MiMeDB: Showing metabocard for Aspartylglycosamine (MMDBc0000350)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:35:54 UTC

Update Date

2024-04-30 19:31:54 UTC

Metabolite ID

MMDBc0000350

Metabolite Identification

Common Name

Aspartylglycosamine

Description

Aspartylglycosamine, also known as n4-(beta-N-acetyl-D-glucosaminyl)-L-asparagine or 1-beta-aspartyl-N-acetyl-D-glucosaminylamine, is a member of the class of compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Aspartylglycosamine is soluble (in water) and a moderately acidic compound (based on its pKa). Aspartylglycosamine can be found primarily in urine, as well as in human spleen tissue. Within the cell, aspartylglycosamine is primarily located in the cytoplasm. Moreover, aspartylglycosamine is found to be associated with aspartylglucosaminuria, which is an inborn error of metabolism. Large amount of aspartylglycosamine appears in patients with aspartylglycosaminuria corresponding to decreased activity of aspartylglycosamine amido hydrolase.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000489
     RDKit          3D
Aspartylglycosamine
 44 44  0  0  0  0  0  0  0  0999 V2000
   -0.9245   -2.0528   -3.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518   -1.7239   -2.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1228   -2.6035   -1.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290   -0.4492   -1.5899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175   -0.0861   -0.3037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6180    0.2078    0.7031 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4430   -0.7418    0.6852 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7656   -0.3220    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938    0.8886    0.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.2670    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867   -0.5593    0.0490 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1664    0.0949   -1.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3439   -1.4879    0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5527   -2.1721    1.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2092   -1.6215   -0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198    0.3210    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9316    1.5044    1.9730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3698    1.9541    3.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336    2.1718    4.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.3050    1.0864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9881    2.3860    1.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975    1.1589   -0.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5824    1.0984   -1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4978   -2.9104   -3.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0749   -1.2258   -4.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687   -2.2424   -3.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    0.2385   -2.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -0.9655    0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501    1.2390    0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -1.7472    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0463   -1.7109    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -2.1272   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424    0.2374    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1313    1.1259   -1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.3139   -1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2222   -1.6733   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935    2.2685    1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1597    1.2892    3.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785    2.9504    3.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7370    2.4819    5.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539    0.3683    1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8969    2.1122    1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9111    2.0181   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3485    0.5836   -0.8873 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  6
  7 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  1
 12 34  1  0
 12 35  1  0
 15 36  1  0
 17 37  1  6
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  1
 21 42  1  0
 22 43  1  6
 23 44  1  0
M  END


  Mrv0541 02231218332D          

 23 23  0  0  1  0            999 V2000
   13.7416   -4.5907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7427   -5.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4587   -5.8321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1755   -5.4182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1755   -4.5905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4586   -4.1766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0271   -4.1782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8899   -4.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4587   -6.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8899   -5.8307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3125   -4.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5982   -4.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8837   -4.5909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1693   -4.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4549   -4.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1693   -3.3534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3125   -5.4159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8837   -5.4159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4586   -3.3516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1731   -2.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1731   -2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8875   -3.3516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7442   -7.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  1  0  0  0
  3  9  1  1  0  0  0
  4 10  1  6  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 11 17  2  0  0  0  0
 13 18  1  6  0  0  0
  6 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  9 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000350

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H21N3O8/c1-4(17)14-8-10(20)9(19)6(3-16)23-11(8)15-7(18)2-5(13)12(21)22/h5-6,8-11,16,19-20H,2-3,13H2,1H3,(H,14,17)(H,15,18)(H,21,22)/t5-,6+,8+,9+,10+,11+/m0/s1

> <INCHI_KEY>
YTTRPBWEMMPYSW-HRRFRDKFSA-N

> <FORMULA>
C12H21N3O8

> <MOLECULAR_WEIGHT>
335.3104

> <EXACT_MASS>
335.132864663

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
31.802894043023446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}propanoic acid

