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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:24 UTC
Update Date2021-09-16 15:27:24 UTC
HMDB IDHMDB0002985
Secondary Accession Numbers
  • HMDB02985
Metabolite Identification
Common Namemyo-Inositol 6-phosphate
Descriptionmyo-Inositol 6-phosphate, also known as I6P or Ins(6)P, 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. Inositol phosphate is an intermediate step in the metabolism of glucose-6-phosphate into myo-inositol. myo-Inositol is synthesized from glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerized by INYNA1 into myo-inositol 1-phosphate, which is then dephosphorylated by IMPA1 to give myo-inositol.
Structure
Data?1600225364
Synonyms
ValueSource
D-myo-Inositol (6)-monophosphateChEBI
D-myo-Inositol (6)-phosphateChEBI
I6PChEBI
Ins(6)PChEBI
Ins6PChEBI
D-myo-Inositol (6)-monophosphoric acidGenerator
Inositol phosphoric acidGenerator, HMDB
D-myo-Inositol (6)-phosphoric acidGenerator
1D-myo-Inositol 6-phosphoric acidGenerator, HMDB
D-myo-Inositol 6-phosphateHMDB
D-myo-Inositol-6-monophosphateHMDB
Inositol 1-phosphateHMDB
Inositol monophosphateHMDB
Inositol phosphateHMDB
Inositophosphoric acidHMDB
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 Number111901-84-9
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 KeyINAPMGSXUVUWAF-XCMZKKERSA-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
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Nucleus
Biospecimen Locations
  • Feces
  • Prostate Tissue
Tissue Locations
  • Bladder
  • Brain
  • Kidney
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023090
KNApSAcK IDNot Available
Chemspider ID10465039
KEGG Compound IDNot Available
BioCyc IDCPD-6702
BiGG ID1484840
Wikipedia LinkInositol phosphate
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID64838
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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

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
myo-Inositol 6-phosphate + Water → myo-Inositol + Phosphatedetails
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
myo-Inositol 6-phosphate + Water → myo-Inositol + Phosphatedetails
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
D-myo-Inositol 1,3-bisphosphate + Water → myo-Inositol 6-phosphate + Phosphatedetails
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
myo-Inositol 6-phosphate + Water → myo-Inositol + Phosphatedetails
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
Glycerophosphoinositol + Water → Glycerol + myo-Inositol 6-phosphatedetails