Myoinositol (YMDB00173)

Identification

YMDB ID

YMDB00173

Name

Myoinositol

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

myo-Inositol, also known as inosite or MI, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. myo-Inositol is an extremely weak basic (essentially neutral) compound (based on its pKa). myo-Inositol exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

cis-1,2,3,5-trans-4,6-Cyclohexanehexol
i-Inositol
iso-Inositol
Meat sugar
meso-Inositol
MI
Myo-Inositol
Myoinosite
Myoinositol
Phaseomannite
Rat antispectacled eye factor
(1R,2R,3S,4S,5R,6S)-Cyclohexane-1,2,3,4,5,6-hexol
1,2,3,4,5,6-HEXAHYDROXY-cyclohexane
1,2,3,5/4,6-cyclohexanehexol
1D-Myo-inositol
1l-Myo-inositol
Bios I
Cyclohexitol
D-Myo-inositol
Dambose
Inosite
Inositol
Ins
L-Myo-inositol
Inosital
Myo inositol
Vitamin b8

CAS number

87-89-8

Weight

Average: 180.1559
Monoisotopic: 180.063388116

InChI Key

CDAISMWEOUEBRE-GPIVLXJGSA-N

InChI

InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-

IUPAC Name

(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol

Traditional IUPAC Name

L-inositol

Chemical Formula

C₆H₁₂O₆

SMILES

[H]O[C@@]1([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]([H])(O[H])[C@]1([H])O[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

Alternative Parents

Substituents

Cyclohexanol
Sugar alcohol
Cyclitol or derivatives
Cyclic alcohol
Polyol
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

inositol (CHEBI:17268 )

Physical Properties

State

Solid

Charge

Melting point

225 °C

Experimental Properties

Property	Value	Reference
Water Solubility	143 mg/mL at 19 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	485 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.8	ChemAxon
logS	0.43	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.78 m³·mol⁻¹	ChemAxon
Polarizability	16.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
cell envelope
mitochondrion
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Inositol Metabolism	PW002498
Inositol phosphate metabolism	PW002495

KEGG Pathways

Galactose metabolism	ec00052
Inositol phosphate metabolism	ec00562

SMPDB Reactions

D-Myo-inositol 4-phosphate + water → Myoinositol + phosphate

1D-myo-inositol 3-phosphate + water → Myoinositol + phosphate

D-Myo-inositol 4-phosphate + water → Myoinositol + Phosphoric acid

Myoinositol + oxygen → D-Glucuronic acid + water

KEGG Reactions

1D-myo-inositol 1-phosphate + water → Myoinositol + phosphate

Myoinositol + CDP-diacylglycerol → Cytidine monophosphate + 1-Phosphatidyl-D-myo-inositol + hydron

Myoinositol + CDP-diacylglycerol ↔ Cytidine monophosphate + 1-Phosphatidyl-D-myo-inositol + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)	splash10-014j-0953000000-1571a0577293e96091b1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)	splash10-00kb-0932000000-96ddc21293431d746ad2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00kb-0942000000-b78076224adf13bade25	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00kb-0942000000-42c4e40d04b4f306535d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)	splash10-00di-8942000000-f5d7abd38d6ff547a0a9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-066r-0975000000-df7304c12b6c9bdb0f76	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014j-0953000000-1571a0577293e96091b1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0932000000-96ddc21293431d746ad2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0942000000-b78076224adf13bade25	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-8942000000-f5d7abd38d6ff547a0a9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-066r-0975000000-df7304c12b6c9bdb0f76	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dr-9700000000-18a13ab4150e6ebb20cd	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positive	splash10-00fr-9001040000-00e67b437c4329aee95d	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0a59-3900000000-96084971c3e13a1e7451	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-001i-9000000000-1de17d7f53ca727e6d72	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0zh9-9000000000-bef910214341056a78aa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-0900000000-41a49af846b1636763b5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-0900000000-06f9ecfccf30d40ef204	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-004i-0900000000-bca88f6782a8ed386223	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-004i-1900000000-500ab195d69568b8678b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-01ti-5900000000-a1657b54c985e2be1d19	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-000i-9600000000-325cbb8dbfdeafb2b31f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-000i-9200000000-9145a4766351204e723a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-000i-9100000000-2bbbcfa4733b749ec768	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-000i-9000000000-de0ec8731a152b612bb9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, negative	splash10-0079-9000000000-41d049d1feef94e190d4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-059i-9000000000-796e728daf28d5122dee	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-059i-9000000000-8643e206319f3008a8d4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-0abi-9000000000-98e61f19bc2842f2e97b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, negative	splash10-0ab9-9000000000-29aa062fc4d5341167b6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-03di-1900000000-5a2897fd032a959918b3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-000i-9000000000-71c4786b7034d5a0a0a9	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-5cb39f92646251665ebf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-2aeb7708f31c772e2d95	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08gi-8900000000-74f89711a1c6891808a4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8b68ff47f846a8ca1ddd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1900000000-03ef8572289795275d9c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0570-9300000000-950a37bd331028801e9f	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
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
Murray, M., Greenberg, M. L. (2000). "Expression of yeast INM1 encoding inositol monophosphatase is regulated by inositol, carbon source and growth stage and is decreased by lithium and valproate." Mol Microbiol 36:651-661.10844654
Nikawa, J., Yamashita, S. (1997). "Phosphatidylinositol synthase from yeast." Biochim Biophys Acta 1348:173-178.9370330
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Iselin, Beat M. Synthesis of inositol-5-monophosphoric acid and scyllitol monophosphoric acid. Journal of the American Chemical Society (1949), 71 3822-5.

External Links:

Resource	Link
CHEBI ID	17268
HMDB ID	HMDB00211
Pubchem Compound ID	892
Kegg ID	C00137
ChemSpider ID	23203338
FOODB ID	FDB010547
Wikipedia	Inositol
BioCyc ID	MYO-INOSITOL

Enzymes

Protein Details

1. CDP-diacylglycerol--inositol 3-phosphatidyltransferase

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: CDP-diacylglycerol + myo-inositol = CMP + phosphatidyl-1D-myo-inositol
Gene Name:: PIS1
Uniprot ID:: P06197
Molecular weight:: 24823.5

Reactions

CDP-diacylglycerol + myo-inositol → CMP + phosphatidyl-1D-myo-inositol.

Protein Details

2. Inositol monophosphatase 2

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.

Protein Details

3. Inositol monophosphatase 1

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.

Transporters

Protein Details

1. Myo-inositol transporter 1

General function:: Involved in transmembrane transporter activity
Specific function:: Major transporter for myo-inositol
Gene Name:: ITR1
Uniprot ID:: P30605
Molecular weight:: 63569.10156

Protein Details

2. Transposon Ty1-OL Gag-Pol polyprotein

General function:: Involved in DNA binding
Specific function:: Integrase (IN) targets the VLP to the nucleus, where a subparticle preintegration complex (PIC) containing at least integrase and the newly synthesized dsDNA copy of the retrotransposon must transit the nuclear membrane. Once in the nucleus, integrase performs the integration of the dsDNA into the host genome
Gene Name:: TY1B-OL
Uniprot ID:: Q12273
Molecular weight:: 198613.0

Reactions

Deoxynucleoside triphosphate + DNA(n) → diphosphate + DNA(n+1).

Structure for #<Compound:0xaef85058>

Enzymes

Reactions

Reactions

Reactions

Transporters

Reactions