Showing Compound Card for d -bornesitol (CDB000243)

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Record Information
Version1.0
Created at2020-03-19 00:26:34 UTC
Updated at2020-11-18 16:34:57 UTC
CannabisDB IDCDB000243
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Named -bornesitol
DescriptionD-Bornesitol or bornesitol is the methyl ether dervative of myo-Inositol. Myo-Inositol is a cyclitol and an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It is also known as a sugar alcohol, having exactly 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. Inositol is a cyclic polyalcohol that plays an important role as a second messenger in the cells, in the form of inositol phosphates. It is found in many foods, particularly in cereals with high bran content. It is an isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in humans. Inositol phospholipids are important in signal transduction. Inositol is one of the sugar alcohols and cyclitols identified in Cannabis sativa plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1R,2R,3S,4S,5R,6S)-6-Methoxycyclohexane-1,2,3,4,5-pentolChEBI
1-O-Methyl-myo-inositolChEBI
BornesitolChEBI
D-(-)-BornesitolChEBI
1D-1-O-Methyl-myo-inositolKegg
(-)-BornesitolChEBI
D-1-O-Methyl-myo-inositolHMDB
D-BornesitolHMDB
Chemical FormulaC7H14O6
Average Molecular Weight194.18
Monoisotopic Molecular Weight194.079
IUPAC Name(1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol
Traditional Name(-)-bornesitol
CAS Registry Number484-71-9
SMILES
CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4+,5-,6-,7-/m1/s1
InChI KeyDSCFFEYYQKSRSV-AGZHHQKVSA-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
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Polyol
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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-2.7ALOGPS
logP-3.1ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.53 m³·mol⁻¹ChemAxon
Polarizability18.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSd -bornesitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0h7i-4900000000-a49a1a34000c6d029ba2Spectrum
Predicted GC-MSd -bornesitol, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009m-7131590000-80d056ae2a5ea151f252Spectrum
Predicted GC-MSd -bornesitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-bb4d2ecdce0dc04b10af2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-49945a3e6e17b3711a452016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05di-7900000000-0e8b87d7385a80fa9e172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-93626cc17042696dcb3d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1900000000-87660e9bdc50100350712016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05dr-9500000000-eaebcb725f72fdacd0302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-dfb1192d6d428bf6c9002021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9700000000-9adb95852c0c7a246d642021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-642c074f3107619845112021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-b2d0614c4acc67892c332021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-a87d8e09ecc6861cfb0c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-9000000000-9a20e62be6b376adb20f2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031437
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004281
KNApSAcK IDC00048928
Chemspider ID10254649
KEGG Compound IDC03659
BioCyc ID1-METHYL-MYO-INOSITOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18427
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 ]