MiMeDB: Showing metabocard for UDP-D-glucose (MMDBc0032979)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:29:44 UTC

Update Date

2024-04-30 19:57:40 UTC

Metabolite ID

MMDBc0032979

Metabolite Identification

Common Name

UDP-D-glucose

Description

Uridine diphosphate glucose, also known as UDP-glucose or UDP-alpha-D-glucose, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphate glucose exists in all living species, ranging from bacteria to plants to humans. Uridine diphosphate glucose is a key intermediate in carbohydrate metabolism. For instance, UDP-glucose is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid. UDP-glucose can also be used as a precursor for the biosynthesis of sucrose, lipopolysaccharides and glycosphingolipids. Within humans, uridine diphosphate glucose participates in a number of enzymatic reactions. In particular, ceramide (D18:1/18:0) and uridine diphosphate glucose can be converted into glucosylceramide (D18:1/18:0) and uridine 5'-diphosphate through the action of the enzyme ceramide glucosyltransferase. In addition, glucosylceramide (D18:1/18:0) and uridine diphosphate glucose can be biosynthesized from lactosylceramide (D18:1/18:0) and uridine 5'-diphosphate through its interaction with the enzyme Beta-1,4-galactosyltransferase 6.

Structure

MOL SDF PDB SMILES InChI

ChEBI
  Mrv0541 02241222182D          

 36 38  0  0  1  0            999 V2000
   23.8665  -10.1557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.6570   -9.8980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2237   -9.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6259  -10.9634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.2756  -10.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8288   -9.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5535  -10.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.7975  -10.9634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.1105  -11.6267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0626  -10.1867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1106  -11.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6055   -8.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7665   -9.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3095  -11.6232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2310   -9.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1823  -10.4960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0146   -9.1212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3608  -10.4960    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.5394  -10.4960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3574  -11.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3574   -9.6746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7180  -10.4926    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.7111  -11.3140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7111   -9.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8932  -10.4926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1787  -10.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1787  -11.7301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8932  -12.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7498  -11.7301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0353  -12.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4643  -12.1426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7498  -10.9051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0353  -10.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3208  -10.9051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4643  -10.4926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4643  -12.9676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  1  0  0  0
  7  8  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 22 24  2  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 35 26  1  0  0  0  0
 35 32  1  0  0  0  0
 32 29  1  0  0  0  0
 29 31  1  0  0  0  0
 31 27  1  0  0  0  0
 27 28  1  6  0  0  0
 29 30  1  6  0  0  0
 31 36  1  1  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
M  END

ChEBI
  Mrv0541 02241222182D          

 36 38  0  0  1  0            999 V2000
   23.8665  -10.1557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.6570   -9.8980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2237   -9.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6259  -10.9634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.2756  -10.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8288   -9.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5535  -10.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.7975  -10.9634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.1105  -11.6267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0626  -10.1867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1106  -11.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6055   -8.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7665   -9.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3095  -11.6232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2310   -9.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1823  -10.4960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0146   -9.1212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3608  -10.4960    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.5394  -10.4960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3574  -11.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3574   -9.6746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7180  -10.4926    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.7111  -11.3140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7111   -9.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8932  -10.4926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1787  -10.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1787  -11.7301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8932  -12.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7498  -11.7301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0353  -12.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4643  -12.1426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7498  -10.9051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0353  -10.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3208  -10.9051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4643  -10.4926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4643  -12.9676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  1  0  0  0
  7  8  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 22 24  2  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 35 26  1  0  0  0  0
 35 32  1  0  0  0  0
 32 29  1  0  0  0  0
 29 31  1  0  0  0  0
 31 27  1  0  0  0  0
 27 28  1  6  0  0  0
 29 30  1  6  0  0  0
 31 36  1  1  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032979

