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Record Information
Version3.6
Creation Date2006-05-22 15:12:24 UTC
Update Date2016-08-17 21:43:37 UTC
HMDB IDHMDB02985
Secondary Accession NumbersNone
Metabolite Identification
Common NameInositol phosphate
DescriptionInositol phosphate is an intermediate step in the metabolism of glucose-6-phosphate to myo-inositol. myo-Inositol is synthesized from glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerised by INYNA1 to myo-inositol 1-phosphate, which is then dephosphorylated by IMPA1 to give myo-inositol.
Structure
Thumb
Synonyms
ValueSource
D-myo-Inositol (6)-monophosphateChEBI
D-myo-Inositol (6)-phosphateChEBI
I6PChEBI
Ins(6)PChEBI
Ins6pChEBI
D-myo-Inositol (6)-monophosphoric acidGenerator
1D-myo-Inositol 6-phosphoric acidGenerator
D-myo-Inositol (6)-phosphoric acidGenerator
1D-myo-Inositol 1-monophosphateHMDB
1D-myo-Inositol 1-phosphateHMDB
D-myo-Inositol-1-phosphateHMDB
Inositol 1-monophosphateHMDB
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(1R,2R,3R,4R,5R,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,2R,3R,4R,5R,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphonic acid
CAS Registry Number15421-51-9
SMILES
O[C@@H]1[C@@H](O)[C@H](O)[C@@H](OP(O)(O)=O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H13O9P/c7-1-2(8)4(10)6(5(11)3(1)9)15-16(12,13)14/h1-11H,(H2,12,13,14)/t1-,2-,3-,4+,5-,6-/m1/s1
InChI KeyInChIKey=INAPMGSXUVUWAF-XCMZKKERSA-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 ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Monoalkyl phosphate
  • Cyclohexanol
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Inositol phosphate metabolism
  • Component of Streptomycin biosynthesis
ApplicationNot Available
Cellular locations
  • Nucleus
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 Solubility39.5 mg/mLALOGPS
logP-2ALOGPS
logP-3.9ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area167.91 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.65 m3·mol-1ChemAxon
Polarizability20.53 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Nucleus
Biofluid Locations
  • Feces
  • Prostate Tissue
Tissue Location
  • Bladder
  • Brain
  • Kidney
  • Muscle
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Not AvailableNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Prostate TissueDetected and Quantified0.5 (0.0-1.0) umol/g tissueAdult (>18 years old)Both
Prostate Cancer
details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023090
KNApSAcK IDNot Available
Chemspider ID10465039
KEGG Compound IDC01177
BioCyc IDCPD-180
BiGG ID1484840
Wikipedia LinkInositol phosphate
NuGOwiki LinkHMDB02985
Metagene LinkHMDB02985
METLIN ID359
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18297
References
Synthesis ReferencePirrung, Michael C. Discovery of a catalytic asymmetric phosphorylation through selection of a minimal kinase mimic: A concise total synthesis of D-myo-inositol-1-phosphate. Chemtracts (2001), 14(14), 802-804.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  2. Jooste EH, Sharma A, Zhang Y, Emala CW: Rapacuronium augments acetylcholine-induced bronchoconstriction via positive allosteric interactions at the M3 muscarinic receptor. Anesthesiology. 2005 Dec;103(6):1195-203. [16306732 ]
  3. Buccellati C, Sala A, Rossoni G, Capra V, Rovati GE, Di Gennaro A, Folco G, Colli S, Casagrande C: Pharmacological characterization of 2NTX-99 [4-methoxy-N1-(4-trans-nitrooxycyclohexyl)-N3-(3-pyridinylmethyl)-1,3-benz enedicarboxamide], a potential antiatherothrombotic agent with antithromboxane and nitric oxide donor activity in platelet and vascular preparations. J Pharmacol Exp Ther. 2006 May;317(2):830-7. Epub 2006 Jan 6. [16399881 ]
  4. Honchar MP, Olney JW, Sherman WR: Systemic cholinergic agents induce seizures and brain damage in lithium-treated rats. Science. 1983 Apr 15;220(4594):323-5. [6301005 ]
  5. Grimminger F, Rose F, Sibelius U, Meinhardt M, Potzsch B, Spriestersbach R, Bhakdi S, Suttorp N, Seeger W: Human endothelial cell activation and mediator release in response to the bacterial exotoxins Escherichia coli hemolysin and staphylococcal alpha-toxin. J Immunol. 1997 Aug 15;159(4):1909-16. [9257856 ]
  6. Kato T, Shioiri T, Takahashi S, Inubushi T: Measurement of brain phosphoinositide metabolism in bipolar patients using in vivo 31P-MRS. J Affect Disord. 1991 Aug;22(4):185-90. [1658103 ]
  7. Waldo GL, Corbitt J, Boyer JL, Ravi G, Kim HS, Ji XD, Lacy J, Jacobson KA, Harden TK: Quantitation of the P2Y(1) receptor with a high affinity radiolabeled antagonist. Mol Pharmacol. 2002 Nov;62(5):1249-57. [12391289 ]
  8. King WG, Rittenhouse SE: Inhibition of protein kinase C by staurosporine promotes elevated accumulations of inositol trisphosphates and tetrakisphosphate in human platelets exposed to thrombin. J Biol Chem. 1989 Apr 15;264(11):6070-4. [2703480 ]
  9. Chen WY, Ko FN, Lin CN, Teng CM: The effect of 3-[2-(cyclopropylamino)ethoxy]xanthone on platelet thromboxane formation. Thromb Res. 1994 Jul 1;75(1):81-90. [8073410 ]
  10. Siess W: Evidence for the formation of inositol 4-monophosphate in stimulated human platelets. FEBS Lett. 1985 Jun 3;185(1):151-6. [3996593 ]
