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Showing metabocard for D-myo-Inositol 1,4-bisphosphate (HMDB0000968)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-11-08 15:33:02 UTC
HMDB IDHMDB0000968
Secondary Accession Numbers
  • HMDB0062568
  • HMDB00968
  • HMDB62568
Metabolite Identification
Common NameD-myo-Inositol 1,4-bisphosphate
DescriptionD-myo-Inositol 1,4-bisphosphate 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. D-myo-Inositol 1,4-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-myo-Inositol 1,4-bisphosphate is a substrate for several proteins including inositol polyphosphate 1-phosphatase, phosphatidylinositol 4,5-bisphosphate 5-phosphatase A, skeletal muscle and kidney enriched inositol phosphatase, and type I inositol-1,4,5-trisphosphate 5-phosphatase.
Structure
Data?1573152054
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
D-Myo-inositol 1,4-bisphosphateChEBI
D-MYO-inositol-1,4-bisphosphATEChEBI
Inositol 1,4-bisphosphateChEBI
Myo-inositol 1,4-bisphosphateChEBI
D-Myo-inositol 1,4-bisphosphoric acidGenerator
D-MYO-inositol-1,4-bisphosphoric acidGenerator
Inositol 1,4-bisphosphoric acidGenerator
Myo-inositol 1,4-bisphosphoric acidGenerator
1D-Myo-inositol 1,4-bisphosphoric acidGenerator
Chemical FormulaC6H14O12P2
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
IUPAC Name{[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry Number74465-19-3
SMILES
O[C@H]1[C@@H](O)[C@@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1OP(O)(O)=O
InChI Identifier
InChI=1S/C6H14O12P2/c7-1-2(8)6(18-20(14,15)16)4(10)3(9)5(1)17-19(11,12)13/h1-10H,(H2,11,12,13)(H2,14,15,16)/t1-,2-,3-,4+,5+,6+/m1/s1
InChI KeyPELZSPZCXGTUMR-RTPHHQFDSA-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
  • Monoalkyl phosphate
  • Cyclohexanol
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility24.4 g/LALOGPS
logP-1.3ALOGPS
logP-4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)0.86ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area214.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.52 m³·mol⁻¹ChemAxon
Polarizability25.1 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, Positivesplash10-0002-9321000000-9f623a36e7cbbf411892JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-03dj-9163026000-1848e4d3af73c15a6fe2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2039000000-30867310a54aeefc9f07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2029000000-09a80b30252576945f03JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-8920000000-da85c9dd4243595988ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-4009000000-0bfc6eac93cb1d6f5150JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9012000000-52b4d66a2cc414f3c15fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-188d2aa04460c53bd120JSpectraViewer
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 IDDB03158
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022343
KNApSAcK IDC00007484
Chemspider ID17216032
KEGG Compound IDC01220
BioCyc IDNot Available
BiGG ID37109
Wikipedia LinkNot Available
METLIN ID5911
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17816
Food Biomarker OntologyNot Available
VMH IDMI14P
References
Synthesis ReferenceAuchus, Richard J.; Kaiser, Susan L.; Majerus, Philip W. Synthesis of inositol 1,2-(cyclic)-4,5-trisphosphate. Proceedings of the National Academy of Sciences of the United States of America (1987), 84(5), 1206-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Spiegelberg BD, Xiong JP, Smith JJ, Gu RF, York JD: Cloning and characterization of a mammalian lithium-sensitive bisphosphate 3'-nucleotidase inhibited by inositol 1,4-bisphosphate. J Biol Chem. 1999 May 7;274(19):13619-28. [PubMed:10224133 ]
  2. Eberhard M, Erne P: Inositol 1,4,5-trisphosphate-induced calcium release in permeabilized platelets is coupled to hydrolysis of inositol 1,4,5-trisphosphate to inositol 1,4-bisphosphate. Biochem Biophys Res Commun. 1993 Aug 31;195(1):19-24. [PubMed:8363599 ]
  3. Eberhard M, Erne P: Regulation of inositol 1,4,5-trisphosphate-induced calcium release by inositol 1,4,5-trisphosphate and calcium in human platelets. J Recept Signal Transduct Res. 1995 Jan-Mar;15(1-4):297-309. [PubMed:8903946 ]

Enzymes

Enzyme Details
1. Type I inositol 1,4,5-trisphosphate 5-phosphatase
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Major isoenzyme hydrolyzing the calcium-mobilizing second messenger Ins(1,4,5)P3, this is a signal-terminating reaction.