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14?/m1/s1

> <INCHI_KEY>
HSCJRCZFDFQWRP-RDKQLNKOSA-N

> <FORMULA>
C15H24N2O17P2

> <MOLECULAR_WEIGHT>
566.3018

> <EXACT_MASS>
566.055020376

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
45.33925165851529

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-1.43

> <JCHEM_LOGP>
-4.996608078666667

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1563251336694855

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7326003066859688

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6484093801081894

> <JCHEM_POLAR_SURFACE_AREA>
291.54

> <JCHEM_REFRACTIVITY>
106.45579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
udp-glc

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      44.551 -18.957   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      46.026 -18.476   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0      43.351 -18.078   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      44.102 -20.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.181 -19.503   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      46.347 -16.969   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      42.100 -18.996   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.555 -20.465   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      45.006 -21.703   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      48.650 -19.015   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      46.873 -21.004   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      47.797 -16.474   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.631 -18.521   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      41.644 -21.697   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      48.965 -17.507   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      39.540 -19.593   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      50.427 -17.026   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0      38.007 -19.593   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0      36.474 -19.593   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      38.000 -21.126   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      38.000 -18.059   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      34.940 -19.586   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      34.927 -21.119   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      34.927 -18.046   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      33.401 -19.586   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      32.067 -20.356   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.067 -21.896   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      33.401 -22.666   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      29.400 -21.896   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      28.066 -22.666   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      30.733 -22.666   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.400 -20.356   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.066 -19.586   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      26.732 -20.356   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      30.733 -19.586   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      30.733 -24.206   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13    8                                                  
CONECT    8    4    7   14                                                  
CONECT    9    4                                                            
CONECT   10    5   15                                                       
CONECT   11    5                                                            
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    8                                                            
CONECT   15   10   12   17                                                  
CONECT   16   13   18                                                       
CONECT   17   15                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18   22                                                       
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   19   23   25   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   31   28                                                  
CONECT   28   27                                                            
CONECT   29   32   31   30                                                  
CONECT   30   29                                                            
CONECT   31   29   27   36                                                  
CONECT   32   35   29   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   26   32                                                       
CONECT   36   31                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

Synonyms

Value	Source
UDP-GLC	ChEBI
UDP-Glucose	ChEBI
UDPglucose	ChEBI
Uridine 5'-(trihydrogen diphosphate), mono-alpha-D-glucopyranosyl ester	ChEBI
Uridine 5'-(trihydrogen diphosphate), p'-alpha-D-glucopyranosyl ester	ChEBI
Uridine diphosphate glucose	ChEBI
Uridinediphosphoglucose	ChEBI
Uridine 5'-(trihydrogen diphosphate), mono-a-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphate), mono-α-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphoric acid), mono-a-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphoric acid), mono-α-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphate), p'-a-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphate), p'-α-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphoric acid), p'-a-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphoric acid), p'-alpha-D-glucopyranosyl ester	Generator
Uridine 5'-(trihydrogen diphosphoric acid), p'-α-D-glucopyranosyl ester	Generator
Uridine diphosphoric acid glucose	Generator

Molecular Formula

C₁₅H₂₄N₂O₁₇P₂

Average Mass

566.3018

Monoisotopic Mass

566.055020376

IUPAC Name

[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

Traditional Name

udp-glc

CAS Registry Number

133-89-1

SMILES

OC[C@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14?/m1/s1

InChI Key

HSCJRCZFDFQWRP-RDKQLNKOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Urea
Secondary alcohol
Lactam
Polyol
Oxacycle
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-sugar (CHEBI:18066 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	15 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	291.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	106.46 m³·mol⁻¹	ChemAxon
Polarizability	45.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_32) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0901110000-4b81825405869909992e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3911000000-6fd09254750e77963110	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5900000000-03a2a98eb0aa84737530	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4901260000-8396a090c14de7f2d708	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-8907020000-94410556a0288cb8167b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-5901000000-10132c85ad33464d4eef	2016-09-12	View Spectrum