> <ALOGPS_LOGP>
-3.12

> <JCHEM_LOGP>
-6.7676290688800425

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.564777451206412

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.576209055900363

> <JCHEM_PKA_STRONGEST_BASIC>
8.432605335669903

> <JCHEM_POLAR_SURFACE_AREA>
191.44

> <JCHEM_REFRACTIVITY>
72.015

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.91e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylglucosaminylasparagine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000489
     RDKit          3D
Aspartylglycosamine
 44 44  0  0  0  0  0  0  0  0999 V2000
   -0.9245   -2.0528   -3.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518   -1.7239   -2.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1228   -2.6035   -1.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290   -0.4492   -1.5899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175   -0.0861   -0.3037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6180    0.2078    0.7031 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4430   -0.7418    0.6852 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7656   -0.3220    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938    0.8886    0.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.2670    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867   -0.5593    0.0490 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1664    0.0949   -1.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3439   -1.4879    0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5527   -2.1721    1.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2092   -1.6215   -0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198    0.3210    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9316    1.5044    1.9730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3698    1.9541    3.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336    2.1718    4.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.3050    1.0864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9881    2.3860    1.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975    1.1589   -0.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5824    1.0984   -1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4978   -2.9104   -3.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0749   -1.2258   -4.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687   -2.2424   -3.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    0.2385   -2.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -0.9655    0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501    1.2390    0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -1.7472    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0463   -1.7109    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -2.1272   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424    0.2374    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1313    1.1259   -1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.3139   -1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2222   -1.6733   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935    2.2685    1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1597    1.2892    3.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785    2.9504    3.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7370    2.4819    5.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539    0.3683    1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8969    2.1122    1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9111    2.0181   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3485    0.5836   -0.8873 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  6
  7 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  1
 12 34  1  0
 12 35  1  0
 15 36  1  0
 17 37  1  6
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  1
 21 42  1  0
 22 43  1  6
 23 44  1  0
M  END

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  C   UNK     0      25.651  -8.569   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      25.653 -10.116   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      26.990 -10.887   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.328 -10.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.328  -8.569   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.989  -7.796   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      24.317  -7.799   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      29.661  -7.799   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      26.990 -12.427   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      29.661 -10.884   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      22.983  -8.569   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.650  -7.800   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.316  -8.570   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.983  -7.800   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.649  -8.570   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      18.983  -6.260   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      22.983 -10.110   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      20.316 -10.110   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      26.989  -6.256   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      28.323  -5.487   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.323  -3.947   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      29.657  -6.256   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      25.656 -13.196   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1   19                                                  
CONECT    7    1   11                                                       
CONECT    8    5                                                            
CONECT    9    3   23                                                       
CONECT   10    4                                                            
CONECT   11    7   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11                                                            
CONECT   18   13                                                            
CONECT   19    6   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    9                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0000489
HETATM    1  C1  UNL     1      -0.924  -2.053  -3.546  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.452  -1.724  -2.210  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.123  -2.604  -1.598  1.00  0.00           O  
HETATM    4  N1  UNL     1      -1.229  -0.449  -1.590  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.718  -0.086  -0.304  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.618   0.208   0.703  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.443  -0.742   0.685  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.766  -0.322   0.407  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.994   0.889   0.176  1.00  0.00           O  
HETATM   10  C6  UNL     1       2.904  -1.267   0.377  1.00  0.00           C  
HETATM   11  C7  UNL     1       4.187  -0.559   0.049  1.00  0.00           C  
HETATM   12  N3  UNL     1       4.166   0.095  -1.229  1.00  0.00           N  
HETATM   13  C8  UNL     1       5.344  -1.488   0.105  1.00  0.00           C  
HETATM   14  O3  UNL     1       5.553  -2.172   1.148  1.00  0.00           O  
HETATM   15  O4  UNL     1       6.209  -1.621  -0.974  1.00  0.00           O  
HETATM   16  O5  UNL     1      -1.220   0.321   1.966  1.00  0.00           O  
HETATM   17  C9  UNL     1      -1.932   1.504   1.973  1.00  0.00           C  
HETATM   18  C10 UNL     1      -2.370   1.954   3.333  1.00  0.00           C  
HETATM   19  O6  UNL     1      -1.334   2.172   4.203  1.00  0.00           O  
HETATM   20  C11 UNL     1      -3.143   1.305   1.086  1.00  0.00           C  
HETATM   21  O7  UNL     1      -3.988   2.386   1.201  1.00  0.00           O  
HETATM   22  C12 UNL     1      -2.597   1.159  -0.332  1.00  0.00           C  
HETATM   23  O8  UNL     1      -3.582   1.098  -1.279  1.00  0.00           O  
HETATM   24  H1  UNL     1      -1.498  -2.910  -3.946  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.075  -1.226  -4.271  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.169  -2.242  -3.533  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.671   0.238  -2.137  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.293  -0.966   0.100  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.250   1.239   0.471  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.282  -1.747   0.871  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.046  -1.711   1.405  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.716  -2.127  -0.304  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.342   0.237   0.816  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.131   1.126  -1.187  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.421  -0.314  -1.868  1.00  0.00           H  
HETATM   36  H13 UNL     1       7.222  -1.673  -0.843  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.294   2.268   1.488  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.160   1.289   3.734  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.878   2.950   3.181  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.737   2.482   5.067  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.654   0.368   1.399  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.897   2.112   1.409  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.911   2.018  -0.478  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.349   0.584  -0.887  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5   27
CONECT    5    6   22   28
CONECT    6    7   16   29
CONECT    7    8   30
CONECT    8    9    9   10
CONECT   10   11   31   32
CONECT   11   12   13   33
CONECT   12   34   35
CONECT   13   14   14   15
CONECT   15   36
CONECT   16   17
CONECT   17   18   20   37
CONECT   18   19   38   39
CONECT   19   40
CONECT   20   21   22   41
CONECT   21   42
CONECT   22   23   43
CONECT   23   44
END

