  6
 12 34  1  1
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  1
 15 39  1  0
 16 40  1  1
 17 41  1  0
 18 42  1  6
 19 43  1  0
 20 44  1  1
 21 45  1  0
 22 46  1  6
 23 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
M  END
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PDB for HMDB0006700 (3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      32.163 -14.554   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.829 -12.244   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      28.162 -13.784   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      28.162 -16.864   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.829 -18.404   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      33.497 -13.784   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      35.540 -10.529   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      37.520 -12.889   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.130 -10.939   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      30.583  -7.133   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      32.626  -8.847   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      29.496 -14.554   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.496 -16.094   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.829 -13.784   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.829 -16.864   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.163 -16.094   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.163 -11.474   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.497 -12.244   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.636 -10.027   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.497 -16.864   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.013 -11.977   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.003 -13.156   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.120  -9.759   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      32.100  -7.400   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.089  -6.220   0.000  0.00  0.00           C+0
CONECT    1   14   16                                                       
CONECT    2   14   17                                                       
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   15                                                            
CONECT    6   18                                                            
CONECT    7   21                                                            
CONECT    8   22                                                            
CONECT    9   23                                                            
CONECT   10   24                                                            
CONECT   11   19   24                                                       
CONECT   12    3   13   14                                                  
CONECT   13    4   12   15                                                  
CONECT   14    1    2   12                                                  
CONECT   15    5   13   16                                                  
CONECT   16    1   15   20                                                  
CONECT   17    2   18   19                                                  
CONECT   18    6   17   21                                                  
CONECT   19   11   17   23                                                  
CONECT   20   16                                                            
CONECT   21    7   18   22                                                  
CONECT   22    8   21                                                       
CONECT   23    9   19                                                       
CONECT   24   10   11   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END
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3D PDB for HMDB0006700 (3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose)

COMPND    HMDB0006700
HETATM    1  C1  UNL     1       1.931  -4.211  -0.694  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.322  -2.912  -0.104  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.971  -2.891   0.963  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.950  -1.719  -0.762  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.357  -0.423  -0.155  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.366   0.056  -1.138  1.00  0.00           C  
HETATM    7  O2  UNL     1       4.050  -0.760  -1.723  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.166   0.459   0.019  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.204  -0.341   0.734  1.00  0.00           O  
HETATM   10  C6  UNL     1      -1.042  -0.281   0.113  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.836   0.482   0.976  1.00  0.00           O  
HETATM   12  C7  UNL     1      -3.114   0.686   0.489  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.201   1.579  -0.707  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.827  -0.616   0.181  1.00  0.00           C  
HETATM   15  O5  UNL     1      -4.058  -0.746  -1.186  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.928  -1.741   0.610  1.00  0.00           C  
HETATM   17  O6  UNL     1      -3.429  -2.997   0.332  1.00  0.00           O  
HETATM   18  C11 UNL     1      -1.646  -1.591  -0.228  1.00  0.00           C  
HETATM   19  O7  UNL     1      -0.900  -2.708   0.038  1.00  0.00           O  
HETATM   20  C12 UNL     1       1.523   1.573   1.021  1.00  0.00           C  
HETATM   21  O8  UNL     1       0.302   2.238   1.355  1.00  0.00           O  
HETATM   22  C13 UNL     1       2.442   2.624   0.544  1.00  0.00           C  
HETATM   23  O9  UNL     1       2.599   3.621   1.584  1.00  0.00           O  
HETATM   24  C14 UNL     1       1.958   3.380  -0.672  1.00  0.00           C  
HETATM   25  O10 UNL     1       0.747   4.029  -0.411  1.00  0.00           O  
HETATM   26  H1  UNL     1       1.700  -4.121  -1.786  1.00  0.00           H  
HETATM   27  H2  UNL     1       1.051  -4.610  -0.195  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.801  -4.894  -0.573  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.418  -1.741  -1.633  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.862  -0.616   0.788  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.514   1.070  -1.354  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.766   0.914  -0.858  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.981   0.351  -0.824  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.694   1.167   1.310  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.236   2.034  -0.699  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.143   1.053  -1.682  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.509   2.435  -0.680  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.816  -0.693   0.686  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.960  -0.417  -1.460  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.660  -1.637   1.686  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.656  -3.609   0.107  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.985  -1.667  -1.287  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.918  -2.909   1.012  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.889   1.149   1.970  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.575   2.869   2.094  1.00  0.00           H  
HETATM   46  H21 UNL     1       3.494   2.340   0.377  1.00  0.00           H  
HETATM   47  H22 UNL     1       3.089   3.213   2.318  1.00  0.00           H  
HETATM   48  H23 UNL     1       2.709   4.190  -0.867  1.00  0.00           H  
HETATM   49  H24 UNL     1       1.881   2.758  -1.561  1.00  0.00           H  
HETATM   50  H25 UNL     1       0.901   4.580   0.408  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3    4
CONECT    4    5   29
CONECT    5    6    8   30
CONECT    6    7    7   31
CONECT    8    9   20   32
CONECT    9   10
CONECT   10   11   18   33
CONECT   11   12
CONECT   12   13   14   34
CONECT   13   35   36   37
CONECT   14   15   16   38
CONECT   15   39
CONECT   16   17   18   40
CONECT   17   41
CONECT   18   19   42
CONECT   19   43
CONECT   20   21   22   44
CONECT   21   45
CONECT   22   23   24   46
CONECT   23   47
CONECT   24   25   48   49
CONECT   25   50
END
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SMILES for HMDB0006700 (3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose)

