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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 18:33:07 UTC
Update Date2019-01-11 19:19:09 UTC
HMDB IDHMDB0006229
Secondary Accession Numbers
  • HMDB06229
Metabolite Identification
Common Name5-Diphosphoinositol pentakisphosphate
DescriptionDiphosphoinositol pentakisphosphate (InsP7) contains an inositol polyphosphate that contains a pyrophosphate bond. InsP7 is formed from inositol hexakisphosphate (InsP6) by a family of three inositol hexakisphosphate kinases (InsP6K). (PMID: 15533939 ). It is an intracellular signaling molecule that regulates many cellular processes including endocytosis, vesicle trafficking, apoptosis, and DNA repair. (PMID 15316027 ).
Structure
Data?1547234349
Synonyms
ValueSource
(1R,2R,3S,4S,5R,6S)-2,3,4,5,6-Pentakis(phosphonooxy)cyclohexyl trihydrogen diphosphateChEBI
1D-myo-Inositol 5-diphosphate 1,2,3,4,6-pentakisphosphateChEBI
1D-myo-Inositol 5-diphosphate pentakisphosphateChEBI
5-PP-InsP5ChEBI
(1R,2R,3S,4S,5R,6S)-2,3,4,5,6-Pentakis(phosphonooxy)cyclohexyl trihydrogen diphosphoric acidGenerator
5-Diphosphoinositol pentakisphosphoric acidGenerator
1D-myo-Inositol 5-diphosphoric acid 1,2,3,4,6-pentakisphosphoric acidGenerator
1D-myo-Inositol 5-diphosphoric acid pentakisphosphoric acidGenerator
1,2,3,4,6-Pentakis-O-phosphono-1D-myo-inositol 5-(trihydrogen diphosphate)HMDB
5-diphospho-1D-myo-Inositol 1,2,3,4,6-pentakisphosphateHMDB
5-diphospho-1D-myo-Inositol pentakisphosphateHMDB
5beta 5pp-IP5HMDB
5beta-IP7HMDB
Diphosphoinositol pentakisphosphateHMDB
InsP7HMDB
IP7HMDB
PP-InsP5HMDB
Chemical FormulaC6H19O27P7
Average Molecular Weight740.0152
Monoisotopic Molecular Weight739.827700986
IUPAC Name{[(1S,2R,3r,4S,5R,6s)-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-2,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name5-PP-InsP5
CAS Registry NumberNot Available
SMILES
OP(O)(=O)O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(=O)OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O
InChI Identifier
InChI=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+
InChI KeyUPHPWXPNZIOZJL-KXXVROSKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as inositol phosphates. These are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056v-3500129000-92e02f48f80539fd2ebbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-2200039500-ca3324ec34611cb741e8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-1100019100-a4bf41f87596bb42e4aaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-3200592000-718743d53ee9b1a54936JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-4100001900-58fc5d06ef574febc5fcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9300013300-99dcc5e94c530a9c5eddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7891e87bda74c3a75d76JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023849
KNApSAcK IDNot Available
Chemspider ID17216357
KEGG Compound IDC11526
BioCyc IDNot Available
BiGG ID2265069
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDI7P
ChEBI ID30164
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pesesse X, Choi K, Zhang T, Shears SB: Signaling by higher inositol polyphosphates. Synthesis of bisdiphosphoinositol tetrakisphosphate ("InsP8") is selectively activated by hyperosmotic stress. J Biol Chem. 2004 Oct 15;279(42):43378-81. Epub 2004 Aug 16. [PubMed:15316027 ]
  2. Nagata E, Luo HR, Saiardi A, Bae BI, Suzuki N, Snyder SH: Inositol hexakisphosphate kinase-2, a physiologic mediator of cell death. J Biol Chem. 2005 Jan 14;280(2):1634-40. Epub 2004 Nov 8. [PubMed:15533939 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate), suggesting that it may play a role in signal transduction. Also able to catalyze the hydrolysis of dinucleoside oligophosphates, with Ap6A and Ap5A being the preferred substrates. The major reaction products are ADP and p4a from Ap6A and ADP and ATP from Ap5A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT11
Uniprot ID:
Q96G61
Molecular weight:
18558.835
General function:
Involved in hydrolase activity
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate) and [PP]2-InsP4 (bisdiphosphoinositol tetrakisphosphate), suggesting that it may play a role in signal transduction. InsP6 (inositol hexakisphophate) is not a substrate. Acts as a negative regulator of the ERK1/2 pathway. Also able to catalyze the hydrolysis of dinucleoside oligophosphates, with Ap6A and Ap5A being the preferred substrates. The major reaction products are ADP and p4a from Ap6A and ADP and ATP from Ap5A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT3
Uniprot ID:
O95989
Molecular weight:
19470.855
General function:
Involved in hydrolase activity
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate), PP-InsP4 and [PP]2-InsP4 (bisdiphosphoinositol tetrakisphosphate), suggesting that it may play a role in signal transduction. Also able to catalyze the hydrolysis of dinucleoside oligophosphate Ap6A, but not Ap5A. The major reaction products are ADP and p4a from Ap6A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT4
Uniprot ID:
Q9NZJ9
Molecular weight:
20305.895
General function:
Not Available
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. Activated when cells are exposed to hyperosmotic stress.
Gene Name:
PPIP5K1
Uniprot ID:
Q6PFW1
Molecular weight:
159519.82
Reactions
Adenosine triphosphate + 5-Diphosphoinositol pentakisphosphate → ADP + 1D-myo-Inositol bisdiphosphate tetrakisphosphatedetails
General function:
Not Available
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.
Gene Name:
PPIP5K2
Uniprot ID:
O43314
Molecular weight:
138104.925
Reactions
Adenosine triphosphate + 5-Diphosphoinositol pentakisphosphate → ADP + 1D-myo-Inositol bisdiphosphate tetrakisphosphatedetails