myo-inositol (CHEBI:17268)

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CHEBI:17268 - myo-inositol

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ChEBI Name	myo-inositol

ChEBI ID	CHEBI:17268

ChEBI ASCII Name	myo-inositol

Definition	An inositol having myo- configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43559, CHEBI:10601, CHEBI:12826, CHEBI:12831, CHEBI:25451

Supplier Information	ChemicalBook:CB8672575, eMolecules:530358

Download	Molfile XML SDF

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24 24 0 0 1 0 999 V2000

-0.6721 1.0998 0.4669 C 0 0 1 0 0 0 0 0 0 1 0 0

0.7245 1.2028 -0.2113 C 0 0 2 0 0 0 0 0 0 2 0 0

1.5243 -0.1304 -0.1883 C 0 0 2 0 0 0 0 0 0 3 0 0

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1.5139 2.2411 0.3694 O 0 0 0 0 0 0 0 0 0 0 0 0

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1.2525 -2.2530 -0.5814 H 0 0 0 0 0 0 0 0 0 0 0 0

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Wikipedia	License
In biochemistry, medicine, and related sciences, inositol generally refers to myo-inositol (formerly meso-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its formula is C6H12O6; the molecule has a ring of six carbon atoms, each with an hydrogen atom and a hydroxyl group (–OH). In myo-inositol, two of the hydroxyls, neither adjacent nor opposite, lie above the respective hydrogens relative to the mean plane of the ring. The compound is a carbohydrate, specifically a sugar alcohol (as distinct from aldoses like glucose) with half the sweetness of sucrose (table sugar). It is one of the most ancient components of living beings with multiple functions in eukaryotes, including structural lipids and secondary messengers. A human kidney makes about two grams per day from glucose, but other tissues synthesize it too. The highest concentration is in the brain, where it plays an important role in making other neurotransmitters and some steroid hormones bind to their receptors. In other tissues, it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation. In most mammalian cells the concentrations of myo-inositol are 5 to 500 times greater inside cells than outside them. A 2023 meta-analysis found that inositol is a safe and effective treatment in the management of polycystic ovary syndrome (PCOS). However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS. The other naturally occurring stereoisomers of cyclohexane-1,2,3,4,5,6-hexol are scyllo-, muco-, D-chiro-, L-chiro-, and neo-inositol, although they occur in minimal quantities compared to myo-inositol. The other possible isomers are allo-, epi-, and cis-inositol.
Read full article at Wikipedia

Formula

C6H12O6

Net Charge

Average Mass

180.15588

Monoisotopic Mass

180.06339

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-

InChIKey

CDAISMWEOUEBRE-GPIVLXJGSA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525)	See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). compatible osmolytes human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). nutrient A nutrient is a food component that an organism uses to survive and grow. EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor An EC 3.1.4.* (phosphoric diester hydrolase) inhibitor that interferes with the action of phosphatidylinositol-specific phospholipase C (EC 3.1.4.11). Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	myo-inositol (CHEBI:17268) has role Daphnia magna metabolite (CHEBI:83056) myo-inositol (CHEBI:17268) has role Escherichia coli metabolite (CHEBI:76971) myo-inositol (CHEBI:17268) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) myo-inositol (CHEBI:17268) has role compatible osmolytes (CHEBI:23366) myo-inositol (CHEBI:17268) has role EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor (CHEBI:64763) myo-inositol (CHEBI:17268) has role human metabolite (CHEBI:77746) myo-inositol (CHEBI:17268) has role mouse metabolite (CHEBI:75771) myo-inositol (CHEBI:17268) has role nutrient (CHEBI:33284) myo-inositol (CHEBI:17268) is a inositol (CHEBI:24848)