HMDB0000489
     RDKit          3D
Aspartylglycosamine
 44 44  0  0  0  0  0  0  0  0999 V2000
   -0.9245   -2.0528   -3.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518   -1.7239   -2.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1228   -2.6035   -1.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290   -0.4492   -1.5899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175   -0.0861   -0.3037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6180    0.2078    0.7031 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4430   -0.7418    0.6852 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7656   -0.3220    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938    0.8886    0.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.2670    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867   -0.5593    0.0490 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1664    0.0949   -1.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3439   -1.4879    0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5527   -2.1721    1.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2092   -1.6215   -0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198    0.3210    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9316    1.5044    1.9730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3698    1.9541    3.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336    2.1718    4.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.3050    1.0864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9881    2.3860    1.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975    1.1589   -0.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5824    1.0984   -1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4978   -2.9104   -3.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0749   -1.2258   -4.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687   -2.2424   -3.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    0.2385   -2.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -0.9655    0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501    1.2390    0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -1.7472    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0463   -1.7109    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -2.1272   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424    0.2374    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1313    1.1259   -1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.3139   -1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2222   -1.6733   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935    2.2685    1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1597    1.2892    3.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785    2.9504    3.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7370    2.4819    5.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539    0.3683    1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8969    2.1122    1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9111    2.0181   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3485    0.5836   -0.8873 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  6
  7 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  1
 12 34  1  0
 12 35  1  0
 15 36  1  0
 17 37  1  6
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  1
 21 42  1  0
 22 43  1  6
 23 44  1  0
M  END

