Showing Compound Card for Cannabigerol (CDB000003)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 8 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:34:44 UTC
Updated at2022-12-13 20:57:25 UTC
CannabisDB IDCDB000003
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabigerol
DescriptionCannabigerol or CBG is the decarboxylated derivative of cannabigerolic acid, a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. CBG is a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. It is biosynthetically derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. It is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabigerol can be considered a polyketide, a monoterpenoid and a resorcinol. Cannabigerolic acid is a key biosynthetic precursor of Delta (9)-tetrahydrocannabinol, the main psychoactive component of Cannabis sativa. CBG is a minor constituent of cannabis (approximately 1% of dry weight). During growth, most of the CBG present in the plant‚Äôs tissues is converted into other cannabinoids, primarily tetrahydrocannabinol (THC) or cannabidiol (CBD) (PMID: 26836472 ). In contrast to THC (PMID 28120232 ), CBG antagonizes cannabinoid receptor type 1 (CB1) receptors and is both an alpha2-adrenoceptor agonist and moderate serotonin Type 1A (5HT1A) receptor antagonist (PMID: 20002104 ).  Cannabigerol has binding affinity for both CB1 and cannabinoid receptor type 2 (CB2). CBG is being investigated as a possible treatment for inflammatory diseases, such as colitis (PMID: 29562280 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-2-(3,7-Dimethyl-2,6-octadienyl)-5-pentyl-1,3-benzenediolChEBI
(e)-2-(3,7-Dimethyl-2,6-octadienyl)-5-pentyl-resorcinolChEBI
CBGKegg
(E)-2-(3,7-Dimethylocta-2,6-dien-1-yl)-5-pentylbenzene-1,3-diolPhytoBank
2-((2E)-3,7-Dimethylocta-2,6-dienyl)-5-pentylbenzene-1,3-diolPhytoBank
CBG-C5PhytoBank
Chemical FormulaC21H32O2
Average Molecular Weight316.49
Monoisotopic Molecular Weight316.2402
IUPAC Name2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-pentylbenzene-1,3-diol
Traditional Namecannabigerol
CAS Registry Number25654-31-3
SMILES
CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1
InChI Identifier
InChI=1S/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+
InChI KeyQXACEHWTBCFNSA-SFQUDFHCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic 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
logP6.99ALOGPS
logP7.05ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity101.51 m³·mol⁻¹ChemAxon
Polarizability39.04 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-MSCannabigerol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-014i-0918000000-c6b99556311f76c2004a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-000f-0911000000-4163fe92cd7a114411d72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-000l-0900000000-9723a7eca9a6bb6bc72e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-000f-1910000000-adca5dfdec36460d75cb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, negativesplash10-000f-1910000000-7e8c1798deed97196b132020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 37V, negativesplash10-052g-2900000000-13e18cc4a834a5f11a992020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 43V, negativesplash10-0a4m-4900000000-5d906cad104acb5d37cf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 49V, negativesplash10-0aor-6900000000-cf245384105d79b5917f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 55V, negativesplash10-066r-9700000000-025783411c001800a5512020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 63V, negativesplash10-066r-9300000000-373c5193e617d057b2d62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, negativesplash10-014l-0925000000-fa5eb99a927a59daacda2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, negativesplash10-0002-2900000000-0a06722690e2a5cd06232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, negativesplash10-000i-0900000000-d5d66ed2552db5b02bab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, negativesplash10-001i-9000000000-e077e2a9714ea2481c9d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, negativesplash10-0006-0900000000-e5293c9c02455b7483712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, negativesplash10-0a4i-0900000000-029d5f5472a74407e0592020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 22V, negativesplash10-0002-0900000000-abe58a408dc1bdc67ffd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-0006-0900000000-34a6f1305db516f13b042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-0006-0900000000-eecbc5e1cd744a5468432020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-053u-0900000000-9117660c9963e1f749442020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0a59-0900000000-114ff2b54dee5408df542020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0a59-0900000000-560302a97a461c4dba522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 26V, negativesplash10-0a4i-1900000000-9e266cbbbc524c6cad002020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-0a4i-2900000000-c2414f1be9b77a77adcd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, negativesplash10-0a4i-5900000000-a0a0e679baa6267144e52020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Alpha-2A adrenergic receptorADRA2A10q24-q26P08913 details
Alpha-2B adrenergic receptorADRA2B2p13-q13P18089 details
5-hydroxytryptamine receptor 1AHTR1A5q11.2-q13P08908 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Alpha-2A adrenergic receptorADRA2A10q24-q26P08913 details
Alpha-2B adrenergic receptorADRA2B2p13-q13P18089 details
5-hydroxytryptamine receptor 1AHTR1A5q11.2-q13P08908 details
Cannabinoid receptor 1CNR16q14-q15P21554 details
Cannabinoid receptor 2CNR21p36.11P34972 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified15.800 mg/g dry wt details
9 Lb HammerDetected and Quantified1.930 mg/g dry wt details
97 SageDetected and Quantified13.900 mg/g dry wt details
AdonisDetected and Quantified7.220 mg/g dry wt details
Alien BluesDetected and Quantified2.6 +/- 0.6 mg/g dry wt details
Alien DawgDetected and Quantified0.257 mg/g dry wt
    • David S. Wishart,...
