Showing Compound Card for L-Quebrachitol (CDB000244)

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Record Information
Version1.0
Created at2020-03-19 00:26:36 UTC
Updated at2020-11-18 16:34:57 UTC
CannabisDB IDCDB000244
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Quebrachitol
DescriptionL-Quebrachitol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. L-Quebrachitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, L-Quebrachitol is found, on average, in the highest concentration within sea-buckthornberries. L-Quebrachitol has also been detected, but not quantified in, mugworts. This could make L-quebrachitol a potential biomarker for the consumption of these foods. It is also found in Cannabis sativa, in Paullinia pinnata and in seabuckthorn. For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made. It shows a sweetening property half of that of sucrose but induces colic or diarrhoea at concentration used to render the food palatable. Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials. It can be found in Allophylus edulis and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping. It was first isolated by Tanret in 1887 from the bark of Aspidosperma quebracho. The substance was tested as a sweetening agent for diabetics in 1933. Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-QuebrachitolHMDB
1l-2-O-Methyl-chiro-inositolHMDB
2-O-Methyl-L-chiro-inositolHMDB
QuebrachitolHMDB
Chemical FormulaC7H14O6
Average Molecular Weight194.18
Monoisotopic Molecular Weight194.079
IUPAC Name(1R,2S,3S,4S,5R,6R)-6-methoxycyclohexane-1,2,3,4,5-pentol
Traditional Name(-)-quebrachitol
CAS Registry Number642-38-6
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-/m0/s1
InChI KeyDSCFFEYYQKSRSV-FIZWYUIZSA-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:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point191 °CNot 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
Polarizability17.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Quebrachitol, non-derivatized, GC-MS Spectrumsplash10-066r-1793000000-bc79b0c3d616f4143f86Spectrum
GC-MSL-Quebrachitol, non-derivatized, GC-MS Spectrumsplash10-066r-1793000000-bc79b0c3d616f4143f86Spectrum
Predicted GC-MSL-Quebrachitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0h7i-4900000000-a49a1a34000c6d029ba2Spectrum
Predicted GC-MSL-Quebrachitol, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009m-7131590000-80d056ae2a5ea151f252Spectrum
Predicted GC-MSL-Quebrachitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Quebrachitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0006-0900000000-1ce4425a0b0cfc34ca392020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0006-0900000000-44fd82cd8dc60277e8fc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0006-1900000000-25d6598e8859b672af032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0006-2900000000-ca8f3b92cdb5acf778a22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0536-3900000000-108f6399b1e9a18df6e02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0536-5900000000-5e58d66f26e25cfb75ac2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-053u-7900000000-f0c18a8ff46d233e4d652020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-053r-9800000000-6fc4f22a443cc73e55912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-001i-9600000000-ec4617241721d864d2ff2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-001i-9300000000-ea89f1f1ee62b3e7b0bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-001i-9100000000-ff58f8d612bf11cc42822020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-0bu0-4900000000-4c9bd62fe8a94e82fbd62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-001i-9000000000-fc527ff9b17df8a45f5d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, positivesplash10-001i-9000000000-b6dea9b9985488301af82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-03di-0090000000-328674f186db37d3b0722020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-03di-0290000000-152601d8c3d3fb4a0f9b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-0690000000-f565a4869dd822c412712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0bt9-1950000000-99182114e2b761fbe8bb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0a59-7910000000-22057a91f9a822d9adb52020-07-22View Spectrum
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
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034221
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012526
KNApSAcK IDC00001169
Chemspider ID10254652
KEGG Compound IDC08257
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuebrachitol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID111
References
General ReferencesNot Available