Page last updated: 2024-12-11

cannabigerolic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

cannabigerolic acid: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cannabigerolic acid : A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
CannabisgenusThe plant genus in the Cannabaceae plant family, Urticales order, Hamamelidae subclass. The flowering tops are called many slang terms including pot, marijuana, hashish, bhang, and ganja. The stem is an important source of hemp fiber.[MeSH]CannabaceaeA plant family of the order Urticales, subclass Hamamelidae, class Magnoliopsida. It is most notable for the members, Cannabis and Hops.[MeSH]

Cross-References

ID SourceID
PubMed CID6449999
CHEMBL ID463843
CHEBI ID67081
SCHEMBL ID9909324
SCHEMBL ID16429144
MeSH IDM0264172

Synonyms (28)

Synonym
benzoic acid, 3-(3,7-dimethyl-2,6-octadienyl)-2,4-dihydroxy-6-pentyl-, (e)-
80i4zm847y ,
unii-80i4zm847y
25555-57-1
(e)-3-(3,7-dimethyl-2,6-octadienyl)-2,4-dihydroxy-6-pentylbenzoic acid
cannabigerolic acid
cbga
CHEMBL463843
chebi:67081 ,
AKOS005109070
3-[(2e)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxy-6-pentylbenzoic acid
C20406
3-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acid
.beta.-resorcylic acid, 3-(3,7-dimethyl-2,6-octadienyl)-6-pentyl-, (e)-
benzoic acid, 3-((2e)-3,7-dimethyl-2,6-octadien-1-yl)-2,4-dihydroxy-6-pentyl-
SCHEMBL9909324
SCHEMBL16429144
SEEZIOZEUUMJME-FOWTUZBSSA-N
Q27135612
cannabigerolic acid (cbga) 1000 microg/ml in acetonitrile
cannabigerolic acid (cbga) 100 microg/ml in acetonitrile
cannabigerolic acid (cbga) 250 microg/ml in acetonitrile
bdbm50532217
DTXSID401315426
cannabigerolic acid (cbga)
3-((2e)-3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid
beta-resorcylic acid, 3-(3,7-dimethyl-2,6-octadienyl)-6-pentyl-, (e)-
Z2587761296

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The aim of this study was to investigate similar dosing of CBG and CBGA from hemp plants that have been used for cannabidiol pharmacokinetic studies."( Single dose and chronic oral administration of cannabigerol and cannabigerolic acid-rich hemp extract in fed and fasted dogs: Physiological effect and pharmacokinetic evaluation.
Amstutz, K; Ellis, K; Gomez, B; Lyubimov, A; Schwark, WS; Venator, KP; Wakshlag, JJ; Zakharov, A, 2022
)
0.96

Bioavailability

ExcerptReferenceRelevance
" To this end, we have developed a stimulus-responsive, in situ-forming, nanoparticle-laden hydrogel for controlled release of poorly bioavailable drugs into the aqueous humor of the eye."( A stimulus-responsive, in situ-forming, nanoparticle-laden hydrogel for ocular drug delivery.
Derakhshandeh, M; Hatzikiriakos, SG; Hossain, S; Kabiri, M; Kamal, SH; Kumar, U; Pawar, SV; Roy, PR; Yadav, VG, 2018
)
0.48

Dosage Studied

ExcerptRelevanceReference
" The aim of this study was to investigate similar dosing of CBG and CBGA from hemp plants that have been used for cannabidiol pharmacokinetic studies."( Single dose and chronic oral administration of cannabigerol and cannabigerolic acid-rich hemp extract in fed and fasted dogs: Physiological effect and pharmacokinetic evaluation.
Amstutz, K; Ellis, K; Gomez, B; Lyubimov, A; Schwark, WS; Venator, KP; Wakshlag, JJ; Zakharov, A, 2022
)
0.96
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (5)