  11. Fourcade O, Simon MF, Litt L, Samii K, Chap H: Propofol inhibits human platelet aggregation induced by proinflammatory lipid mediators. Anesth Analg. 2004 Aug;99(2):393-8, table of contents. [15271713 ]
  12. Ishii H, Umeda F, Hashimoto T, Nawata H: Increased inositol phosphate accumulation in platelets from patients with NIDDM. Diabetes Res Clin Pract. 1991 Oct;14(1):21-7. [1660805 ]
  13. Bae YS, Cantley LG, Chen CS, Kim SR, Kwon KS, Rhee SG: Activation of phospholipase C-gamma by phosphatidylinositol 3,4,5-trisphosphate. J Biol Chem. 1998 Feb 20;273(8):4465-9. [9468499 ]
  14. Williams RS: Pharmacogenetics in model systems: defining a common mechanism of action for mood stabilisers. Prog Neuropsychopharmacol Biol Psychiatry. 2005 Jul;29(6):1029-37. [15950352 ]
  15. Ross TS, Majerus PW: Inositol-1,2-cyclic-phosphate 2-inositolphosphohydrolase. Substrate specificity and regulation of activity by phospholipids, metal ion chelators, and inositol 2-phosphate. J Biol Chem. 1991 Jan 15;266(2):851-6. [1845995 ]
  16. Kories C, Czyborra C, Fetscher C, Schneider T, Krege S, Michel MC: Gender comparison of muscarinic receptor expression and function in rat and human urinary bladder: differential regulation of M2 and M3 receptors? Naunyn Schmiedebergs Arch Pharmacol. 2003 May;367(5):524-31. Epub 2003 Mar 28. [12669188 ]
  17. Morou E, Georgoussi Z: Expression of the third intracellular loop of the delta-opioid receptor inhibits signaling by opioid receptors and other G protein-coupled receptors. J Pharmacol Exp Ther. 2005 Dec;315(3):1368-79. Epub 2005 Sep 13. [16160084 ]

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Inhibitor of phospholipase A2, also possesses anti- coagulant properties. Also cleaves the cyclic bond of inositol 1,2-cyclic phosphate to form inositol 1-phosphate
Gene Name:
ANXA3
Uniprot ID:
P12429
Molecular weight:
36374.8
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Responsible for the provision of inositol required for synthesis of phosphatidylinositol and polyphosphoinositides and has been implicated as the pharmacological target for lithium action in brain. Can use myo-inositol monophosphates, myo-inositol 1,3-diphosphate, myo-inositol 1,4-diphosphate, scyllo-inositol-phosphate, glucose-1-phosphate, glucose-6-phosphate, fructose-1-phosphate, beta-glycerophosphate, and 2'-AMP as substrates.
Gene Name:
IMPA1
Uniprot ID:
P29218
Molecular weight:
36694.375
Reactions
Inositol phosphate + Water → Myoinositol + Phosphoric aciddetails
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Can use myo-inositol monophosphates, scylloinositol 1,4-diphosphate, glucose-1-phosphate, beta-glycerophosphate, and 2'-AMP as substrates. Has been implicated as the pharmacological target for lithium Li(+) action in brain.
Gene Name:
IMPA2
Uniprot ID:
O14732
Molecular weight:
31320.525
Reactions
Inositol phosphate + Water → Myoinositol + Phosphoric aciddetails
General function:
Involved in phosphatase activity
Specific function:
Lipid phosphatase which dephosphorylates phosphatidylinositol 3-monophosphate (PI3P) and phosphatidylinositol 3,5-bisphosphate (PI(3,5)P2). Has also been shown to dephosphorylate phosphotyrosine- and phosphoserine-containing peptides. Negatively regulates EGFR degradation through regulation of EGFR trafficking from the late endosome to the lysosome. Plays a role in vacuolar formation and morphology. Regulates desmin intermediate filament assembly and architecture. Plays a role in mitochondrial morphology and positioning. Required for skeletal muscle maintenance but not for myogenesis.
Gene Name:
MTM1
Uniprot ID:
Q13496
Molecular weight:
69931.09
Reactions
1D-Myo-inositol 1,3-bisphosphate + Water → Inositol phosphate + Phosphoric aciddetails
General function:
Involved in inositol-3-phosphate synthase activity
Specific function:
Key enzyme in myo-inositol biosynthesis pathway that catalyzes the conversion of glucose 6-phosphate to 1-myo-inositol 1-phosphate in a NAD-dependent manner. Rate-limiting enzyme in the synthesis of all inositol-containing compounds.
Gene Name:
ISYNA1
Uniprot ID:
Q9NPH2
Molecular weight:
55135.445
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
May play a role in the formation of skeletal elements derived through endochondral ossification, possibly by clearing adenosine 3',5'-bisphosphate produced by Golgi sulfotransferases during glycosaminoglycan sulfation (By similarity).
Gene Name:
IMPAD1
Uniprot ID:
Q9NX62
Molecular weight:
38681.15
Reactions
Inositol phosphate + Water → Myoinositol + Phosphoric aciddetails
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Has glycerophosphoinositol inositolphosphodiesterase activity and specifically hydrolyzes glycerophosphoinositol, with no activity for other substrates such as glycerophosphoinositol 4-phosphate, glycerophosphocholine, glycerophosphoethanolamine, and glycerophosphoserine. Accelerates the program of osteoblast differentiation and growth. May play a role in remodeling of the actin cytoskeleton (By similarity).
Gene Name:
GDPD2
Uniprot ID:
Q9HCC8
Molecular weight:
52185.905
Reactions
1-(sn-Glycero-3-phospho)-1D-myo-inositol + Water → Glycerol + Inositol phosphatedetails