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Identification
YMDB IDYMDB00714
Name1D-myo-inositol 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionMyo-inositol 1-phosphate, also known as inositol 3-phosphoric acid, 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. Myo-inositol 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Myo-inositol 1-phosphate exists in all living species, ranging from bacteria to humans. myo-inositol 1-phosphate can be converted into myo-inositol through the action of the enzyme inositol monophosphatase 1. In yeast, myo-inositol 1-phosphate is involved in the metabolic pathway called the inositol phosphate metabolism pathway.
Structure
Thumb
Synonyms
  • 1D-myo-inositol 1-(dihydrogen phosphate)
  • 1d-myo-inositol 1-monophosphate
  • 1D-myo-Inositol 1-phosphate
  • 1l-myo-inositol 1-phosphate
  • d-myo-inositol 1-phosphate
  • D-Myo-Inositol-1-Phosphate
  • Inositol 1-monophosphate
  • inositol 1-phosphate
  • l-myo-inositol 1-phosphate
  • myo-inositol 1-phosphate
  • Myoinositol 1-phosphate
  • 1D-Myo-inositol 3-monophosphate
  • D-Myo-inositol 3-monophosphate
  • D-Myo-inositol 3-phosphate
  • Inositol 3-phosphate
  • Myoinositol 3-phosphate
  • Myo-inositol 3-phosphate
  • Myo-inositol 3-monophosphate
  • Inositol 3-monophosphate
  • 1D-Myo-inositol 3-monophosphoric acid
  • 1l-Myo-inositol 1-phosphoric acid
  • D-Myo-inositol 3-monophosphoric acid
  • D-Myo-inositol 3-phosphoric acid
  • Inositol 3-phosphoric acid
  • L-Myo-inositol 1-phosphoric acid
  • Myoinositol 3-phosphoric acid
  • Myo-inositol 3-phosphoric acid
  • Myo-inositol 3-monophosphoric acid
  • Inositol 3-monophosphoric acid
  • Myo-inositol 1-phosphoric acid
  • 1-(Dihydrogen phosphate) DL-myo-inositol
  • 1-(Dihydrogen phosphate) myo-inositol
  • DL-Myo-inositol 1-phosphate
  • Myo-inositol 1-monophosphate
  • Myo-inositol-1-phosphate
  • 1D-Myo-inositol 1-phosphoric acid
CAS number15421-51-9
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyINAPMGSXUVUWAF-UOTPTPDRSA-N
InChIInChI=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
IUPAC Name{[(1R,2S,3R,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}phosphonic acid
Traditional IUPAC Namemyo-inositol 1-phosphate
Chemical FormulaC6H13O9P
SMILESO[C@H]1[C@H](O)[C@@H](O)[C@H](OP(O)(O)=O)[C@H](O)[C@@H]1O
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility39.5 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.65 m³·mol⁻¹ChemAxon
Polarizability20.63 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Golgi
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Inositol MetabolismPW002498 ThumbThumb?image type=greyscaleThumb?image type=simple
Inositol phosphate metabolismPW002495 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Inositol phosphate metabolismec00562 Map00562
SMPDB ReactionsNot Available
KEGG Reactions
mannosylinositol phosphorylceramide + 1D-myo-inositol 1-phosphateinositol phosphomannosylinositol phosphoceramide
1D-myo-inositol 1-phosphate + N-(24-hydroxytetracosanoyl)sphinganineinositol-P-ceramide C (C26)
1D-myo-inositol 1-phosphate + N-(26-hydroxyhexacosanoyl)sphinganineinositol-P-ceramide C (C26)
N-(24-Hydroxytetracosanoyl)phytosphingosine + 1D-myo-inositol 1-phosphateinositol-P-ceramide C (C26)
N-(26-Hydroxyhexacosanyl)phytosphingosine + 1D-myo-inositol 1-phosphateinositol-P-ceramide C (C26)
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Hirsch, J. P., Henry, S. A. (1986). "Expression of the Saccharomyces cerevisiae inositol-1-phosphate synthase (INO1) gene is regulated by factors that affect phospholipid synthesis." Mol Cell Biol 6:3320-3328.3025587
  • Carman, G. M., Zeimetz, G. M. (1996). "Regulation of phospholipid biosynthesis in the yeast Saccharomyces cerevisiae." J Biol Chem 271:13293-13296.8663192
Synthesis Reference:Pirrung, 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.
External Links:
ResourceLink
CHEBI ID18297
HMDB IDHMDB02985
Pubchem Compound ID107737
Kegg IDC01177
ChemSpider ID24808130
FOODB IDFDB021907
WikipediaInositol phosphate
BioCyc IDCPD-180

Enzymes

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 involved in the inositol cycle of calcium signaling
Gene Name:
INM2
Uniprot ID:
Q05533
Molecular weight:
32092.40039
Reactions
Myo-inositol phosphate + H(2)O → myo-inositol + phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphorylinositol group onto ceramide to form inositol phosphorylceramide, an essential step in sphingolipid biosynthesis
Gene Name:
AUR1
Uniprot ID:
P36107
Molecular weight:
45192.80078
Reactions
General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphorylinositol group onto mannosyl phosphorylinositol ceramide to form mannosyl diphosphorylinositol ceramide
Gene Name:
IPT1
Uniprot ID:
P38954
Molecular weight:
60872.69922
Reactions
General function:
Involved in inositol-3-phosphate synthase activity
Specific function:
D-glucose 6-phosphate = 1D-myo-inositol 3- phosphate
Gene Name:
INO1
Uniprot ID:
P11986
Molecular weight:
59641.60156
Reactions
D-glucose 6-phosphate → 1D-myo-inositol 3-phosphate.
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Responsible for the provision of inositol required for synthesis of phosphatidylinositol and polyphosphoinositides
Gene Name:
INM1
Uniprot ID:
P38710
Molecular weight:
32823.0
Reactions
Myo-inositol phosphate + H(2)O → myo-inositol + phosphate.