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MetaCyc Compound: C70 dolichol phosphate

Synonyms: dolichol-14 phosphate

Superclasses: a dolichyl phosphate

Citations: [Jadid11]

Chemical Formula: C70H115O4P

Molecular Weight: 1051.6 Daltons

Monoisotopic Molecular Weight: 1052.8689487541 Daltons

C70 dolichol phosphate compound structure

SMILES: CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(CCOP(=O)([O-])[O-])C

InChI: InChI=1S/C70H117O4P/c1-57(2)29-16-30-58(3)31-17-32-59(4)33-18-34-60(5)35-19-36-61(6)37-20-38-62(7)39-21-40-63(8)41-22-42-64(9)43-23-44-65(10)45-24-46-66(11)47-25-48-67(12)49-26-50-68(13)51-27-52-69(14)53-28-54-70(15)55-56-74-75(71,72)73/h29,31,33,35,37,39,41,43,45,47,49,51,53,70H,16-28,30,32,34,36,38,40,42,44,46,48,50,52,54-56H2,1-15H3,(H2,71,72,73)/p-2/b58-31+,59-33+,60-35-,61-37-,62-39-,63-41-,64-43-,65-45-,66-47-,67-49-,68-51-,69-53-

InChIKey: InChIKey=HEEYBOURDAHIRM-YEPMOUTASA-L

Unification Links: PubChem:91819910

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 1292.1206Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

protein N-glycosylation (eukaryotic, high mannose) :
a dolichyl phosphate + GDP-α-D-mannose → a dolichyl β-D-mannosyl phosphate + GDP
a dolichyl phosphate + UDP-N-acetyl-α-D-glucosamine → an N-acetyl-α-D-glucosaminyl-diphosphodolichol + UMP
a dolichyl phosphate + UDP-α-D-glucose → a dolichyl β-D-glucosyl phosphate + UDP

Not in pathways:
a dolichyl phosphate + H2O → a dolichol + phosphate

Reactions known to produce the compound:

dolichol and dolichyl phosphate biosynthesis :
a dolichol + CTP → a dolichyl phosphate + CDP + H+

protein N-glycosylation (eukaryotic, high mannose) :
a (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-glucosyl phosphate[rough endoplasmic reticulum lumen] → a (glucosyl)3(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-glucosyl phosphate[rough endoplasmic reticulum lumen] → a (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-glucosyl phosphate[rough endoplasmic reticulum lumen] → a glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-mannosyl phosphate[rough endoplasmic reticulum lumen] → a (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-mannosyl phosphate[rough endoplasmic reticulum lumen] → a (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-mannosyl phosphate[rough endoplasmic reticulum lumen] → a (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-mannosyl phosphate[rough endoplasmic reticulum lumen] → a (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]

Not in pathways:
a dolichyl β-D-glucosyl phosphate + H2O → a dolichyl phosphate + D-glucopyranose + H+
a dolichyl β-D-mannosyl phosphate + H2O → a dolichyl phosphate + D-mannose + H+

In Reactions of unknown directionality:

Not in pathways:
a dolichyl phosphate + UDP-α-D-xylose = dolichyl D-xylosyl phosphate + UDP
a dolichyl phosphate + UDP-N-acetyl-α-D-glucosamine = a dolichyl N-acetyl-α-D-glucosaminyl phosphate + UDP
a (glucosyl)3(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + H2O = a dolichyl phosphate + (glucosyl)3-(mannosyl)9-(N-acetylglucosaminyl)2-phosphate + 2 H+
dolichyl D-xylosyl phosphate + a core protein L-serine = a dolichyl phosphate + O-β-D-xylosyl-[core protein] + H+
a dolichyl β-D-mannosyl phosphate + a [protein]-(L-serine/L-threonine) = a dolichyl phosphate + a [protein]-O-D-mannosyl-(L-serine/L-threonine) + H+
a dolichyl diphosphate + (polyphosphate)(n) = a dolichyl phosphate + (polyphosphate)(n+1)
a dolichyl diphosphate + H2O = a dolichyl phosphate + phosphate + H+

Credits:
Created 08-Sep-2011 by Dreher KA, PMN


References

Burda99: Burda P, Aebi M (1999). "The dolichol pathway of N-linked glycosylation." Biochim Biophys Acta 1426(2);239-57. PMID: 9878760

Jadid11: Jadid N, Mialoundama AS, Heintz D, Ayoub D, Erhardt M, Mutterer J, Meyer D, Alioua A, Van Dorsselaer A, Rahier A, Camara B, Bouvier F (2011). "DOLICHOL PHOSPHATE MANNOSE SYNTHASE1 mediates the biogenesis of isoprenyl-linked glycans and influences development, stress response, and ammonium hypersensitivity in Arabidopsis." Plant Cell 23(5);1985-2005. PMID: 21558543

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Sato01: Sato M, Fujisaki S, Sato K, Nishimura Y, Nakano A (2001). "Yeast Saccharomyces cerevisiae has two cis-prenyltransferases with different properties and localizations. Implication for their distinct physiological roles in dolichol synthesis." Genes Cells 6(6);495-506. PMID: 11442630


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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