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Identification
YMDB IDYMDB00013
Name5-Diphosphoinositol pentakisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPC(18:4(6Z,9Z,12Z,15Z)/24:0) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(18:4(6Z,9Z,12Z,15Z)/24:0), in particular, consists of one 6Z,9Z,12Z,15Z-octadecatetraenoyl chain to the C-1 atom, and one tetracosanoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
Synonyms
  • (1R,2R,3S,4S,5R,6S)-2,3,4,5,6-Pentakis(phosphonooxy)cyclohexyl trihydrogen diphosphate
  • (1R,2R,3S,4S,5R,6S)-2,3,4,5,6-Pentakis(phosphonooxy)cyclohexyl trihydrogen diphosphoric acid
  • 1,2,3,4,6-pentakis-O-phosphono-1D-myo-inositol 5-(trihydrogen diphosphate)
  • 1D-myo-Inositol 5-diphosphate 1,2,3,4,6-pentakisphosphate
  • 1D-myo-inositol 5-diphosphate pentakisphosphate
  • 1D-myo-Inositol 5-diphosphoric acid 1,2,3,4,6-pentakisphosphoric acid
  • 1D-myo-Inositol 5-diphosphoric acid pentakisphosphoric acid
  • 5-Diphospho-1D-myo-inositol 1,2,3,4,6-pentakisphosphate
  • 5-diphospho-1D-myo-inositol pentakisphosphate
  • 5-Diphosphoinositol pentakisphosphoric acid
  • 5-PP-InsP5
  • 5beta 5PP-IP5
  • 5beta-IP7
  • diphosphoinositol pentakisphosphate
  • InsP7
  • IP7
  • PP-InsP5
  • Phosphatidylcholine(18:4/24:0)
  • Phosphatidylcholine(42:4)
  • PC(42:4)
  • GPCho(18:4/24:0)
  • Lecithin
  • 1-Stearidonoyl-2-lignoceroyl-sn-glycero-3-phosphocholine
  • PC(18:4/24:0)
  • 1-(6Z,9Z,12Z,15Z-Octadecatetraenoyl)-2-tetracosanoyl-sn-glycero-3-phosphocholine
  • GPCho(42:4)
CAS number149714-25-0
WeightAverage: 740.0152
Monoisotopic: 739.827700986
InChI KeyUPHPWXPNZIOZJL-KXXVROSKSA-N
InChIInChI=1S/C6H19O27P7/c7-34(8,9)27-1-2(28-35(10,11)12)4(30-37(16,17)18)6(32-40(25,26)33-39(22,23)24)5(31-38(19,20)21)3(1)29-36(13,14)15/h1-6H,(H,25,26)(H2,7,8,9)(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)(H2,19,20,21)(H2,22,23,24)/t1-,2+,3-,4-,5+,6+
IUPAC Name{[(1S,2R,3r,4S,5R,6s)-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-2,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional IUPAC Name5-PP-InsP5
Chemical FormulaC6H19O27P7
SMILES[H]OP(=O)(O[H])O[C@]1([H])[C@]([H])(OP(=O)(O[H])O[H])[C@@]([H])(OP(=O)(O[H])O[H])[C@]([H])(OP(=O)(O[H])OP(=O)(O[H])O[H])[C@@]([H])(OP(=O)(O[H])O[H])[C@]1([H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility14 g/LALOGPS
logP0.35ALOGPS
logP-4.9ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.14ChemAxon
Physiological Charge-12ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area447.09 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity111.89 m³·mol⁻¹ChemAxon
Polarizability46.86 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Inositol phosphate metabolismPW002495 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Inositol phosphate metabolismec00562 Map00562
SMPDB Reactions
5-Diphosphoinositol pentakisphosphate + Adenosine triphosphate1D-myo-inositol 1,5-bis(diphosphate) 2,3,4,6-tetrakisphosphate + ADP
5-Diphosphoinositol pentakisphosphate + Adenosine triphosphate3,5-bisdiphosphoinositol-1D-myo-inositol 2,3,4,6-tetrakisphosphate + ADP
5-Diphosphoinositol pentakisphosphate + Adenosine triphosphateMyo-Inositol hexakisphosphate + ADP + hydron
KEGG Reactions
5-Diphosphoinositol pentakisphosphate + waterMyo-Inositol hexakisphosphate + phosphate + hydron
Myo-Inositol hexakisphosphate + Adenosine triphosphate + hydron5-Diphosphoinositol pentakisphosphate + ADP
5-Diphosphoinositol pentakisphosphate + phosphate + hydron4,5-Bis(diphospho)-1D-myo-inositol tetrakisphosphate + water
5-Diphosphoinositol pentakisphosphate + phosphate + hydronwater + 5,6-Bis(diphospho)-1D-myo-inositol tetrakisphosphate
