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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:90657565

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 1292.1206 Inferred 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 + β-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

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."


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
Page generated by SRI International Pathway Tools version 19.0 on Wed Jul 29, 2015, biocyc11.