Showing Compound Card for Cannabigerol (CDB000003)

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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
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
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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20219
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCannabigerol
METLIN IDNot Available
PubChem Compound5315659
PDB IDNot Available
ChEBI IDNot Available
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