C[C@@H]1O[C@@H](O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O)[C@@H](O)[C@H](O)[C@@H]1O
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INCHI for HMDB0006700 (3-O-fucopyranosyl-2-acetamido-2-deoxyglucopyranose)

InChI=1S/C14H25NO10/c1-5-9(20)11(22)12(23)14(24-5)25-13(10(21)8(19)4-17)7(3-16)15-6(2)18/h3,5,7-14,17,19-23H,4H2,1-2H3,(H,15,18)/t5-,7-,8+,9+,10+,11+,12-,13+,14-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
-O-Fucopyranosyl-2-acetamido-2-deoxyglucopyranoseHMDB
2-(acetylamino)-2-Deoxy-3-O-(6-deoxy-alpha-L-galactopyranosyl)- D-glucoseHMDB
2-acetamido-2-Deoxy-3-O-alpha-L-fucopyranosyl-D-glucoseHMDB
2-acetamido-2-Deoxy-3-O-alpha-L-fucopyranosyl-delta-glucoseHMDB
Fuc-1-3-glcnacMeSH, HMDB
N-[(2R,3R,4R,5R)-4,5,6-Trihydroxy-1-oxo-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]ethanimidateGenerator, HMDB
3-O-Fucopyranosyl-2-acetamido-2-deoxyglucopyranoseMeSH
Chemical FormulaC14H25NO10
Average Molecular Weight367.349
Monoisotopic Molecular Weight367.147846025
IUPAC NameN-[(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide
Traditional NameN-[(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide
CAS Registry Number52630-68-9
SMILES
C[C@@H]1O[C@@H](O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C14H25NO10/c1-5-9(20)11(22)12(23)14(24-5)25-13(10(21)8(19)4-17)7(3-16)15-6(2)18/h3,5,7-14,17,19-23H,4H2,1-2H3,(H,15,18)/t5-,7-,8+,9+,10+,11+,12-,13+,14-/m0/s1
InChI KeyYDWJUIXDZSJZHH-MYCHVAHWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Amino saccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024032
KNApSAcK IDNot Available
Chemspider ID149653
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound171181
PDB IDNot Available
ChEBI ID168523
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAjisaka, Katsumi; Fujimoto, Hiroshi; Miyasato, Mariko. An a-L-fucosidase from Penicillium multicolor as a candidate enzyme for the synthesis of a (1®3)-linked fucosyl oligosaccharides by transglycosylation. Carbohydrate Research (1998), 309(1), 125-129.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Perret S, Sabin C, Dumon C, Pokorna M, Gautier C, Galanina O, Ilia S, Bovin N, Nicaise M, Desmadril M, Gilboa-Garber N, Wimmerova M, Mitchell EP, Imberty A: Structural basis for the interaction between human milk oligosaccharides and the bacterial lectin PA-IIL of Pseudomonas aeruginosa. Biochem J. 2005 Jul 15;389(Pt 2):325-32. [PubMed:15790314 ]
  2. Prieels JP, Pizzo SV, Glasgow LR, Paulson JC, Hill RL: Hepatic receptor that specifically binds oligosaccharides containing fucosyl alpha1 leads to 3 N-acetylglucosamine linkages. Proc Natl Acad Sci U S A. 1978 May;75(5):2215-9. [PubMed:276862 ]
  3. Bakh NL, Beier EM, Bovin NV, Zurabian SE, Vidershain GIa: [Specificity and properties of multiple forms of human alpha-L-fucosidase]. Dokl Akad Nauk SSSR. 1980;255(4):996-9. [PubMed:7215135 ]
  4. Bachner M, Alain T: [Future of psychiatry--a medical specialty or an interdisciplinary activity?]. Lakartidningen. 1992 May 6;89(19):1652-3; discussion 1653-4. [PubMed:1579031 ]