AFCDB: Myo-Inositol (FDB010547)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:11 UTC

Update date

2020-09-17 15:30:59 UTC

Primary ID

FDB010547

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Myo-Inositol

Description

Myo-Inositol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. In humans, most inositol is synthesized in the kidneys, typically in amounts of a few grams per day. It is found in many foods, particularly in cereals with high bran content. It is an isomer of glucose that has traditionally been a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in humans. Inositol is a cyclic polyalcohol that plays an important role as a second messenger in a cell, in the form of inositol phosphates. Inositol phospholipids are important in signal transduction. A possible health effect of inositols, including myo-inositol, was recently reviewed. The review concluded that myo-inositol, together with chiro-inositol, at a 40:1 ratio, were an important therapeutic strategy for the improvement of metabolic, hormonal, and reproductive aspects of polycystic ovarian syndrome (PMID: 29309199).

CAS Number

87-89-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H12O6

IUPAC name

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

InChI Identifier

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

InChI Key

CDAISMWEOUEBRE-GPIVLXJGSA-N

Isomeric SMILES

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

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

Classification

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 )

Ontology

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Osmolyte

Molecular messenger:

Second messenger

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.00%; H 6.71%; O 53.28%	DFC
Melting Point	Mp 225°	DFC
Boiling Point	Not Available
Experimental Water Solubility	143 mg/mL at 19 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	0
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Myo-Inositol, 6 TMS, GC-MS Spectrum	splash10-014j-0953000000-1571a0577293e96091b1	Spectrum
GC-MS	Myo-Inositol, 6 TMS, GC-MS Spectrum	splash10-00kb-0932000000-96ddc21293431d746ad2	Spectrum
GC-MS	Myo-Inositol, non-derivatized, GC-MS Spectrum	splash10-00kb-0942000000-b78076224adf13bade25	Spectrum
GC-MS	Myo-Inositol, non-derivatized, GC-MS Spectrum	splash10-00kb-0942000000-42c4e40d04b4f306535d	Spectrum
GC-MS	Myo-Inositol, 6 TMS, GC-MS Spectrum	splash10-00di-8942000000-f5d7abd38d6ff547a0a9	Spectrum
GC-MS	Myo-Inositol, 6 TMS, GC-MS Spectrum	splash10-066r-0975000000-df7304c12b6c9bdb0f76	Spectrum
GC-MS	Myo-Inositol, non-derivatized, GC-MS Spectrum	splash10-014j-0953000000-1571a0577293e96091b1	Spectrum
GC-MS	Myo-Inositol, non-derivatized, GC-MS Spectrum	splash10-00kb-0932000000-96ddc21293431d746ad2	Spectrum
GC-MS	Myo-Inositol, non-derivatized, GC-MS Spectrum	splash10-00kb-0942000000-b78076224adf13bade25	Spectrum
GC-MS	Myo-Inositol, non-derivatized, GC-MS Spectrum	splash10-00di-8942000000-f5d7abd38d6ff547a0a9	Spectrum
GC-MS	Myo-Inositol, non-derivatized, GC-MS Spectrum	splash10-066r-0975000000-df7304c12b6c9bdb0f76	Spectrum
Predicted GC-MS	Myo-Inositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dr-9700000000-18a13ab4150e6ebb20cd	Spectrum
Predicted GC-MS	Myo-Inositol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-9001040000-00e67b437c4329aee95d	Spectrum
Predicted GC-MS	Myo-Inositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myo-Inositol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0a59-3900000000-96084971c3e13a1e7451	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-001i-9000000000-1de17d7f53ca727e6d72	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0zh9-9000000000-bef910214341056a78aa	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-0900000000-41a49af846b1636763b5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-0900000000-06f9ecfccf30d40ef204	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-004i-0900000000-bca88f6782a8ed386223	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-004i-1900000000-500ab195d69568b8678b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-01ti-5900000000-a1657b54c985e2be1d19	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-000i-9600000000-325cbb8dbfdeafb2b31f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-000i-9200000000-9145a4766351204e723a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-000i-9100000000-2bbbcfa4733b749ec768	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-000i-9000000000-de0ec8731a152b612bb9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, negative	splash10-0079-9000000000-41d049d1feef94e190d4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-059i-9000000000-796e728daf28d5122dee	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-059i-9000000000-8643e206319f3008a8d4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-0abi-9000000000-98e61f19bc2842f2e97b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, negative	splash10-0ab9-9000000000-29aa062fc4d5341167b6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-03di-1900000000-5a2897fd032a959918b3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-000i-9000000000-71c4786b7034d5a0a0a9	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-5cb39f92646251665ebf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-2aeb7708f31c772e2d95	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08gi-8900000000-74f89711a1c6891808a4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8b68ff47f846a8ca1ddd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1900000000-03ef8572289795275d9c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0570-9300000000-950a37bd331028801e9f	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

10239179

ChEMBL ID

CHEMBL1222251

KEGG Compound ID

C00137

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

17268

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00211

CRC / DFC (Dictionary of Food Compounds) ID

FCS22-I:FCS22-I

EAFUS ID

1795

Dr. Duke ID

MYO-INOSITOL|INOSITOL|MESO-INOSITOL

BIGG ID

33990

KNApSAcK ID

C00001164

HET ID

INS

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Inositol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti alopecic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cirrhotic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti neuropathic			DUKE
cholesterolytic			DUKE
lipotropic			DUKE
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE
ubiquiot			DUKE

Enzymes

Name	Gene Name	UniProt ID
Alpha-galactosidase A	GLA	P06280

Pathways

Name	SMPDB Link	KEGG Link
Galactose Metabolism	SMP00043	map00052
Inositol Metabolism	SMP00011	map00562
Inositol Phosphate Metabolism	SMP00462	map00562
Phosphatidylinositol Phosphate Metabolism	SMP00463	map00562

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Myo-Inositol (FDB010547)

Structure for FDB010547 (Myo-Inositol)