Cannabis Compound Database: Showing Compound Card for Myoinositol (CDB000144)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (7) Show 13 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:26:25 UTC

Updated at

2020-12-07 19:07:10 UTC

CannabisDB ID

CDB000144

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Myoinositol

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. Inositol is one of the sugar alcohols and cyclitols identified in Cannabis sativa plants (PMID: 6991645 ). 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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.16

Monoisotopic Molecular Weight

180.0634

IUPAC Name

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

Traditional Name

L-inositol

CAS Registry Number

87-89-8

SMILES

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

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

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 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Osmolyte

Molecular messenger:

Second messenger

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	225 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	143 mg/mL at 19 °C	Human Metabolome Project
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

EI-MS/GC-MS

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

Pathways

Name	SMPDB/Pathwhiz	KEGG
Inositol Metabolism
Galactose Metabolism
Phosphatidylinositol Phosphate Metabolism
Inositol Phosphate Metabolism
Joubert syndrome		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alpha-galactosidase A	GLA		P06280	details
CDP-diacylglycerol--inositol 3-phosphatidyltransferase	CDIPT	16p11.2	O14735	details
Inositol oxygenase	MIOX	22q13.3	Q9UGB7	details
Inositol monophosphatase 1	IMPA1	8q21.13-q21.3	P29218	details
Inositol monophosphatase 2	IMPA2	18p11.2	O14732	details
Glycerophosphodiester phosphodiesterase 1	GDE1	16p12-p11.2	Q9NZC3	details
Inositol monophosphatase 3	IMPAD1	8q12.1	Q9NX62	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Inositol oxygenase	MIOX	22q13.3	Q9UGB7	details
Inositol monophosphatase 1	IMPA1	8q21.13-q21.3	P29218	details
Inositol monophosphatase 2	IMPA2	18p11.2	O14732	details
Glycerophosphodiester phosphodiesterase 1	GDE1	16p12-p11.2	Q9NZC3	details
Inositol monophosphatase 3	IMPAD1	8q12.1	Q9NX62	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alpha-galactosidase A	GLA		P06280	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000211

DrugBank ID

DB13178

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17268

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Gateva A, Unfer V, Kamenov Z: The use of inositol(s) isomers in the management of polycystic ovary syndrome: a comprehensive review. Gynecol Endocrinol. 2018 Jul;34(7):545-550. doi: 10.1080/09513590.2017.1421632. Epub 2018 Jan 8. [PubMed:29309199 ]

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details

1. Alpha-galactosidase A

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: GLA
Uniprot ID:: P06280
Molecular weight:: Not Available

Enzyme Details

2. CDP-diacylglycerol--inositol 3-phosphatidyltransferase

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Catalyzes the biosynthesis of phosphatidylinositol (PtdIns) as well as PtdIns:inositol exchange reaction. May thus act to reduce an excessive cellular PtdIns content. The exchange activity is due to the reverse reaction of PtdIns synthase and is dependent on CMP, which is tightly bound to the enzyme.
Gene Name:: CDIPT
Uniprot ID:: O14735
Molecular weight:: 23538.47

Enzyme Details

3. Inositol oxygenase

General function:: Involved in iron ion binding
Specific function:: Not Available
Gene Name:: MIOX
Uniprot ID:: Q9UGB7
Molecular weight:: 33009.33

Enzyme Details

4. 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 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

Enzyme Details

5. Inositol monophosphatase 2

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

Enzyme Details

6. Glycerophosphodiester phosphodiesterase 1

General function:: Involved in glycerophosphodiester phosphodiesterase activity
Specific function:: Has glycerophosphoinositol phosphodiesterase activity. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:: GDE1
Uniprot ID:: Q9NZC3
Molecular weight:: 37718.04

Enzyme Details

7. Inositol monophosphatase 3

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

Only showing the first 10 proteins. There are 13 proteins in total.

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Showing Compound Card for Myoinositol (CDB000144)

Structure for CDB000144 (Myoinositol)

Enzymes