Synonyms

Value	Source
1-beta-Aspartyl-N-acetyl-D-glucosaminylamine	ChEBI
2-Acetamido-1-(beta-L-aspartamido)-1,2-dideoxy-beta-D-glucose	ChEBI
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamine	ChEBI
2-Acetamido-N-L-beta-aspartyl-2-deoxy-beta-D-glucopyranosylamine	ChEBI
2-Acetamido-N(1)-L-beta-aspartyl-2-deoxy-beta-D-glucopyranosylamine	ChEBI
AADG	ChEBI
beta-N-Acetylglucosaminyl-L-asparagine	ChEBI
N-Acetylglucosaminylasparagine	ChEBI
N4-(Acetyl-beta-D-glucosaminyl)asparagine	ChEBI
N4-(beta-N-Acetyl-D-glucosaminyl)-L-asparagine	ChEBI
1-b-Aspartyl-N-acetyl-D-glucosaminylamine	Generator
1-Β-aspartyl-N-acetyl-D-glucosaminylamine	Generator
2-Acetamido-1-(b-L-aspartamido)-1,2-dideoxy-b-D-glucose	Generator
2-Acetamido-1-(β-L-aspartamido)-1,2-dideoxy-β-D-glucose	Generator
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-b-D-glucopyranosylamine	Generator
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine	Generator
2-Acetamido-N-L-b-aspartyl-2-deoxy-b-D-glucopyranosylamine	Generator
2-Acetamido-N-L-β-aspartyl-2-deoxy-β-D-glucopyranosylamine	Generator
2-Acetamido-N(1)-L-b-aspartyl-2-deoxy-b-D-glucopyranosylamine	Generator
2-Acetamido-N(1)-L-β-aspartyl-2-deoxy-β-D-glucopyranosylamine	Generator
b-N-Acetylglucosaminyl-L-asparagine	Generator
Β-N-acetylglucosaminyl-L-asparagine	Generator
N4-(Acetyl-b-D-glucosaminyl)asparagine	Generator
N4-(Acetyl-β-D-glucosaminyl)asparagine	Generator
N4-(b-N-Acetyl-D-glucosaminyl)-L-asparagine	Generator
N4-(Β-N-acetyl-D-glucosaminyl)-L-asparagine	Generator
(N-g-(2-Acetamido-2-deoxy-b-D-gluco-pyranosyl)-L-asparagine	HMDB
(N-gamma-(2-Acetamido-2-deoxy-beta-D-gluco-pyranosyl)-L-asparagine	HMDB
(N-gamma-(2-Acetamido-2-deoxy-beta-delta-gluco-pyranosyl)-L-asparagine	HMDB
2-Acetamido-1-b-(L-aspartamido)-1,2-dideoxy-D-glucose	HMDB
2-Acetamido-1-beta-(L-aspartamido)-1,2-dideoxy-D-glucose	HMDB
2-Acetamido-1-beta-(L-aspartamido)-1,2-dideoxy-delta-glucose	HMDB
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-delta-glucopyranosylamine	HMDB
4-N-2-Acetamido-2-deoxy-beta-D-glucopyranosyl-L-asparagine	HMDB
4-N-2-Acetamido-2-deoxy-beta-delta-glucopyranosyl-L-asparagine	HMDB
Acetylglucosaminylasparagine	HMDB
Asparaginylglucosamine	HMDB
Aspartylglucosamine	HMDB
Aspartylglucosylamine	HMDB
b-D-GlcNAc-1->n-asn	HMDB
beta-D-GlcNAc-1->n-asn	HMDB
beta-delta-GlcNAc-1->n-asn	HMDB
H-Asn(glcnac-b-D)-OH	HMDB
H-Asn(glcnac-beta-D)-OH	HMDB
N(4)-(Acetyl-beta-D-glucosaminyl)asparagine	HMDB
N(4)-(beta-N-Acetyl-D-glucosaminyl)-L-asparagine	HMDB
N-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)L-asparagine	HMDB
N-(2-(Acetylamino)-2-deoxy-beta-delta-glucopyranosyl)L-asparagine	HMDB
N-(2-Acetylamino)-2-deoxy-beta-D-glucopyranosyl-L-asparagine	HMDB
N-(2-Acetylamino)-2-deoxy-beta-delta-glucopyranosyl-L-asparagine	HMDB
N(4)-(2-Acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine	HMDB
N(4)-(2-Acetamido-2-deoxyglucopyranosyl)asparagine	HMDB
N-ADGP-asn	HMDB
N(4)-(b-N-Acetyl-D-glucosaminyl)-L-asparagine	HMDB
N(4)-(Β-N-acetyl-D-glucosaminyl)-L-asparagine	HMDB
Aspartylglycosamine	MeSH

Molecular Formula

C₁₂H₂₁N₃O₈

Average Mass

335.3104

Monoisotopic Mass

335.132864663

IUPAC Name

(2S)-2-amino-3-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}propanoic acid

Traditional Name

acetylglucosaminylasparagine

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1NC(=O)C[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C12H21N3O8/c1-4(17)14-8-10(20)9(19)6(3-16)23-11(8)15-7(18)2-5(13)12(21)22/h5-6,8-11,16,19-20H,2-3,13H2,1H3,(H,14,17)(H,15,18)(H,21,22)/t5-,6+,8+,9+,10+,11+/m0/s1

InChI Key

YTTRPBWEMMPYSW-HRRFRDKFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

Hexose monosaccharide
N-glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Monosaccharide
Oxane
Amino acid or derivatives
Amino acid
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxide
Carbonyl group
Primary aliphatic amine
Alcohol
Organonitrogen compound
Primary amine
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N(4)-glycosyl-L-asparagine (CHEBI:17261 )
glucosaminylamine (CHEBI:17261 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	39.1 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-6.8	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	1.58	ChemAxon
pKa (Strongest Basic)	8.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	191.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	31.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Placenta
Spleen
Urine

