NP-MRD: Showing NP-Card for UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine (NP0062860)

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Record Information

Version

2.0

Created at

2022-04-28 07:24:18 UTC

Updated at

2022-04-28 07:24:18 UTC

NP-MRD ID

NP0062860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine

Description

2-{[(2R,3S,4R,5S,6S)-2-({[({[(2S,3S,4R,5S)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid 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-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine is found in Escherichia coli. Based on a literature review very few articles have been published on 2-{[(2R,3S,4R,5S,6S)-2-({[({[(2S,3S,4R,5S)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209242D          

 44 46  0  0  1  0            999 V2000
    2.8579    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  2  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 C   0  0  1  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
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
    2.5559    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    2.7770    0.0000 O   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    0.8250    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.8250    0.0000 O   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
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390   -2.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  4  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  1  0  0  0
 10 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  2  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
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 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  2  0  0  0  0
 24 33  1  0  0  0  0
 19 33  1  0  0  0  0
  3 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  2 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
  1 44  1  1  0  0  0
M  END

     RDKit          3D

 73 75  0  0  0  0  0  0  0  0999 V2000
   -6.3250    3.0490   -1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8618    1.8812   -0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1638    0.7046   -0.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8114    0.5576   -0.5185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6455    0.8096    0.9334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4323    1.4955    1.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871   -0.4458    1.7676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1675   -0.0039    3.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1110   -1.0655    4.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6421   -1.3426    1.3545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2901   -1.2929    0.0308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1993   -0.4220   -0.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051   -1.1832   -0.6323 P   0  0  1  0  0  5  0  0  0  0  0  0
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    2.6052    0.0412    1.3856 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740    0.6416    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718    0.4045    0.9555 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8516    0.9347    0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0187    0.4465    0.7543 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1857    0.6379   -0.0515 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3646    0.8651    0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5330    1.0590   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4296    1.0077   -1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4793    1.1806   -2.2232 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2271    0.7773   -2.0992 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1016    0.5911   -1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7430   -1.0022    1.0702 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.2312   -1.0643    0.9779 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8629   -1.6669   -0.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533   -0.8156   -0.9050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5101   -1.6919   -0.9793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8508   -2.3360   -2.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0261   -3.2338   -2.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -2.1509   -3.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1846    1.7943   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6842    0.6755    0.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8864    2.9861    0.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9544    0.8695    1.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4925    1.2431    0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1542    0.7391   -3.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6505   -2.4322   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
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 13 12  1  1
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  3  2  1  0
  2  1  2  3
  2 42  1  0
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 42 43  2  0
  4 37  1  0
 35 22  1  0
 31 25  1  0
 40 70  1  0
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 33 64  1  1
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 36 67  1  0
 26 61  1  0
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 30 63  1  0
  7 50  1  1
  8 51  1  0
  8 52  1  0
  9 53  1  0
  5 48  1  1
  6 49  1  0
  4 47  1  6
  1 45  1  0
  1 46  1  0
 44 73  1  0
M  END


  Mrv1652304282209242D          

 44 46  0  0  1  0            999 V2000
    2.8579    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  2  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 C   0  0  1  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
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7309    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3020   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390   -2.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  4  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  1  0  0  0
 10 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  2  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  2  0  0  0  0
 24 33  1  0  0  0  0
 19 33  1  0  0  0  0
  3 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  2 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
  1 44  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0062860

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/t9-,10-,12-,13+,14+,15+,16+,17-,19+/m0/s1

> <INCHI_KEY>
BEGZZYPUNCJHKP-FBZGRVJBSA-N

> <FORMULA>
C20H29N3O19P2

> <MOLECULAR_WEIGHT>
677.402

> <EXACT_MASS>
677.087049722

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.997907409714664

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.13

> <JCHEM_LOGP>
-4.638949203

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.03788539204872

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7303240065452128

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6465870252254513

> <JCHEM_POLAR_SURFACE_AREA>
326.71000000000004

> <JCHEM_REFRACTIVITY>
133.3058

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(2R,3S,4R,5S,6S)-2-[({[(2S,3S,4R,5S)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0       4.001   3.850   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0       4.771   2.516   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.231   5.184   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   14  P   UNK     0       2.667   1.540   0.000  0.00  0.00           P+0
HETATM   15  O   UNK     0       4.207   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.127   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.044  -2.739   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.009  -5.926   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      -0.342  -5.926   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.057  -9.663   0.000  0.00  0.00           O+0
HETATM   30  N   UNK     0      -2.778  -7.011   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.499  -4.358   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.088  -3.215   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       8.002   6.160   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       9.336  13.090   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      10.669  10.780   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
CONECT    1    2    6   44                                                  
CONECT    2    1    3   38                                                  
CONECT    3    2    4   34                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   33                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31                                                            
CONECT   33   24   19                                                       
CONECT   34    3   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    2   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44    1                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Value	Source
2-{[(2R,3S,4R,5S,6S)-2-({[({[(2S,3S,4R,5S)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoate	Generator

Chemical Formula

C₂₀H₂₉N₃O₁₉P₂

Average Mass

677.4020 Da

Monoisotopic Mass

677.08705 Da

IUPAC Name

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

Traditional Name

2-{[(2R,3S,4R,5S,6S)-2-[({[(2S,3S,4R,5S)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H]1[C@@H](O[P@](O)(=O)O[P@](O)(=O)OC[C@@H]2O[C@@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)O[C@@H](CO)[C@@H](O)[C@@H]1OC(=C)C(O)=O

InChI Identifier

InChI=1S/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/t9-,10-,12-,13+,14+,15+,16+,17-,19+/m0/s1

InChI Key

BEGZZYPUNCJHKP-FBZGRVJBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Escherichia coli	Bacteria	KNApSAcK

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-5-phosphate
Pentose phosphate
N-acyl-alpha-hexosamine
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Hydroxypyrimidine
Monoalkyl phosphate
Sugar acid
Pyrimidone
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Monosaccharide
Hydropyrimidine
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	-1.1	ALOGPS
logP	-4.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	326.71 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	133.31 m³·mol⁻¹	ChemAxon
Polarizability	56 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

Not Available

METLIN ID

Not Available

PubChem Compound

163071536

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine (NP0062860)

MOL for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

3D MOL for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

3D SDF for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

3D-SDF for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

PDB for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

3D PDB for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

SMILES for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

INCHI for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

Structure for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)

3D Structure for NP0062860 (UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine)