Showing Compound Card for Quebrachitol (CDB000368)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (5)transporters (5) Show 22 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:33:19 UTC
Updated at2020-12-07 19:07:23 UTC
CannabisDB IDCDB000368
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameQuebrachitol
DescriptionQuebrachitol or L-Quebrachitol or QCT, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Quebrachitol can also be classified as a cyclitol (a cyclic polyol). L-Quebrachitol is an optically active, hydrophilic, neutral molecule that is very water soluble. It exists as a white powder. It was first isolated in 1887 from the bark of Aspidosperma quebracho (a South American rubber tree species), from whence it received its name. Quebrachitol along with sucrose is one of the main sugars in the latex of rubber trees. Quebrachitol is a natural product that is found in a number of plants and plant foods, with the highest concentration being found in sea-buckthorn berries. L-Quebrachitol has also been detected, but not quantified in litchi, mugworts and in Cannabis sativa (PMID: 6991645 ). It shows a sweetening property half of that of sucrose but induces colic or diarrhea at concentration used to render the food palatable. Quebrachito has been shown to have gastroprotective effects against acute gastric lesions caused by NSAIDs (PMID: 28132388 ). It also acts as a platelet activating factor (PAF) inhibitor and binds to the platelet activating factor receptor (PAFR) at micromolar concentrations (PMID: 21060292 ). Quebrachito also appears to bind to a number of other proteins or protein targets including the IP3 receptor, β-glucosidase, PAFR, COX2, nitric oxide synthase, and K+ATP channels (PMID: 28132388 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC7H14O6
Average Molecular Weight194.18
Monoisotopic Molecular Weight194.079
IUPAC Name(1S,2R,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol
Traditional Name(1S,2R,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol
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-OUIVRQFQSA-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 DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point190 to 198 °CWikipedia
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
Polarizability18.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Nitric oxide synthase, endothelialNOS37q36P29474 details
Prostaglandin G/H synthase 2PTGS21q25.2-q25.3P35354 details
Cytosolic beta-glucosidaseGBA3Q9H227 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
ATP-sensitive inward rectifier potassium channel 1KCNJ111q24P48048 details
Inositol 1,4,5-trisphosphate receptor type 1ITPR13p26.1Q14643 details
Inositol 1,4,5-trisphosphate receptor type 2ITPR212p11Q14571 details
Inositol 1,4,5-trisphosphate receptor type 3ITPR36p21Q14573 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Nitric oxide synthase, endothelialNOS37q36P29474 details
Prostaglandin G/H synthase 2PTGS21q25.2-q25.3P35354 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Platelet-activating factor receptorPTAFR1p35-p34.3P25105 details
Inositol 1,4,5-trisphosphate receptor type 1ITPR13p26.1Q14643 details
Inositol 1,4,5-trisphosphate receptor type 2ITPR212p11Q14571 details
Inositol 1,4,5-trisphosphate receptor type 3ITPR36p21Q14573 details
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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. Wang D, Zhang S, Chang Z, Kong DX, Zuo Z: Quebrachitol: Global Status and Basic Research. Nat Prod Bioprospect. 2017 Feb;7(1):113-122. doi: 10.1007/s13659-017-0120-3. Epub 2017 Jan 28. [PubMed:28132388 ]
  3. Moharam BA, Jantan I, Jalil J, Shaari K: Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation. Molecules. 2010 Nov 3;15(11):7840-8. doi: 10.3390/molecules15117840. [PubMed:21060292 ]

Only showing the first 10 proteins. There are 22 proteins in total.

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Enzymes

Enzyme Details
1. Nitric oxide synthase, inducible
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
Enzyme Details
2. Nitric oxide synthase, brain
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR.
Gene Name:
NOS1
Uniprot ID:
P29475
Molecular weight:
160969.095
Enzyme Details
3. Nitric oxide synthase, endothelial
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets. Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
Gene Name:
NOS3
Uniprot ID:
P29474
Molecular weight:
133273.59
Enzyme Details
4. Prostaglandin G/H synthase 2
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
Enzyme Details
5. Cytosolic beta-glucosidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available

Transporters

Enzyme Details
1. Nitric oxide synthase, inducible
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
Enzyme Details
2. ATP-sensitive inward rectifier potassium channel 1
General function:
Involved in inward rectifier potassium channel activity
Specific function:
In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Gene Name:
KCNJ1
Uniprot ID:
P48048
Molecular weight:
44794.6
Enzyme Details
3. Inositol 1,4,5-trisphosphate receptor type 1
General function:
Involved in calcium channel activity
Specific function:
Intracellular channel that mediates calcium release from the endoplasmic reticulum following stimulation by inositol 1,4,5- trisphosphate
Gene Name:
ITPR1
Uniprot ID:
Q14643
Molecular weight:
313942.4
Enzyme Details
4. Inositol 1,4,5-trisphosphate receptor type 2
General function:
Involved in calcium channel activity
Specific function:
Receptor for inositol 1,4,5-trisphosphate, a second messenger that mediates the release of intracellular calcium
Gene Name:
ITPR2
Uniprot ID:
Q14571
Molecular weight:
308061.1
Enzyme Details
5. Inositol 1,4,5-trisphosphate receptor type 3
General function:
Involved in calcium channel activity
Specific function:
Receptor for inositol 1,4,5-trisphosphate, a second messenger that mediates the release of intracellular calcium
Gene Name:
ITPR3
Uniprot ID:
Q14573
Molecular weight:
304104.0

Only showing the first 10 proteins. There are 22 proteins in total.

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