Incoming	α-D-Galp-(1→3)-β-D-Galf-(1→3)-α-D-Manp-(1→3)-α-D-Manp-(1→4)-α-D-GlcpN-(1→6)-1D-myo-inositol (CHEBI:61825) has functional parent myo-inositol (CHEBI:17268) α-D-Galp-(1→6)-α-D-Galp-(1→3)-β-D-Galf-(1→3)-α-D-Manp-(1→3)-α-D-Manp-(1→4)-α-D-GlcpN-(1→6)-myo-inositol (CHEBI:61830) has functional parent myo-inositol (CHEBI:17268) α-D-galactosyl-(1→3)-1D-myo-inositol (CHEBI:17505) has functional parent myo-inositol (CHEBI:17268) α-D-Manp-(1→2)-α-D-Manp-(1→2)-α-D-Manp-(1→6)-α-D-Manp-(1→6)-α-D-Manp-(1→6)-[α-D-Manp-(1→2)]-Ins (CHEBI:140998) has functional parent myo-inositol (CHEBI:17268) (α-D-Man)-(1→4)-(α-D-GlcN)-(1→6)-1-O-(6-thiohexylphosphono)-D-myo-inositol (CHEBI:61585) has functional parent myo-inositol (CHEBI:17268) (indol-3-ylacetyl)-myo-inositol 3-L-arabinoside (CHEBI:28071) has functional parent myo-inositol (CHEBI:17268) 1,3-bis(diphospho)-myo-inositol 2,4,5,6-tetrakisphosphate (CHEBI:62925) has functional parent myo-inositol (CHEBI:17268) 1,3-bis(diphospho)-myo-inositol 4,5,6-trisphosphate (CHEBI:62929) has functional parent myo-inositol (CHEBI:17268) 1,5-bis(diphospho)-1D-myo-inositol 2,3,4,6-tetrakisphosphate (CHEBI:62923) has functional parent myo-inositol (CHEBI:17268) 1,5-bis(diphospho)-1D-myo-inositol 3,4,6-trisphosphate (CHEBI:62931) has functional parent myo-inositol (CHEBI:17268) 1-acyl-sn-glycero-3-phospho-D-myo-inositol (CHEBI:28914) has functional parent myo-inositol (CHEBI:17268) 1-diphospho-1D-myo-inositol 2,3,4,5,6-pentakisphosphate (CHEBI:62919) has functional parent myo-inositol (CHEBI:17268) 1-diphospho-1D-myo-inositol 3,4,5,6-tetrakisphosphate (CHEBI:62926) has functional parent myo-inositol (CHEBI:17268) 1D-1-O-(indol-3-yl)acetyl-myo-inositol (CHEBI:15711) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,2,3,4,5-pentakisphosphate (CHEBI:18345) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,2,3,5,6-pentakisphosphate (CHEBI:48405) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,2,4,5,6-pentakisphosphate (CHEBI:16507) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,2,5,6-tetrakisphosphate (CHEBI:133328) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,2-cyclic phosphate (CHEBI:18426) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,3,4,5-tetrakisphosphate (CHEBI:16783) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,3,4-trisphosphate (CHEBI:18228) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,4,5,6-tetrakisphosphate (CHEBI:16067) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1,4-bisphosphate (CHEBI:17816) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 1-phosphate (CHEBI:18297) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 2,4-bisphosphate (CHEBI:133416) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 2-(L-cysteinylamino)-2-deoxy-α-D-glucopyranoside (CHEBI:52285) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 2-acetamido-2-deoxy-α-D-glucopyranoside (CHEBI:52442) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 2-acetamido-2-deoxy-α-D-glucopyranoside 3-phosphate (CHEBI:52443) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 2-amino-2-deoxy-α-D-glucopyranoside (CHEBI:52283) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 3,4,5,6-tetrakisphosphate (CHEBI:15844) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 3,4,6-trisphosphate (CHEBI:62918) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 3-phosphate (CHEBI:18169) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 4,5-bisphosphate (CHEBI:18156) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 4-phosphate (CHEBI:18384) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 5-phosphate (CHEBI:37493) has functional parent myo-inositol (CHEBI:17268) 1D-myo-inositol 6-phosphate (CHEBI:64838) has functional parent myo-inositol (CHEBI:17268) 1L-1-O-(indol-3-yl)acetyl-myo-inositol (CHEBI:52044) has functional parent myo-inositol (CHEBI:17268) 1L-myo-inositol 1,2,3,4,6-pentakisphosphate (CHEBI:11369) has functional parent myo-inositol (CHEBI:17268) 2-O-(indol-3-ylacetyl)-myo-inositol galactoside (CHEBI:19427) has functional parent myo-inositol (CHEBI:17268) 3,5-bis(diphospho)-1D-myo-inositol 