Myo-Inositol hexakisphosphate + phosphate + hydron5-Diphosphoinositol pentakisphosphate + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056v-3500129000-92e02f48f80539fd2ebbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-2200039500-ca3324ec34611cb741e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-1100019100-a4bf41f87596bb42e4aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-3200592000-718743d53ee9b1a54936JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-4100001900-58fc5d06ef574febc5fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9300013300-99dcc5e94c530a9c5eddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7891e87bda74c3a75d76JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Smolka, M. B., Albuquerque, C. P., Chen, S. H., Zhou, H. (2007). "Proteome-wide identification of in vivo targets of DNA damage checkpoint kinases." Proc Natl Acad Sci U S A 104:10364-10369.17563356
  • Mulugu, S., Bai, W., Fridy, P. C., Bastidas, R. J., Otto, J. C., Dollins, D. E., Haystead, T. A., Ribeiro, A. A., York, J. D. (2007). "A conserved family of enzymes that phosphorylate inositol hexakisphosphate." Science 316:106-109.17412958
  • Dubois, E., Scherens, B., Vierendeels, F., Ho, M. M., Messenguy, F., Shears, S. B. (2002). "In Saccharomyces cerevisiae, the inositol polyphosphate kinase activity of Kcs1p is required for resistance to salt stress, cell wall integrity, and vacuolar morphogenesis." J Biol Chem 277:23755-23763.11956213
  • Lee, Y. S., Mulugu, S., York, J. D., O'Shea, E. K. (2007). "Regulation of a cyclin-CDK-CDK inhibitor complex by inositol pyrophosphates." Science 316:109-112.17412959
  • Gruhler, A., Olsen, J. V., Mohammed, S., Mortensen, P., Faergeman, N. J., Mann, M., Jensen, O. N. (2005). "Quantitative phosphoproteomics applied to the yeast pheromone signaling pathway." Mol Cell Proteomics 4:310-327.15665377
  • Albuquerque, C. P., Smolka, M. B., Payne, S. H., Bafna, V., Eng, J., Zhou, H. (2008). "A multidimensional chromatography technology for in-depth phosphoproteome analysis." Mol Cell Proteomics 7:1389-1396.18407956
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
  • Safrany, S. T., Ingram, S. W., Cartwright, J. L., Falck, J. R., McLennan, A. G., Barnes, L. D., Shears, S. B. (1999). "The diadenosine hexaphosphate hydrolases from Schizosaccharomyces pombe and Saccharomyces cerevisiae are homologues of the human diphosphoinositol polyphosphate phosphohydrolase. Overlapping substrate specificities in a MutT-type protein." J Biol Chem 274:21735-21740.10419486
  • Li, X., Gerber, S. A., Rudner, A. D., Beausoleil, S. A., Haas, W., Villen, J., Elias, J. E., Gygi, S. P. (2007). "Large-scale phosphorylation analysis of alpha-factor-arrested Saccharomyces cerevisiae." J Proteome Res 6:1190-1197.17330950
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID30164
HMDB IDHMDB06229
Pubchem Compound ID443247
Kegg IDC11526
ChemSpider ID23107121
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc ID5-DIPHOSPHO-1D-MYO-INOSITOL-12346P

Enzymes

General function:
Involved in inositol trisphosphate 3-kinase activity
Specific function:
Has kinase activity and phosphorylates inositol-1,4,5- trisphosphate (Ins(1,4,5)P3) and inositol-1,3,4,5- tetrakisphosphate (Ins(1,3,4,5)P4). Has low kinase activity towards InsP6. Originally it was proposed that the ARGRI and ARGRIII proteins are more likely to be involved in the control of ARGRII activity
Gene Name:
ARG82
Uniprot ID:
P07250
Molecular weight:
40352.5
Reactions
ATP + 1D-myo-inositol 1,4,5-trisphosphate → ADP + 1D-myo-inositol 1,4,5,6-tetrakisphosphate.
