heptadecaprenyl diphosphate (YMDB00643)

Identification
YMDB IDYMDB00643
Nameheptadecaprenyl diphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionheptadecaprenyl diphosphate belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety. heptadecaprenyl diphosphate is a moderately acidic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (E)-heptaprenyl diphosphate
  • all-trans-Heptaprenyl diphosphate
  • Heptadecaprenyl diphosphoric acid
CAS numberNot Available
WeightAverage: 1335.9644
Monoisotopic: 1335.007429858
InChI KeyULBHNJNYJOQJSB-HFWURXGYSA-N
InChIInChI=1S/C85H140O7P2/c1-69(2)35-19-36-70(3)37-20-38-71(4)39-21-40-72(5)41-22-42-73(6)43-23-44-74(7)45-24-46-75(8)47-25-48-76(9)49-26-50-77(10)51-27-52-78(11)53-28-54-79(12)55-29-56-80(13)57-30-58-81(14)59-31-60-82(15)61-32-62-83(16)63-33-64-84(17)65-34-66-85(18)67-68-91-94(89,90)92-93(86,87)88/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,65,67H,19-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64,66,68H2,1-18H3,(H,89,90)(H2,86,87,88)/b70-37+,71-39+,72-41+,73-43+,74-45+,75-47+,76-49+,77-51+,78-53+,79-55+,80-57+,81-59+,82-61+,83-63+,84-65+,85-67+
IUPAC Name({[(3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67-heptadecamethyloctahexaconta-2,6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66-heptadecaen-1-yl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Nameheptadecaprenyl diphosphate
Chemical FormulaC85H140O7P2
SMILES[H]C(CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])CCC(C)=C([H])COP(O)(=O)OP(O)(O)=O)=C(C)CCC=C(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentBactoprenol diphosphates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl diphosphate
  • Polyprenyl monophosphate
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00052 g/LALOGPS
logP9.98ALOGPS
logP26.85ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count53ChemAxon
Refractivity429.97 m³·mol⁻¹ChemAxon
Polarizability172.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • lipid particle
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
hexadecaprenyl diphosphate + Isopentenyl pyrophosphate ↔ Pyrophosphate + heptadecaprenyl diphosphate
heptadecaprenyl diphosphate + Isopentenyl pyrophosphate ↔ Pyrophosphate + octadecaprenyl diphosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0954000000-7b64e8edf67c8918885dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1910000000-97b1247ecd92ddd27ba7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1901120000-0966c7ccbb0f78b612dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0409000000-ea52efe7399fc5f6aabcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-7901000000-886e24b2b860540e345fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6203ca9514f17eebbfb7JSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Sato, M., Sato, K., Nishikawa, S., Hirata, A., Kato, J., Nakano, A. (1999). "The yeast RER2 gene, identified by endoplasmic reticulum protein localization mutations, encodes cis-prenyltransferase, a key enzyme in dolichol synthesis." Mol Cell Biol 19:471-483.9858571
  • Grabinska, K., Palamarczyk, G. (2002). "Dolichol biosynthesis in the yeast Saccharomyces cerevisiae: an insight into the regulatory role of farnesyl diphosphate synthase." FEMS Yeast Res 2:259-265.12702274
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID53036
HMDB IDNot Available
Pubchem Compound ID74956401
Kegg IDNot Available
ChemSpider ID23107114
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Putative dehydrodolichyl diphosphate synthase
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Could be a cis-prenyl transferase that adds multiple copies of isopentenyl pyrophosphate (ipp) to farnesyl pyrophosphate (FPP) to produce dehydrodolichyl diphosphate (DeDol- PP)
Gene Name:
SRT1
Uniprot ID:
Q03175
Molecular weight:
40199.69922
Reactions
Protein Details
2. Dehydrodolichyl diphosphate synthase
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Cis-prenyl transferase that adds multiple copies of isopentenyl pyrophosphate (IPP) to farnesyl pyrophosphate (FPP) to produce dehydrodolichyl diphosphate (Dedol-PP)
Gene Name:
RER2
Uniprot ID:
P35196
Molecular weight:
32693.30078
Reactions