1,2,4,6-tetrakisphosphate (CHEBI:62924) has functional parent myo-inositol (CHEBI:17268) 3,5-bis(diphospho)-1D-myo-inositol 1,4,6-trisphosphate (CHEBI:62930) has functional parent myo-inositol (CHEBI:17268) 3-(α-D-galactosyl)ononitol (CHEBI:133412) has functional parent myo-inositol (CHEBI:17268) 3-diphospho-1D-myo-inositol 1,2,4,5,6-pentakisphosphate (CHEBI:62922) has functional parent myo-inositol (CHEBI:17268) 3-diphospho-1D-myo-inositol 1,4,5,6-tetrakisphosphate (CHEBI:62927) has functional parent myo-inositol (CHEBI:17268) 4-diphospho-1D-myo-inositol pentakisphosphate (CHEBI:53064) has functional parent myo-inositol (CHEBI:17268) 5-diphospho-1D-myo-inositol pentakisphosphate (CHEBI:30164) has functional parent myo-inositol (CHEBI:17268) 5-diphospho-myo-inositol 1,3,4,6-tetrakisphosphate (CHEBI:62928) has functional parent myo-inositol (CHEBI:17268) 5-triphospho-1D-myo-inositol 1,2,3,4,6-pentakisphosphate (CHEBI:62985) has functional parent myo-inositol (CHEBI:17268) 6-(α-D-glucosaminyl)-1D-myo-inositol (CHEBI:44230) has functional parent myo-inositol (CHEBI:17268) 6-O-(2-amino-2-deoxy-α-D-glucosyl)-1D-myo-inositol 1-(6-mercaptohexyl)phosphate (CHEBI:61583) has functional parent myo-inositol (CHEBI:17268) 6-diphospho-1D-myo-inositol pentakisphosphate (CHEBI:53065) has functional parent myo-inositol (CHEBI:17268) myo-inositol 1,3,4,5,6-pentakisphosphate (CHEBI:16322) has functional parent myo-inositol (CHEBI:17268) myo-inositol 1,3,4,6-tetrakisphosphate (CHEBI:16155) has functional parent myo-inositol (CHEBI:17268) myo-inositol 1,3-bisphosphate (CHEBI:18225) has functional parent myo-inositol (CHEBI:17268) myo-inositol hexanicotinate (CHEBI:31699) has functional parent myo-inositol (CHEBI:17268) myo-inosose-5 (CHEBI:81197) has functional parent myo-inositol (CHEBI:17268) N-(2-hydroxyhexacosanoyl)phytosphingosine-1-phospho-(1D-myo-inositol) (CHEBI:139522) has functional parent myo-inositol (CHEBI:17268) [α-D-Man-(1→2)-α-D-Man-(1→2)-α-D-Man-(1→6)-α-D-Man-(1→4)-α-D-GlcN-(1→6)]-1-O-(6-thiohexylphosphono)-D-myo-inositol (CHEBI:61591) has functional parent myo-inositol (CHEBI:17268) [α-D-Man-(1→2)-α-D-Man-(1→6)-α-D-Man-(1→4)-α-D-GlcN-(1→6)]-1-O-(6-thiohexylphosphono)-D-myo-inositol (CHEBI:61588) has functional parent myo-inositol (CHEBI:17268) [α-D-Man-(1→2)-6-PEA-α-D-Man-(1→2)-α-D-Man-(1→6)-α-D-Man-(1→4)-α-D-GlcN-(1→6)]-1-O-(6-thiohexylphosphono)-D-myo-inositol (CHEBI:61592) has functional parent myo-inositol (CHEBI:17268) [α-D-Man-(1→2)-6-PEA-α-D-Man-(1→6)-α-D-Man-(1→4)-α-D-GlcN-(1→6)]-1-O-(6-thiohexylphosphono)-D-myo-inositol (CHEBI:146150) has functional parent myo-inositol (CHEBI:17268) [α-D-Man-(1→6)-α-D-Man-(1→4)-α-D-GlcN-(1→6)]-1-O-(6-thiohexylphosphono)-D-myo-inositol (CHEBI:61587) has functional parent myo-inositol (CHEBI:17268) [6-O-(2-aminoethylphosphono)-α-D-Man-(1→2)-α-D-Man-(1→6)-α-D-Man-(1→4)-α-D-GlcN-(1→6)]-1-O-(6-thiohexylphosphono)-D-myo-inositol (CHEBI:61590) has functional parent myo-inositol (CHEBI:17268) CDP-1L-myo-inositol (CHEBI:62566) has functional parent myo-inositol (CHEBI:17268) ethanolamine-P-6-α-Man-(1→2)-α-Man-(1→6)-[α-Gal-(1→2)-α-Gal-(1→6)-[α-Gal-(1→2)]-α-Gal-(1→3)]-α-Man-(1→4)-α-GlcN-(1→6)-inositol-1,2-cyclic phosphate (CHEBI:62865) has functional parent myo-inositol (CHEBI:17268) inositol C₂₀ phosphodihydroceramide(1−) (CHEBI:72460) has functional parent myo-inositol (CHEBI:17268) inositol phosphosphingolipid (CHEBI:53021) has functional parent myo-inositol (CHEBI:17268) Ins-1-P-6-Man-β1-3-Ins-1-P-Cer(t18:0/2-OH-26:0) (CHEBI:53005) has functional parent myo-inositol (CHEBI:17268) Ins-1-P-Cer(t18:0/2-OH-26:0) (CHEBI:53004) has functional parent myo-inositol (CHEBI:17268) Ins3P-(3P→5)-β-D-Araf-(1→2)-α-D-Araf-(1→5)-α-D-Araf-(1→5)-α-D-Araf (CHEBI:140781) has functional parent myo-inositol (CHEBI:17268) methyl myo-inositols (CHEBI:25270) has functional parent myo-inositol (CHEBI:17268) mycothiol (CHEBI:16768) has functional parent myo-inositol (CHEBI:17268) 6-O-(2-aminoethylphosphono)-α-D-Man-(1→2)-α-D-Man-(1→6)-α-D-Man-(1→4)-α-D-GlcN-(1→6)-D-myo-inositol (CHEBI:133453) is a myo-inositol (CHEBI:17268)

