Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 18:33:07 UTC
Update Date2020-05-11 17:45:54 UTC
HMDB IDHMDB0006229
Secondary Accession Numbers
  • HMDB06229
Metabolite Identification
Common Name5-Diphosphoinositol pentakisphosphate
Description5-Diphosphoinositol pentakisphosphate, also known as 5-PP-insp5 or 5beta-ip7, belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety. A myo-inositol pentakisphosphate that consists of 1D-myo-inositol having the five phospho groups located at positions 1, 2, 3, 4 and 6 as well as a diphospho group at position 5. 5-Diphosphoinositol pentakisphosphate is an extremely strong acidic compound (based on its pKa). 5-Diphosphoinositol pentakisphosphate exists in all eukaryotes, ranging from yeast to humans. Within humans, 5-diphosphoinositol pentakisphosphate participates in a number of enzymatic reactions. In particular, 5-diphosphoinositol pentakisphosphate can be biosynthesized from bisdiphosphoinositol tetrakisphosphate through its interaction with the enzyme diphosphoinositol polyphosphate phosphohydrolase 1. In addition, 5-diphosphoinositol pentakisphosphate can be converted into bisdiphosphoinositol tetrakisphosphate through the action of the enzyme inositol hexakisphosphate and diphosphoinositol-pentakisphosphate kinase 1. In humans, 5-diphosphoinositol pentakisphosphate is involved in inositol phosphate metabolism.
Structure
Data?1589219154
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
1D-Myo-inositol 5-diphosphoric acid 1,2,3,4,6-pentakisphosphoric acidGenerator
1D-Myo-inositol 5-diphosphoric acid pentakisphosphoric acidGenerator
5-Diphosphoinositol 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
1-O-Diphospho-D-myo-inositol pentakisphosphateHMDB
myo-Inositol 1,2,3,4,6-pentakis(dihydrogen phosphate) 5-(trihydrogen diphosphate)HMDB
Chemical FormulaC6H19O27P7
Average Molecular Weight740.0152
Monoisotopic Molecular Weight739.827700986
IUPAC Name{[(1R,2r,3S,4R,5s,6S)-2-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,2r,3S,4R,5s,6S)-2-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3,4,5,6-tetrakis(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry Number148077-18-3
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
Description belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056v-3500129000-92e02f48f80539fd2ebbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-2200039500-ca3324ec34611cb741e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-1100019100-a4bf41f87596bb42e4aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-3200592000-718743d53ee9b1a54936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-4100001900-58fc5d06ef574febc5fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9300013300-99dcc5e94c530a9c5eddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7891e87bda74c3a75d76Spectrum
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
FooDB IDFDB023849
KNApSAcK IDNot Available
Chemspider ID17216357
KEGG Compound IDC11526
BioCyc ID5-DIPHOSPHO-1D-MYO-INOSITOL-12346P
BiGG ID2265069
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDI7P
ChEBI ID30164
Food Biomarker OntologyNot Available
VMH IDPPMI12346P
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]

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