ClassDescription
dihydroxybenzoic acidAny member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.
diterpenoidAny terpenoid derived from a diterpene. The term includes compounds in which the C20 skeleton of the parent diterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
polyketideNatural and synthetic compounds containing alternating carbonyl and methylene groups ('beta-polyketones'), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations, etc. Considered by many to be synonymous with the less frequently used terms acetogenins and ketides.
resorcinolsAny benzenediol in which the two hydroxy groups are meta to one another.
phytocannabinoidA class of cannabinoid which are C21 terpenophenolic compounds isolated primarily from Cannabis sativa.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
N-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)IC50 (µMol)50.00000.70000.70000.7000AID1625159
Diacylglycerol lipase-alphaHomo sapiens (human)IC50 (µMol)30.50000.00101.05385.0119AID1625150
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
fatty acid metabolic processN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
sphingosine metabolic processN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
lipid catabolic processN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
N-acylethanolamine metabolic processN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
N-acylphosphatidylethanolamine metabolic processN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
monoacylglycerol biosynthetic processDiacylglycerol lipase-alphaHomo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayDiacylglycerol lipase-alphaHomo sapiens (human)
neuroblast proliferationDiacylglycerol lipase-alphaHomo sapiens (human)
arachidonic acid metabolic processDiacylglycerol lipase-alphaHomo sapiens (human)
diacylglycerol catabolic processDiacylglycerol lipase-alphaHomo sapiens (human)
retrograde trans-synaptic signaling by endocannabinoidDiacylglycerol lipase-alphaHomo sapiens (human)
regulation of neuroinflammatory responseDiacylglycerol lipase-alphaHomo sapiens (human)
cannabinoid biosynthetic processDiacylglycerol lipase-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
hydrolase activity, acting on carbon-nitrogen (but not peptide) bondsN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
N-acylsphingosine amidohydrolase activityN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
fatty acid amide hydrolase activityN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
N-(long-chain-acyl)ethanolamine deacylase activityN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
ceramidase activityN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
DNA-binding transcription factor bindingN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
protein bindingDiacylglycerol lipase-alphaHomo sapiens (human)
metal ion bindingDiacylglycerol lipase-alphaHomo sapiens (human)
acylglycerol lipase activityDiacylglycerol lipase-alphaHomo sapiens (human)
lipoprotein lipase activityDiacylglycerol lipase-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
cytoplasmN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
lysosomeN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
membraneN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
lysosomal lumenN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
extracellular exosomeN-acylethanolamine-hydrolyzing acid amidaseHomo sapiens (human)
plasma membraneDiacylglycerol lipase-alphaHomo sapiens (human)
early endosome membraneDiacylglycerol lipase-alphaHomo sapiens (human)
dendrite membraneDiacylglycerol lipase-alphaHomo sapiens (human)
dendritic spine membraneDiacylglycerol lipase-alphaHomo sapiens (human)
varicosityDiacylglycerol lipase-alphaHomo sapiens (human)
postsynaptic density membraneDiacylglycerol lipase-alphaHomo sapiens (human)
dendrite membraneDiacylglycerol lipase-alphaHomo sapiens (human)
cytoplasmDiacylglycerol lipase-alphaHomo sapiens (human)
postsynaptic membraneDiacylglycerol lipase-alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID362544Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 25923 after 18 hrs2008Journal of natural products, Aug, Volume: 71, Issue:8
Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.
AID1617278AUC in anesthetized C57BL/6J mouse brain at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1825218Antiviral activity against SARS-CoV-2 isolate USA-WA1/2020 strain infected in African green monkey Vero E6 cells assessed as inhibition of viral entry incubated for 1 hr prior to infection and measured after 48 hrs by Focus forming assay2022Journal of natural products, 01-28, Volume: 85, Issue:1
Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.
AID1625157Inhibition of FAAH in rat brain membranes at 50 uM using [14C]-AEA as substrate measured after 30 mins by scintillation counting method relative to control2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1617276Half life in anesthetized C57BL/6J mouse brain at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1625150Inhibition of recombinant human DAGLalpha expressed in COS7 cells using [14C]-oleoyl-2-arachidonoyl-glycerol as substrate measured after 20 mins by beta-counting method2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1617271Cmax in anesthetized C57BL/6J mouse plasma at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1625154Inhibition of MAGL in African green monkey COS cell homogenates at 100 uM using [3H]-arachidonoylglycerol as substrate measured after 20 mins by scintillation counting method relative to control2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1625162Inhibition of [14C]-AEA uptake in rat RBL2H3 cells by scintillation counting method2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID385376Binding affinity to CB1 receptor2008Journal of natural products, Apr, Volume: 71, Issue:4
Cannabinoid ester constituents from high-potency Cannabis sativa.
