Showing Compound Card for Levoinositol (CDB000143)

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Record Information
Version1.0
Created at2020-03-18 23:26:23 UTC
Updated at2020-11-18 16:34:50 UTC
CannabisDB IDCDB000143
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLevoinositol
DescriptionLevoinositol (also known as 1L-chiro-Inositol or L-chiro-inositol, abbreviated LCI) 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, with 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. Levoinositol is found in dandelion and is widely distributed in higher plants predominantly as its monomethyl ether. Levoinositol is one of the sugar alcohols found in cannabis plant (PMID: 6991645 ). 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 chiro-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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-InositolChEBI
(1R,2R,3S,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexolChEBI
1,2,4/3,5,6-cyclohexanehexolChEBI
cis-1,2,4-trans-3,5,6-CyclohexanehexolChEBI
D-InositolChEBI
DCIChEBI
1,2,4/3,5,6-cyclohexane-1,2,3,4,5,6-hexolKegg
(+)-chiro-InositolHMDB
1D-chiro-inositolHMDB
D-(+)-chiro-InositolHMDB
D-chiro-InositolHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.16
Monoisotopic Molecular Weight180.0634
IUPAC Name(1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
Traditional NameD-chiro-inositol
CAS Registry Number643-12-9
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+/m0/s1
InChI KeyCDAISMWEOUEBRE-LKPKBOIGSA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Sugar alcohol
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Polyol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.6ALOGPS
logP-3.8ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.78 m³·mol⁻¹ChemAxon
Polarizability16.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLevoinositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dr-9700000000-6cc8567e1b238f96f926Spectrum
Predicted GC-MSLevoinositol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9001040000-00e67b437c4329aee95dSpectrum
Predicted GC-MSLevoinositol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5cb39f92646251665ebf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-2aeb7708f31c772e2d952016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8900000000-74f89711a1c6891808a42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8b68ff47f846a8ca1ddd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-03ef8572289795275d9c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0570-9300000000-950a37bd331028801e9f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-c98742ed2c27fed8805b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0570-9700000000-4e8df481dc1f1c1247432021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ea5996664694b27554a82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-a3b1806f4d2d4bc9e4702021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-9500000000-40e1f34ad1ad2b894cd92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-5d72027b1e4acffd4c292021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0240209
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001138
KNApSAcK IDC00053119
Chemspider ID10254647
KEGG Compound IDC19891
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27372
References
General References
  1. 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 ]
  2. 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 ]