MiMeDB: Showing metabocard for Hyaluronan biosynthesis, precursor 1 (MMDBc0048918)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:15:33 UTC

Update Date

2024-04-30 20:37:44 UTC

Metabolite ID

MMDBc0048918

Metabolite Identification

Common Name

Hyaluronan biosynthesis, precursor 1

Description

beta-D-4-deoxy-Delta(4)-GlcpA-(1->3)-beta-D-GlcpNAc(1-), also known as β-D-4-deoxy-δ(4)-glca-(1->3)-β-D-glcnac(1), belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Based on a literature review very few articles have been published on beta-D-4-deoxy-Delta(4)-GlcpA-(1->3)-beta-D-GlcpNAc(1-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304302200152D          

 46 47  0  0  1  0            999 V2000
   -1.4289    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091   -0.3645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    0.2768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -4.4270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.5230    0.0000 H   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
  3  5  1  0  0  0  0
  6  3  1  6  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  6  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  6  0  0  0
 34 35  1  0  0  0  0
 32 36  1  0  0  0  0
 26 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  6  0  0  0
 38 39  1  0  0  0  0
 29 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 23 43  1  0  0  0  0
  6 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  6  0  0  0
 45 46  1  0  0  0  0
M  CHG  1  41  -1
M  END


  Mrv1652304302200152D          

 46 47  0  0  1  0            999 V2000
   -1.4289    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1091   -0.3645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    0.2768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -4.4270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.5230    0.0000 H   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
  3  5  1  0  0  0  0
  6  3  1  6  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  6  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  6  0  0  0
 34 35  1  0  0  0  0
 32 36  1  0  0  0  0
 26 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  6  0  0  0
 38 39  1  0  0  0  0
 29 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 23 43  1  0  0  0  0
  6 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  6  0  0  0
 45 46  1  0  0  0  0
M  CHG  1  41  -1
M  END
> <DATABASE_ID>
MMDBc0048918

> <DATABASE_NAME>
MIME

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@@]([H])(O[C@]2([H])OC(=C([H])[C@]([H])(O[H])[C@@]2([H])O[H])C([O-])=O)[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H21NO11/c1-4(17)15-8-11(10(20)7(3-16)24-13(8)23)26-14-9(19)5(18)2-6(25-14)12(21)22/h2,5,7-11,13-14,16,18-20,23H,3H2,1H3,(H,15,17)(H,21,22)/p-1/t5-,7+,8+,9+,10+,11+,13+,14-/m0/s1

> <INCHI_KEY>
DLGJWSVWTWEWBJ-UCFDOFRFSA-M

> <FORMULA>
C14H20NO11

> <MOLECULAR_WEIGHT>
378.311

> <EXACT_MASS>
378.104184048

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.138368677696825

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylate

> <ALOGPS_LOGP>
-1.97

> <JCHEM_LOGP>
-3.9322067576666666

> <ALOGPS_LOGS>
-0.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.50871934792074

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1697574854228674

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5730828756651856

> <JCHEM_POLAR_SURFACE_AREA>
198.07

> <JCHEM_REFRACTIVITY>
90.50350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,6R)-6-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-22         0                                  
HETATM    1  H   UNK     0      -2.667   1.540   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       0.204  -0.680   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0      -0.487   0.517   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM    8  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -2.667  -6.160   0.000  0.00  0.00           H+0
HETATM   11  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      -5.335  -4.620   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.000  -6.160   0.000  0.00  0.00           H+0
HETATM   15  N   UNK     0      -1.334  -6.930   0.000  0.00  0.00           N+0
HETATM   16  H   UNK     0      -0.564  -8.264   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -4.207  -9.240   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.667 -10.780   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.127  -9.240   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       2.667  -6.160   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       6.668  -2.310   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0       5.335  -6.160   0.000  0.00  0.00           H+0
HETATM   34  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   35  H   UNK     0       8.208  -5.390   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   38  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   39  H   UNK     0       4.001  -8.470   0.000  0.00  0.00           H+0
HETATM   40  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0      -1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   45  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   46  H   UNK     0       2.104  -0.976   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7    8   43                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   13                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    9   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   13   24   25   43                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28   36                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   40                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34   36                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   32   26   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   29   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   23    6   44   45                                             
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   94    0
END