Gene Name:
INPP5A
Uniprot ID:
Q14642
Molecular weight:
47819.155
Reactions
Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
Enzyme Details
2. Inositol polyphosphate 1-phosphatase
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Not Available
Gene Name:
INPP1
Uniprot ID:
P49441
Molecular weight:
43997.62
Reactions
D-myo-Inositol 1,4-bisphosphate + Water → D-myo-Inositol 4-phosphate + Phosphatedetails
Enzyme Details
3. Phosphatidylinositol 4,5-bisphosphate 5-phosphatase A
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Inositol 5-phosphatase, which converts inositol 1,4,5-trisphosphate to inositol 1,4-bisphosphate. Also converts phosphatidylinositol 4,5-bisphosphate to phosphatidylinositol 4-phosphate and inositol 1,3,4,5-tetrakisphosphate to inositol 1,3,4-trisphosphate in vitro. May be involved in modulation of the function of inositol and phosphatidylinositol polyphosphate-binding proteins that are present at membranes ruffles (By similarity).
Gene Name:
INPP5J
Uniprot ID:
Q15735
Molecular weight:
70238.575
Reactions
Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
Enzyme Details
4. Inositol polyphosphate 5-phosphatase K
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Inositol 5-phosphatase which acts on inositol 1,4,5-trisphosphate, inositol 1,3,4,5-tetrakisphosphate, phosphatidylinositol 4,5-bisphosphate and phosphatidylinositol 3,4,5-trisphosphate. Has 6-fold higher affinity for phosphatidylinositol 4,5-bisphosphate than for inositol 1,4,5-trisphosphate. May negatively regulate assembly of the actin cytoskeleton.
Gene Name:
INPP5K
Uniprot ID:
Q9BT40
Molecular weight:
42783.425
Reactions
Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
Inositol 1,4,5-trisphosphate + Water → D-myo-Inositol 1,4-bisphosphate + Phosphatedetails
Enzyme Details
5. Glycophorin-B
General function:
Not Available
Specific function:
This protein is a minor sialoglycoprotein in erythrocyte membranes
Gene Name:
GYPB
Uniprot ID:
P06028
Molecular weight:
9795.6
Enzyme Details
6. Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Phosphatidylinositol (PtdIns) phosphatase that specifically hydrolyzes the 5-phosphate of phosphatidylinositol-3,4,5-trisphosphate (PtdIns(3,4,5)P3) to produce PtdIns(3,4)P2, thereby negatively regulating the PI3K (phosphoinositide 3-kinase) pathways. Plays a central role in regulation of PI3K-dependent insulin signaling, although the precise molecular mechanisms and signaling pathways remain unclear. While overexpression reduces both insulin-stimulated MAP kinase and Akt activation, its absence does not affect insulin signaling or GLUT4 trafficking. Confers resistance to dietary obesity. May act by regulating AKT2, but not AKT1, phosphorylation at the plasma membrane. Part of a signaling pathway that regulates actin cytoskeleton remodeling. Required for the maintenance and dynamic remodeling of actin structures as well as in endocytosis, having a major impact on ligand-induced EGFR internalization and degradation. Participates in regulation of cortical and submembraneous actin by hydrolyzing PtdIns(3,4,5)P3 thereby regulating membrane ruffling. Regulates cell adhesion and cell spreading. Required for HGF-mediated lamellipodium formation, cell scattering and spreading. Acts as a negative regulator of EPHA2 receptor endocytosis by inhibiting via PI3K-dependent Rac1 activation. Acts as a regulator of neuritogenesis by regulating PtdIns(3,4,5)P3 level and is required to form an initial protrusive pattern, and later, maintain proper neurite outgrowth. Acts as a negative regulator of the FC-gamma-RIIA receptor (FCGR2A). Mediates signaling from the FC-gamma-RIIB receptor (FCGR2B), playing a central role in terminating signal transduction from activating immune/hematopoietic cell receptor systems. Involved in EGF signaling pathway. Upon stimulation by EGF, it is recruited by EGFR and dephosphorylates PtdIns(3,4,5)P3. Plays a negative role in regulating the PI3K-PKB pathway, possibly by inhibiting PKB activity. Down-regulates Fc-gamma-R-mediated phagocytosis in macrophages independently of INPP5D/SHIP1. In macrophages, down-regulates NF-kappa-B-dependent gene transcription by regulating macrophage colony-stimulating factor (M-CSF)-induced signaling. May also hydrolyze PtdIns(1,3,4,5)P4, and could thus affect the levels of the higher inositol polyphosphates like InsP6.
Gene Name:
INPPL1
Uniprot ID:
O15357
Molecular weight:
138597.495