NP-MRD: Showing NP-Card for {[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid (NP0291310)

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Record Information

Version

2.0

Created at

2022-09-09 22:21:14 UTC

Updated at

2022-09-09 22:21:14 UTC

NP-MRD ID

NP0291310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid

Description

UDP-D-glucose, also known as UDP-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. UDP-D-glucose is an extremely weak basic (essentially neutral) compound (based on its pKa). UDP-D-glucose may be a unique S. {[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid is found in Apis cerana. Cerevisiae (yeast) metabolite.

Structure

MOL 3D 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

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   10.1122    2.4085   -0.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0785    1.6893   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7939    0.9173    0.9067 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6387    0.1278    0.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7882    0.1019   -0.1125 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5861   -0.6815   -0.1612 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5881   -0.0605   -0.9409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4967   -0.8887   -0.7259 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1916   -0.2457   -1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9479    0.9047   -0.3245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897    1.6245   -0.7085 P   0  0  1  0  0  5  0  0  0  0  0  0
    0.6737    3.1348   -0.5441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284    1.3595   -2.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    1.1908    0.3820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806    0.5459   -0.4635 P   0  0  2  0  0  5  0  0  0  0  0  0
   -1.6609   -0.6730   -1.2603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    1.6915   -1.5337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415    0.1523    0.6713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121   -0.0135    0.1184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3431    0.9168    0.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6593    0.8372    0.2755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4524    1.8557    1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7970    1.8578    0.7167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1810   -0.5356    0.7079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5310   -0.6597    0.4481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3986   -1.5678   -0.0734 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8896   -2.8470    0.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -1.4348    0.3148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1248   -2.2375   -0.4832 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056   -1.2713    0.7235 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5392   -2.6722    0.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8830   -0.7802    1.1716 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4511   -1.7385    2.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0879    0.8630   -1.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3185    0.8672   -2.1752 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2067    1.6394   -1.2244 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4683    0.9291    1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4082   -0.4788    1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7314   -1.7066   -0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -1.7758   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3850   -0.9634   -0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981   -0.0566   -2.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048    2.0058   -2.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0871    2.4531   -1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4203    0.1652   -0.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7711    0.9765   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9918    2.8628    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3777    1.5138    2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8840    1.5713   -0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9483   -0.6068    1.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0881   -0.4205    1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5572   -1.3372   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3089   -3.2400    0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8754   -1.7491    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3363   -2.4785    0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6950   -0.8358    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698   -3.0448   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7675    0.1947    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4990   -2.5896    1.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4269    2.2324   -2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 15 18  1  1
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 15 16  2  0
 15 14  1  0
 11 14  1  1
 11 13  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6 32  1  0
 32 33  1  0
 32 30  1  0
 30 31  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 36  1  0
 36 34  1  0
 34 35  2  0
 19 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 21  1  0
 30  8  1  0
 34  5  1  0
 23 49  1  0
 22 47  1  0
 22 48  1  0
 21 46  1  6
 19 45  1  6
 17 44  1  0
 13 43  1  0
  9 41  1  0
  9 42  1  0
  8 40  1  6
  6 39  1  6
 32 58  1  1
 33 59  1  0
 30 56  1  1
 31 57  1  0
  4 38  1  0
  3 37  1  0
 36 60  1  0
 28 54  1  1
 29 55  1  0
 26 52  1  6
 27 53  1  0
 24 50  1  1
 25 51  1  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>
NP0291310

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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

Chemical Formula

C₁₅H₂₄N₂O₁₇P₂

Average Mass

566.3018 Da

Monoisotopic Mass

566.05502 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid (NP0291310)

MOL for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D MOL for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D SDF for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D-SDF for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

PDB for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D PDB for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

SMILES for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

INCHI for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

Structure for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D Structure for NP0291310 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)