Biological Properties

Cellular Locations

Endoplasmic reticulum
Golgi apparatus

Biospecimen Locations

Blood
Liver
Skeletal Muscle
Urine

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

Not Available

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Firmicutes	372	Human feces; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human supragingival plaque; Human mucosa; Cattle ; Pig ; Human pleural fluid plaque	Metabolic reconstruction
Bacteria	Proteobacteria	174	Human feces; Human ; Human stool; Pig ; Human unknown; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human sputum	Metabolic reconstruction
Bacteria	Bacteroidetes	116	Human feces; Human stool; Human saliva; Human ; Human appendix biopsy	Metabolic reconstruction
Bacteria	Actinobacteria	119	Human feces; Human ; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque	Metabolic reconstruction
Bacteria	Fusobacteria	19	Human ; Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Tenericutes	2	Human feces	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	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	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	155.0	113.0	uM	Adult (>18 years old)	Both	Normal	HMDB	7877593
Human Urine	Detected and Quantified	0.993		umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Uridine diphosphate glucose

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18066

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Haugen HF, Skrede S: Nucleotide pyrophosphatase and phosphodiesterase I. Demonstration of activity in normal serum, and an increase in cholestatic liver disease. Scand J Gastroenterol. 1976;11(2):121-7. [PubMed:4880 ]
Schwartz AL, Rall TW: Hormonal regulation of glycogen metabolism in human fetal liver. II. Regulation of glycogen synthase activity. Diabetes. 1975 Dec;24(12):1113-22. doi: 10.2337/diab.24.12.1113. [PubMed:811498 ]
Marschall HU, Matern H, Wietholtz H, Egestad B, Matern S, Sjovall J: Bile acid N-acetylglucosaminidation. In vivo and in vitro evidence for a selective conjugation reaction of 7 beta-hydroxylated bile acids in humans. J Clin Invest. 1992 Jun;89(6):1981-7. doi: 10.1172/JCI115806. [PubMed:1602004 ]
Tarantino G, Morelli L, Califano C: [Uridine diphosphate glucose (UDPG) in the treatment of hepatic disease from chronic alcohol abuse]. Riv Eur Sci Med Farmacol. 1990 Apr;12(2):109-17. [PubMed:2080308 ]
Hers HG: Mechanisms of blood glucose homeostasis. J Inherit Metab Dis. 1990;13(4):395-410. doi: 10.1007/BF01799497. [PubMed:2122108 ]
Ng WG, Xu YK, Kaufman FR, Donnell GN: Deficit of uridine diphosphate galactose in galactosaemia. J Inherit Metab Dis. 1989;12(3):257-66. doi: 10.1007/BF01799215. [PubMed:2515367 ]
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. doi: 10.1016/s1570-0232(03)00277-0. [PubMed:12829005 ]
Nielsen JN, Richter EA: Regulation of glycogen synthase in skeletal muscle during exercise. Acta Physiol Scand. 2003 Aug;178(4):309-19. doi: 10.1046/j.1365-201X.2003.01165.x. [PubMed:12864735 ]
Raila J, Wirth K, Chen F, Buscher U, Dudenhausen JW, Schweigert FJ: Excretion of vitamin A in urine of women during normal pregnancy and pregnancy complications. Ann Nutr Metab. 2004 Sep-Oct;48(5):357-64. doi: 10.1159/000082003. Epub 2004 Nov 9. [PubMed:15542927 ]
Reynolds TH 4th, Pak Y, Harris TE, Manchester J, Barrett EJ, Lawrence JC Jr: Effects of insulin and transgenic overexpression of UDP-glucose pyrophosphorylase on UDP-glucose and glycogen accumulation in skeletal muscle fibers. J Biol Chem. 2005 Feb 18;280(7):5510-5. doi: 10.1074/jbc.M413614200. Epub 2004 Dec 13. [PubMed:15596435 ]
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 UDP-D-glucose (MMDBc0032979)

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