AID1617305Drug metabolism in plasma of anesthetized C57BL/6J mouse assessed as decrease in decarboxylation of parent compound at 10 mg/kg, ip by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1625159Inhibition of recombinant human NAAA expressed in HEK293 cells using [14C]-N-palmitoylethanolamine as substrate measured after 30 mins by beta-counting method2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1825217Antiviral activity against pseudovirus SARS-CoV-2 spike protein infected in HEK293T cells overexpressing ACE2 assessed as inhibition on pseudovirus infection incubated for 45 hrs by fluorescence microscopy2022Journal of natural products, 01-28, Volume: 85, Issue:1
Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.
AID1625163Inhibition of [14C]-AEA uptake in rat RBL2H3 cells at 25 uM by scintillation counting method relative to control2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1617273Tmax in anesthetized C57BL/6J mouse plasma at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID362546Antibacterial activity against epidemic methicillin-resistant Staphylococcus aureus 16 after 18 hrs2008Journal of natural products, Aug, Volume: 71, Issue:8
Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.
AID1825221Cytotoxicity against African green monkey Vero E6 cells by resazurin assay2022Journal of natural products, 01-28, Volume: 85, Issue:1
Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.
AID1625153Inhibition of MAGL in African green monkey COS cell homogenates using [3H]-arachidonoylglycerol as substrate measured after 20 mins by scintillation counting method2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1825216Antiviral activity against SARS-CoV-2 infected in African green monkey Vero E6 cells assessed as inhibition of viral entry at 25 ug/ml measured after 24 hrs post infection by fluorescence microscopy2022Journal of natural products, 01-28, Volume: 85, Issue:1
Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.
AID1625152Inhibition of recombinant human DAGLalpha expressed in COS7 cells at 100 uM using [14C]-oleoyl-2-arachidonoyl-glycerol as substrate measured after 20 mins by beta-counting method relative to control2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1825223Cytotoxicity against human HEK293T cells overexpressing ACE2 by resazurin assay2022Journal of natural products, 01-28, Volume: 85, Issue:1
Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.
AID362543Antibacterial activity against tetracycline-resistant Staphylococcus aureus XU212 after 18 hrs2008Journal of natural products, Aug, Volume: 71, Issue:8
Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.
AID1625160Inhibition of recombinant human NAAA expressed in HEK293 cells at 100 uM using [14C]-N-palmitoylethanolamine as substrate measured after 30 mins by beta-counting method relative to control2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1617272Cmax in anesthetized C57BL/6J mouse brain at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID362541Antibacterial activity against methicillin-resistant Staphylococcus aureus SA1199B after 18 hrs2008Journal of natural products, Aug, Volume: 71, Issue:8
Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.
AID1617277AUC in anesthetized C57BL/6J mouse plasma at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1617274Tmax in anesthetized C57BL/6J mouse brain at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1825220Antiviral activity against SARS-CoV-2 variant B.1.351 strain infected in African green monkey Vero E6 cells assessed as inhibition of viral entry incubated for 1 hr prior to infection and measured after 48 hrs by Focus forming assay2022Journal of natural products, 01-28, Volume: 85, Issue:1
Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.
AID1617270Ratio of drug level in anesthetized C57BL/6J mouse brain to plasma at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1617304Partition coefficient, log P of compound2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1782665Inhibition of human LDHB assessed as reduction in lactate production using pyruvate as substrate at 10 uM in presence of NADH by spectrophotometric analysis relative to control2021Journal of natural products, 05-28, Volume: 84, Issue:5
Cannabichromene and Δ
AID362542Antibacterial activity against macrolide-resistant Staphylococcus aureus RN4220 after 18 hrs2008Journal of natural products, Aug, Volume: 71, Issue:8
Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.
AID1825222Cytotoxicity against human Caco-2 cells by resazurin assay2022Journal of natural products, 01-28, Volume: 85, Issue:1
Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.
AID1625156Inhibition of FAAH in rat brain membranes using [14C]-AEA as substrate measured after 30 mins by scintillation counting method2019Journal of natural products, 03-22, Volume: 82, Issue:3
Plant-Based Modulators of Endocannabinoid Signaling.
AID1825219Antiviral activity against SARS-CoV-2 variant B.1.1.7 strain infected in African green monkey Vero E6 cells assessed as inhibition of viral entry incubated for 1 hr proir to infection and measured after 48 hrs by Focus forming assay2022Journal of natural products, 01-28, Volume: 85, Issue:1
Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants.
AID1617275Half life in anesthetized C57BL/6J mouse plasma at 10 mg/kg, ip administered as single dose measured upto 240 mins by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID1617303Dissociation constant, pKa of compound2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
AID362545Antibacterial activity against epidemic methicillin-resistant Staphylococcus aureus 15 after 18 hrs2008Journal of natural products, Aug, Volume: 71, Issue:8
Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.
AID1617306Drug metabolism in brain of anesthetized C57BL/6J mouse assessed as decrease in decarboxylation of parent compound at 10 mg/kg, ip by LC-MS/MS analysis2019Journal of natural products, 11-22, Volume: 82, Issue:11
Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (7.69)18.2507
2000's4 (15.38)29.6817
2010's9 (34.62)24.3611
2020's11 (42.31)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.24

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.24 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index5.14 (4.65)
Search Engine Demand Index44.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.85%)5.53%
Reviews2 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (88.46%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]