Synonyms

Value	Source
beta-D-4-Deoxy-Delta(4)-glca-(1->3)-beta-D-glcnac(1)	ChEBI
beta-D-4-Deoxy-Delta(4)-glcpa-(1->3)-beta-D-glcpnac	ChEBI
b-D-4-Deoxy-delta(4)-glca-(1->3)-b-D-glcnac(1)	Generator
Β-D-4-deoxy-δ(4)-glca-(1->3)-β-D-glcnac(1)	Generator
b-D-4-Deoxy-delta(4)-glcpa-(1->3)-b-D-glcpnac	Generator
Β-D-4-deoxy-δ(4)-glcpa-(1->3)-β-D-glcpnac	Generator
b-D-4-Deoxy-delta(4)-glcpa-(1->3)-b-D-glcpnac(1-)	Generator
Β-D-4-deoxy-δ(4)-glcpa-(1->3)-β-D-glcpnac(1-)	Generator

Molecular Formula

C₁₄H₂₀NO₁₁

Average Mass

378.311

Monoisotopic Mass

378.104184048

IUPAC Name

(2R,3R,4S)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylate

Traditional Name

(4S,5R,6R)-6-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@@]([H])(O[C@]2([H])OC(=C([H])[C@]([H])(O[H])[C@@]2([H])O[H])C([O-])=O)[C@]1([H])O[H]

InChI Identifier

InChI=1S/C14H21NO11/c1-4(17)15-8-11(10(20)7(3-16)24-13(8)23)26-14-9(19)5(18)2-6(25-14)12(21)22/h2,5,7-11,13-14,16,18-20,23H,3H2,1H3,(H,15,17)(H,21,22)/p-1/t5-,7+,8+,9+,10+,11+,13+,14-/m0/s1

InChI Key

DLGJWSVWTWEWBJ-UCFDOFRFSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Disaccharide
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary alcohol
Secondary carboxylic acid amide
Acetal
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organopnictogen compound
Primary alcohol
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbohydrate acid derivative anion (CHEBI:63280 )
monocarboxylic acid anion (CHEBI:63280 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	102 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.9	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	198.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.5 m³·mol⁻¹	ChemAxon
Polarizability	34.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001312	Water	N-Acetyl-D-glucosamine	Glucuronidase, beta	Beta-Glucuronidase, Lysosomal	VMH	3468507 3924735 3987656
MMDBr0001416	Uridine diphosphate-N-acetylglucosamine	Hydrogen Ion	Hyaluronan synthase 1	Hyaluronan Synthase	VMH	12512858 8651928 8798477 8798544 9083017
MMDBr0001417	Hyaluronan biosynthesis, precursor 1	Hydrogen Ion	Hyaluronan synthase 1	Hyaluronan Synthase	VMH	12512858 8651928 8798477 8798544 9083017
MMDBr0008406	Water	N-Acetyl-D-glucosamine	Not Available	Beta-glucuronidase, hyaluronan degradation	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	4	Human feces; Human	Metabolic reconstruction
Bacteria	Firmicutes	1	Human ; Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26333072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25200971

PDB ID

Not Available

ChEBI ID

63280

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for Hyaluronan biosynthesis, precursor 1 (MMDBc0048918)

MOL for #<Metabolite:0x00007fa4df413a58>

3D MOL for #<Metabolite:0x00007fa4df413a58>

3D SDF for #<Metabolite:0x00007fa4df413a58>

3D-SDF for #<Metabolite:0x00007fa4df413a58>

PDB for #<Metabolite:0x00007fa4df413a58>

3D PDB for #<Metabolite:0x00007fa4df413a58>

SMILES for #<Metabolite:0x00007fa4df413a58>

INCHI for #<Metabolite:0x00007fa4df413a58>

Structure for #<Metabolite:0x00007fa4df413a58>

3D Structure for #<Metabolite:0x00007fa4df413a58>