ATP + 1D-myo-inositol 1,4,5,6-tetrakisphosphate → ADP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate.
General function:
Involved in hydrolase activity
Specific function:
May eliminate potentially toxic dinucleoside polyphosphates during sporulation. Most active against diadenosine 5',5'''-P1,P6-hexaphosphate (Ap6A). Can also hydrolyze diadenosine 5',5'''-P1,P5-pentaphosphate (Ap5A), adenosine 5'-pentaphosphate, and adenosine 5'-tetraphosphate are also substrates, but not diadenosine 5',5'''-P1,P4-tetraphosphate (Ap4A) or other dinucleotides, mononucleotides, nucleotide sugars, or nucleotide alcohols. Also cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate) and [PP]2-InsP4 (bisdiphosphoinositol tetrakisphosphate)
Gene Name:
DDP1
Uniprot ID:
Q99321
Molecular weight:
21572.30078
Reactions
Diphospho-myo-inositol polyphosphate + H(2)O → myo-inositol polyphosphate + phosphate.
General function:
Involved in inositol trisphosphate 3-kinase activity
Specific function:
Converts inositol hexakisphosphate (InsP6) to diphosphoinositol pentakisphosphate (InsP7/PP-InsP5). Involved in phosphate regulation and polyphosphate accumulation. Required for resistance to salt stress, cell wall integrity, vacuole morphogenesis, and telomere maintenance
Gene Name:
KCS1
Uniprot ID:
Q12494
Molecular weight:
119549.0
Reactions
ATP + 1D-myo-inositol hexakisphosphate → ADP + 5-diphospho-1D-myo-inositol (1,2,3,4,6)pentakisphosphate.
ATP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate → ADP + diphospho-1D-myo-inositol tetrakisphosphate (isomeric configuration unknown).
General function:
Involved in acid phosphatase activity
Specific function:
Bifunctional inositol kinase that catalyzes the formation of diphosphoinositol pentakisphosphate (InsP7 or PP- InsP5) and bi-diphosphoinositol tetrakisphosphate (InsP8 or PP2- InsP4). Converts inositolitol hexakisphosphate (InsP6) to InsP7. Also able to convert InsP7 to InsP8. Probably specifically mediates the formation of 4PP-InsP5 and 6PP-InsP5 InsP7 isomers but not of 5PP-IP5 InsP7 isomer. Required for maintaining celllular integrity, normal growth and interactions with the ARP complex. Acts as a regulator of the PHO80-PHO85 cyclin/cyclin-dependent kinase (CDK) complex, thereby regulating signaling of phosphate availability. Required for the function of the cortical actin cytoskeleton, possibly by participating in correct F-actin localization and ensuring polarized growth
Gene Name:
VIP1
Uniprot ID:
Q06685
Molecular weight:
129754.0
Reactions
ATP + 1D-myo-inositol hexakisphosphate → ADP + 5-diphospho-1D-myo-inositol (1,2,3,4,6)pentakisphosphate.
ATP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate → ADP + diphospho-1D-myo-inositol tetrakisphosphate (isomeric configuration unknown).
ATP + 1D-myo-inositol 5-diphosphate pentakisphosphate → ADP + 1D-myo-inositol bisdiphosphate tetrakisphosphate (isomeric configuration unknown).
General function:
Involved in ATP binding
Specific function:
Has kinase activity and phosphorylates inositol- 1,3,4,5,6-pentakisphosphate (Ins(1,3,4,5,6)P5) to produce 1,2,3,4,5,6-hexakisphosphate (InsP6), also known as phytate
Gene Name:
IPK1
Uniprot ID:
Q06667
Molecular weight:
32917.69922
Reactions
ATP + 1D-myo-inositol 1,3,4,5,6-pentakisphosphate → ADP + 1D-myo-inositol hexakisphosphate.