Tissue Locations

Placenta
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Aspartylglucosaminuria		Association	Human Urine	HMDB	6787338
Aspartylglucosaminuria	Increased	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Aspartylglucosaminuria		Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	3	Human stool; Human feces; Human urine; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	2	Human feces; Human urine; Human sputum; Human ; Human saliva; Human subgingival plaque; Human vaginal fluid; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Urine	Detected and Quantified	70.383	30.420	97.621	umol/mmol creatinine	Children (1-13 years old)	Both	Aspartylglucosaminuria	HMDB	6787338
Human Urine	Detected and Quantified	87.680	39.963	166.0153	umol/mmol creatinine	Adult (>18 years old)	Both	Aspartylglucosaminuria	HMDB	6787338
Human Urine	Detected and Quantified	0			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	6787338
Human Urine	Detected and Quantified	0			umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	HMDB	6787338
Human Urine	Detected and Quantified	0.6	0.20	1.00	umol/mmol creatinine	Adult (>18 years old)	Both	Aspartylglucosaminuria	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	175.0	100.0	250.0	umol/mmol creatinine	Children (1-13 years old)	Both	Aspartylglucosaminuria	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified								HMDB

External Links

HMDB ID

HMDB0000489

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022071

KNApSAcK ID

Not Available

Chemspider ID

110370

KEGG Compound ID

C04540

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5476

PubChem Compound

123826

PDB ID

Not Available

ChEBI ID

17261

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Haltia M, Palo J, Autio S: Aspartylglycosaminuria: a generalized storage disease. Morphological and histochemical studies. Acta Neuropathol. 1975;31(3):243-55. doi: 10.1007/BF00684563. [PubMed:1138532 ]
Mononen T, Mononen I, Matilainen R, Airaksinen E: High prevalence of aspartylglycosaminuria among school-age children in eastern Finland. Hum Genet. 1991 Jul;87(3):266-8. doi: 10.1007/BF00200902. [PubMed:1864600 ]
Mononen I, Kaartinen V, Mononen T: Amniotic fluid glycoasparagines in fetal aspartylglycosaminuria. J Inherit Metab Dis. 1988;11(2):194-8. doi: 10.1007/BF01799872. [PubMed:3139932 ]
Mononen I, Kaartinen V, Mononen T: Laboratory detection of aspartylglycosaminuria. Scand J Clin Lab Invest Suppl. 1988;191:7-11. [PubMed:3247584 ]
Hoffmann GF, Seppel CK, Holmes B, Mitchell L, Christen HJ, Hanefeld F, Rating D, Nyhan WL: Quantitative organic acid analysis in cerebrospinal fluid and plasma: reference values in a pediatric population. J Chromatogr. 1993 Jul 23;617(1):1-10. doi: 10.1016/0378-4347(93)80414-y. [PubMed:8376520 ]
Jalanko A, Tenhunen K, McKinney CE, LaMarca ME, Rapola J, Autti T, Joensuu R, Manninen T, Sipila I, Ikonen S, Riekkinen P Jr, Ginns EI, Peltonen L: Mice with an aspartylglucosaminuria mutation similar to humans replicate the pathophysiology in patients. Hum Mol Genet. 1998 Feb;7(2):265-72. doi: 10.1093/hmg/7.2.265. [PubMed:9425233 ]
Dunder U, Kaartinen V, Valtonen P, Vaananen E, Kosma VM, Heisterkamp N, Groffen J, Mononen I: Enzyme replacement therapy in a mouse model of aspartylglycosaminuria. FASEB J. 2000 Feb;14(2):361-7. doi: 10.1096/fasebj.14.2.361. [PubMed:10657992 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Aspartylglycosamine (MMDBc0000350)

MOL for #<Metabolite:0x00007f9230641670>

3D MOL for #<Metabolite:0x00007f9230641670>

3D SDF for #<Metabolite:0x00007f9230641670>

3D-SDF for #<Metabolite:0x00007f9230641670>

PDB for #<Metabolite:0x00007f9230641670>

3D PDB for #<Metabolite:0x00007f9230641670>

SMILES for #<Metabolite:0x00007f9230641670>

INCHI for #<Metabolite:0x00007f9230641670>

Structure for #<Metabolite:0x00007f9230641670>

3D Structure for #<Metabolite:0x00007f9230641670>