Marvin  09241213572D          

 44 46  0  0  1  0            999 V2000
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   15.0644   -6.7719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8575   -4.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7325   -4.8604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3035   -4.8603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575   -4.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5575   -5.6854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2075   -4.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2075   -4.8604    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.2075   -5.6854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3  7  1  0  0  0  0
  3  2  1  0  0  0  0
  7  5  1  0  0  0  0
  5  8  1  0  0  0  0
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  5  6  2  0  0  0  0
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  9  8  1  1  0  0  0
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 26 18  1  0  0  0  0
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 30 20  1  0  0  0  0
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 31 28  1  0  0  0  0
 28 30  1  0  0  0  0
 23 22  2  0  0  0  0
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 29 37  1  1  0  0  0
 30 33  1  6  0  0  0
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M  END
> <ID>
CHEBI:68507

> <NAME>
UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine

> <DEFINITION>
A UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine in which the anomeric centre of the glucosamine fragment has α-configuration.

> <STAR>
3

> <SYNONYM>
Uridine diphospho-N-acetylglucosamine enolpyruvate; UNAGEP; UdPGNAC-enolpyruvate; UDP-N-acetylglucosamine-enolpyruvate; UDP-N-acetylglucosamine-3-O-pyruvateether; UDP-N-acetylglucosamine-3-O-pyruvate ether; UDP-N-acetylglucosamine enolpyruvate; UDP-N-acetylenolpyruvylglucosamine; UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine; UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine; UDP-GlcNAc-pyruvate enol ether; EP-UDPGlCNAC; Enolpyruvyl-UDP-N-acetylglucosamine

> <IUPAC_NAME>
uridine 5'-{3-[2-acetamido-3-O-(1-carboxyethenyl)-2-deoxy-alpha-D-glucopyranosyl] dihydrogen diphosphate}

> <FORMULA>
C20H29N3O19P2

> <MASS>
677.40050

> <MONOISOTOPIC_MASS>
677.08705

> <CHARGE>
0

> <SMILES>
CC(=O)N[C@H]1[C@H](O[C@H](CO)[C@@H](O)[C@@H]1OC(=C)C(O)=O)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1ccc(=O)[nH]c1=O

> <INCHI>
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-/m1/s1

> <INCHIKEY>
BEGZZYPUNCJHKP-DBYWSUQTSA-N

> <CAS_REGISTRY_NUMBER>
70222-94-5

> <REAXYS_REGISTRY_NUMBER>
77170

> <CHEMIDPLUS>
70222-94-5

> <KEGG_COMPOUND_ACCESSION>
C04631

> <KNAPSACK_ACCESSION>
C00019554

> <METACYC_ACCESSION>
UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE

> <PDBECHEM_ACCESSION>
EPU

> <PUBMED_CITATION>
11284731; 22290954; 6222035; 7920261; 8448160; 9150408

$$$$