IUPAC Name

myo-inositol

Synonyms	Sources
(1r,2R,3S,4s,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol	IUPAC
1,2,3,4,5,6-HEXAHYDROXY-CYCLOHEXANE	PDBeChem
1,2,3,5/4,6-cyclohexanehexol	IUPAC
1D-myo-Inositol	KEGG COMPOUND
1L-myo-Inositol	KEGG COMPOUND
Bios I	KEGG COMPOUND
cis-1,2,3,5-trans-4,6-cyclohexanehexol	ChemIDplus
Cyclohexitol	KEGG COMPOUND
D-myo-Inositol	KEGG COMPOUND
Dambose	KEGG COMPOUND
i-inositol	ChEBI
inosite	ChEBI
Inositol	KEGG COMPOUND
Ins	ChEBI
L-myo-Inositol	KEGG COMPOUND
Meat sugar	KEGG COMPOUND
meso-Inositol	KEGG COMPOUND
myo-Inositol	KEGG COMPOUND
myo-inositol	UniProt
Myoinositol	HMDB

Manual Xrefs	Databases
1444	DrugCentral
C00001164	KNApSAcK
C00137	KEGG COMPOUND
D08079	KEGG DRUG
DB03106	DrugBank
HMDB0000211	HMDB
Inositol	Wikipedia
INS	PDBeChem
MYO-INOSITOL	MetaCyc
View more database links

Registry Numbers	Types	Sources
1907329	Reaxys Registry Number	Reaxys
82918	Gmelin Registry Number	Gmelin
87-89-8	CAS Registry Number	NIST Chemistry WebBook
87-89-8	CAS Registry Number	ChemIDplus

Citations	Types	Sources
11034685	PubMed citation	Europe PMC
11244303	PubMed citation	Europe PMC
11323092	PubMed citation	Europe PMC
11772411	PubMed citation	Europe PMC
12478879	PubMed citation	Europe PMC
12832083	PubMed citation	Europe PMC
14583919	PubMed citation	Europe PMC
14681857	PubMed citation	Europe PMC
15181167	PubMed citation	Europe PMC
15295080	PubMed citation	Europe PMC
15558078	PubMed citation	Europe PMC
16410747	PubMed citation	Europe PMC
1694860	PubMed citation	Europe PMC
17439666	PubMed citation	Europe PMC
17722064	PubMed citation	Europe PMC
18650262	PubMed citation	Europe PMC
18854045	PubMed citation	Europe PMC
19097871	PubMed citation	Europe PMC
19383710	PubMed citation	Europe PMC
22285975	PubMed citation	Europe PMC
22461977	PubMed citation	Europe PMC
22517104	PubMed citation	Europe PMC
838172	PubMed citation	Europe PMC

Last Modified

27 March 2024

CHEBI:17268 - myo-inositol

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