 details
Alien Sour AppleDetected and Quantified2.760 mg/g dry wt details
Black BossDetected and Quantified3.970 mg/g dry wt details
Blue Cherry PieDetected and Quantified0.9 +/- 0.2 mg/g dry wt details
Blue DreamDetected and Quantified1.610 mg/g dry wt details
Blue DreamDetected and Quantified16.000 mg/g dry wt details
Blue DreamDetected and Quantified18.800 mg/g dry wt details
Blue DreamDetected and Quantified1 +/- 0.2 mg/g dry wt details
Bob MarleyDetected and Quantified10.200 mg/g dry wt details
Bohdi TreeDetected and Quantified0.8 +/- 0 mg/g dry wt details
ChemdawgDetected and Quantified3.360 mg/g dry wt details
Chemdawg #4Detected and Quantified3.260 mg/g dry wt details
Cold Creek KushDetected and Quantified3.1 +/- 1 mg/g dry wt details
Cookies and CreamDetected and Quantified22.800 mg/g dry wt details
Cosmic LotusDetected and Quantified1.990 mg/g dry wt details
Crystal CookiesDetected and Quantified7 +/- 0.8 mg/g dry wt details
Dairy QueenDetected and Quantified4.880 mg/g dry wt details
Double Royal KushDetected and Quantified5.6 +/- 0.9 mg/g dry wt details
FLODetected and Quantified4.270 mg/g dry wt details
FLODetected and Quantified5.3 +/- 0.9 mg/g dry wt details
GabriolaDetected and Quantified0.315 mg/g dry wt
    • David S. Wishart,...
 details
Goji OGDetected and Quantified3.970 mg/g dry wt details
Golden CobraDetected and Quantified2.420 mg/g dry wt details
Golden SageDetected and Quantified7.260 mg/g dry wt details
Gorilla GlueDetected and Quantified3.940 mg/g dry wt details
Gorilla Glue #4Detected and Quantified2.430 mg/g dry wt details
Grandaddy PurpleDetected and Quantified3.2 +/- 0 mg/g dry wt details
Grape StomperDetected and Quantified3.880 mg/g dry wt details
Grape StomperDetected and Quantified3.980 mg/g dry wt details
Green CrackDetected and Quantified11.9 +/- 1.4 mg/g dry wt details
Green Crack 2015Detected and Quantified15.1 +/- 1.7 mg/g dry wt details
Hash PlantDetected and Quantified0.148 mg/g dry wt details
Hash PlantDetected and Quantified5.950 mg/g dry wt details
HemlockDetected and Quantified7.120 mg/g dry wt details
Holy PowerDetected and Quantified6.2 +/- 0.6 mg/g dry wt details
Island HoneyDetected and Quantified0.164 mg/g dry wt
    • David S. Wishart,...
