Showing Compound Card for alpha-Bisabolol (CDB000119)

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Record Information
Version1.0
Created at2020-03-18 23:25:29 UTC
Updated at2020-12-07 19:07:07 UTC
CannabisDB IDCDB000119
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Bisabolol
DescriptionAlpha-Bisabolol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ) Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Epi-Alpha-Bisabolol is an isomer of Bisabolol. Bisabolol or more formally α-(−)-bisabolol is a colorless viscous oil. Bisabolenes are present in the essential oils of German chamomile (PMID: 22096322 ), and of a wide variety of other plants including cubeb, lemon, oregano, and Cannabis sativa (PMID: 6991645 , 26657499 ). Various derivates of bisabolol also function as pheromones in different insects (PMID: 31659569 ). Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear (doi:10.3390/f11030290). Bisabolol has a weak sweet floral aroma and is used in various fragrances.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LevomenolKegg
(-)-a-BisabololGenerator
(-)-Α-bisabololGenerator
Bisabolol, (-)-isomerHMDB
BisabololHMDB
a-BisabololHMDB
Α-bisabololHMDB
(-)-(1's,2S)-alpha-BisabololHMDB
(-)-(1's,2S)-Α-bisabololHMDB
(-)-(1’S,2S)-α-bisabololHMDB
(-)-(4S,8S)-alpha-BisabololHMDB
(-)-(4S,8S)-Α-bisabololHMDB
(AlphaS,1S)-alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanolHMDB
(ΑS,1S)-α,4-dimethyl-α-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanolHMDB
alpha-(-)-BisabololHMDB
L-alpha-BisabololHMDB
L-Α-bisabololHMDB
Α-(-)-bisabololHMDB
(-)-alpha-BisabololHMDB
Chemical FormulaC15H26O
Average Molecular Weight222.37
Monoisotopic Molecular Weight222.1984
IUPAC Name(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
Traditional Namebisabolol
CAS Registry Number23089-26-1
SMILES
CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1
InChI Identifier
InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
InChI KeyRGZSQWQPBWRIAQ-CABCVRRESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.76ALOGPS
logP3.91ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-0.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.19 m³·mol⁻¹ChemAxon
Polarizability28.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSalpha-Bisabolol, non-derivatized, GC-MS Spectrumsplash10-066u-9500000000-198f9627399bbe1a8ae9Spectrum
Predicted GC-MSalpha-Bisabolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1290000000-205c7c190671df2e01412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05u2-9730000000-867964dcbacd7531be852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9400000000-531e5c4b5695ad0e8e092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-dc36029a7670fe05fa752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2190000000-aba6002bf895bc6a57622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9710000000-0aec4bfc3f14d590d3ba2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0290000000-4b15d43984c03b619c112021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kmi-1940000000-0ccfc6b1df77fb556c032021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059j-4920000000-a1ba351b509e5f240f4d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5j-7900000000-1f54ff8424c7d80eebe42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-4ce3d02192df7090cca82021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified0.374 mg/g dry wt details
97 SageDetected and Quantified0.336 mg/g dry wt details
AdonisDetected and Quantified0.834 mg/g dry wt details
Alien DawgDetected and Quantified0.26 mg/g dry wt
    • David S. Wishart,...
 details
Alien Sour AppleDetected and Quantified0.344 mg/g dry wt details
Animal CookiesDetected and Quantified0.4 +/- 0.3 mg/g dry wt details
Black BossDetected and Quantified0.595 mg/g dry wt details
Blue DreamDetected and Quantified0.059 mg/g dry wt details
Blue DreamDetected and Quantified2.148 mg/g dry wt details
Blue DreamDetected and Quantified2.221 mg/g dry wt details
Bubba KushDetected and Quantified0.9 +/- 0.5 mg/g dry wt details
Chemdawg #4Detected and Quantified0.824 mg/g dry wt details
Chemdawg #4Detected and Quantified1.376 mg/g dry wt details
ChemdogDetected and Quantified1 +/- 0.3 mg/g dry wt details
Cookies and CreamDetected and Quantified0.251 mg/g dry wt details
Cosmic LotusDetected and Quantified0.428 mg/g dry wt details
Dairy QueenDetected and Quantified0.423 mg/g dry wt details
Dark Shadow HazeDetected and Quantified0.438 mg/g dry wt details
Fortune CookiesDetected and Quantified0.6 +/- 0.2 mg/g dry wt details
GabriolaDetected and Quantified0.45 mg/g dry wt
    • David S. Wishart,...
 details
GasDetected and Quantified0.4 +/- 0.2 mg/g dry wt details
Goji OGDetected and Quantified0.469 mg/g dry wt details
Golden CobraDetected and Quantified0.360 mg/g dry wt details
Golden CobraDetected and Quantified0.36 mg/g dry wt details
Golden SageDetected and Quantified0.250 mg/g dry wt details
Golden SageDetected and Quantified0.25 mg/g dry wt details
Gorilla GlueDetected and Quantified1.234 mg/g dry wt details
Gorilla Glue #4Detected and Quantified1.168 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.9 +/- 0.2 mg/g dry wt details
Grizzly KushDetected and Quantified0.105 mg/g dry wt details
Hash PlantDetected and Quantified1.205 mg/g dry wt details
HemlockDetected and Quantified0.059 mg/g dry wt details
Island HoneyDetected and Quantified0.39 mg/g dry wt
    • David S. Wishart,...