 details
JabberwockyDetected and Quantified5.710 mg/g dry wt details
JabberwockyDetected and Quantified6.430 mg/g dry wt details
JuanitaDetected and Quantified0.7 +/- 0 mg/g dry wt details
Kandy KushDetected and Quantified0.210 mg/g dry wt details
Kush PuppyDetected and Quantified2.710 mg/g dry wt details
La ChocoDetected and Quantified5.960 mg/g dry wt details
LavendarDetected and Quantified2.1 +/- 0.4 mg/g dry wt details
LavendarDetected and Quantified5.3 +/- 1.7 mg/g dry wt details
Lavendar Jones 2015Detected and Quantified2.9 +/- 0.4 mg/g dry wt details
Lemon BalmDetected and Quantified2.860 mg/g dry wt details
Lemon GojiDetected and Quantified3.970 mg/g dry wt details
Lemon OGDetected and Quantified10.400 mg/g dry wt details
Lemon SherbetDetected and Quantified21.900 mg/g dry wt details
Lemon SkunkDetected and Quantified13.100 mg/g dry wt details
LohanDetected and Quantified3.820 mg/g dry wt details
Love LaceDetected and Quantified2.4 +/- 0.1 mg/g dry wt details
Maui HazeDetected and Quantified4.760 mg/g dry wt details
Moby DickDetected and Quantified9.810 mg/g dry wt details
Moonshine Ghost Trane HazeDetected and Quantified3.880 mg/g dry wt details
OracleDetected and Quantified6.7 +/- 0.5 mg/g dry wt details
Orange SkunkDetected and Quantified9.530 mg/g dry wt details
Pineapple SkunkDetected and Quantified2.290 mg/g dry wt details
Pipe DreamDetected and Quantified4.030 mg/g dry wt details
Platinum BuffaloDetected and Quantified2.3 +/- 0.2 mg/g dry wt details
Platinum GorillaDetected and Quantified2.8 +/- 0.6 mg/g dry wt details
Platinum ScoutDetected and Quantified4 +/- 0.5 mg/g dry wt details
Purple EclipseDetected and Quantified6.630 mg/g dry wt details
Purple Fat PieDetected and Quantified3.3 +/- 0.3 mg/g dry wt details
QuadraDetected and Quantified0.251 mg/g dry wt
    • David S. Wishart,...
 details
Rocket FuelDetected and Quantified5.750 mg/g dry wt details
RomulinDetected and Quantified4.3 +/- 0.2 mg/g dry wt details
Rosetta StoneDetected and Quantified7.950 mg/g dry wt details
RXDetected and Quantified9.6 +/- 0.3 mg/g dry wt details
Sensi StarDetected and Quantified0.521 mg/g dry wt
    • David S. Wishart,...
 details
Skunk HazeDetected and Quantified0.808 mg/g dry wt details
SkywalkerDetected and Quantified8.8 +/- 0.9 mg/g dry wt details
Skywalker OGDetected and Quantified1.670 mg/g dry wt details
Sour WillieDetected and Quantified0.5 +/- 0 mg/g dry wt details
SpectrumDetected and Quantified0.879 mg/g dry wt details
Star BudDetected and Quantified2.830 mg/g dry wt details
Strawberry FieldsDetected and Quantified11.800 mg/g dry wt details
Strawberry FieldsDetected and Quantified16.700 mg/g dry wt details
Sunset SherbetDetected and Quantified4.770 mg/g dry wt details
Sunset SherbetDetected and Quantified5.250 mg/g dry wt details
Tangerine DreamDetected and Quantified0.276 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified1.440 mg/g dry wt details
The SauceDetected and Quantified3.050 mg/g dry wt details
ThunderstruckDetected and Quantified2 +/- 0.5 mg/g dry wt details
Twisted VelvetDetected and Quantified20.8 +/- 1.7 mg/g dry wt details
Venom OGDetected and Quantified1.870 mg/g dry wt details
Walker KushDetected and Quantified5.5 +/- 0.6 mg/g dry wt details
White WidowDetected and Quantified1.9 +/- 0.3 mg/g dry wt details
Wonder WomanDetected and Quantified31.300 mg/g dry wt details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4474921
KEGG Compound IDC20219
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCannabigerol
METLIN IDNot Available
PubChem Compound5315659
PDB IDNot Available
ChEBI ID69477
References
General References
  1. Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. [PubMed:26836472 ]
  2. Couch DG, Maudslay H, Doleman B, Lund JN, O'Sullivan SE: The Use of Cannabinoids in Colitis: A Systematic Review and Meta-Analysis. Inflamm Bowel Dis. 2018 Mar 19;24(4):680-697. doi: 10.1093/ibd/izy014. [PubMed:29562280 ]
  3. Morales P, Hurst DP, Reggio PH: Molecular Targets of the Phytocannabinoids: A Complex Picture. Prog Chem Org Nat Prod. 2017;103:103-131. doi: 10.1007/978-3-319-45541-9_4. [PubMed:28120232 ]
  4. Cascio MG, Gauson LA, Stevenson LA, Ross RA, Pertwee RG: Evidence that the plant cannabinoid cannabigerol is a highly potent alpha2-adrenoceptor agonist and moderately potent 5HT1A receptor antagonist. Br J Pharmacol. 2010 Jan;159(1):129-41. doi: 10.1111/j.1476-5381.2009.00515.x. Epub 2009 Dec 4. [PubMed:20002104 ]

Enzymes

Enzyme Details
1. Alpha-2A adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
Enzyme Details
2. Alpha-2B adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
Enzyme Details
3. 5-hydroxytryptamine receptor 1A
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3