 details
JabberwockyDetected and Quantified1.715 mg/g dry wt details
JabberwockyDetected and Quantified2.488 mg/g dry wt details
Jack HererDetected and Quantified0.463 mg/g dry wt details
Kush PuppyDetected and Quantified1.053 mg/g dry wt details
La ChocoDetected and Quantified1.566 mg/g dry wt details
Lemon BalmDetected and Quantified1.461 mg/g dry wt details
Lemon GojiDetected and Quantified0.312 mg/g dry wt details
Lemon SherbetDetected and Quantified0.267 mg/g dry wt details
Lemon SkunkDetected and Quantified0.274 mg/g dry wt details
Lemon SkunkDetected and Quantified0.378 mg/g dry wt details
Liberty HazeDetected and Quantified0.119 mg/g dry wt details
LohanDetected and Quantified0.284 mg/g dry wt details
Lucky CharmsDetected and Quantified0.628 mg/g dry wt details
Master KushDetected and Quantified1.1 +/- 0.2 mg/g dry wt details
Maui HazeDetected and Quantified1.187 mg/g dry wt details
Miami White KushDetected and Quantified0.7 +/- 0.2 mg/g dry wt details
Moby DickDetected and Quantified0.535 mg/g dry wt details
Moonshine Ghost Trane HazeDetected and Quantified0.554 mg/g dry wt details
Mr. NiceDetected and Quantified0.5 +/- 0.3 mg/g dry wt details
Nightmare CookieDetected and Quantified0.155 mg/g dry wt details
Og KushDetected and Quantified0.5 +/- 0.2 mg/g dry wt details
Orange SkunkDetected and Quantified0.265 mg/g dry wt details
Pineapple SkunkDetected and Quantified1.587 mg/g dry wt details
Platinum DelightDetected and Quantified0.337 mg/g dry wt details
Purple EclipseDetected and Quantified0.087 mg/g dry wt details
QuadraDetected and Quantified0.46 mg/g dry wt
    • David S. Wishart,...
 details
Rollex OGDetected and Quantified0.614 mg/g dry wt details
Rosetta StoneDetected and Quantified0.529 mg/g dry wt details
SatoriDetected and Quantified0.077 mg/g dry wt details
Sensi StarDetected and Quantified0.4 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.23 +/- 0.01 mg/g dry wt
    • David S. Wishart,...
 details
Skunk HazeDetected and Quantified0.398 mg/g dry wt details
Sour DieselDetected and Quantified0.9 +/- 0.3 mg/g dry wt details
SpectrumDetected and Quantified1.425 mg/g dry wt details
Star BudDetected and Quantified0.535 mg/g dry wt details
Star KillerDetected and Quantified0.791 mg/g dry wt details
Strawberry HazeDetected and Quantified0.6 +/- 0.1 mg/g dry wt details
Sunset SherbetDetected and Quantified0.469 mg/g dry wt details
Sunset SherbetDetected and Quantified0.519 mg/g dry wt details
Tahoe Og KushDetected and Quantified0.5 +/- 0.1 mg/g dry wt details
Tangerine DreamDetected and Quantified0.5 mg/g dry wt details
Tangerine Dream (Sativa dominant)Detected and Quantified0.34 +/- 0.02 mg/g dry wt
    • David S. Wishart,...
 details
The SauceDetected and Quantified0.18 mg/g dry wt details
The SauceDetected and Quantified0.180 mg/g dry wt details
Thin MintsDetected and Quantified0.4 +/- 0.2 mg/g dry wt details
Triple ODetected and Quantified0.4 +/- 0.3 mg/g dry wt details
Wonder WomanDetected and Quantified0.704 mg/g dry wt details
HMDB IDHMDB0036197
DrugBank IDDB13153
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003103 C00011607
Chemspider ID390796
KEGG Compound IDC09621
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442343
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. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  3. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
  4. Singh O, Khanam Z, Misra N, Srivastava MK: Chamomile (Matricaria chamomilla L.): An overview. Pharmacogn Rev. 2011 Jan;5(9):82-95. doi: 10.4103/0973-7847.79103. [PubMed:22096322 ]
  5. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  6. Yang CY, Seo MH, Lee SC: Male-Produced Aggregation Pheromone of the Sloe Bug, Dolycoris baccarum L. (Hemiptera: Heteroptera: Pentatomidae). J Chem Ecol. 2019 Oct;45(10):818-822. doi: 10.1007/s10886-019-01110-3. Epub 2019 Oct 28. [PubMed:31659569 ]
  7. Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
  8. Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. [PubMed:23746261 ]