Cannabis Compound Database: Showing Compound Card for Cannabigerol (CDB000003)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (3) Show 8 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:34:44 UTC

Updated at

2020-11-18 16:35:09 UTC

CannabisDB ID

CDB000003

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Cannabigerol

Description

Cannabigerol 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
CBG	Kegg
(E)-2-(3,7-Dimethylocta-2,6-dien-1-yl)-5-pentylbenzene-1,3-diol	PhytoBank
2-((2E)-3,7-Dimethylocta-2,6-dienyl)-5-pentylbenzene-1,3-diol	PhytoBank
CBG-C5	PhytoBank

Chemical Formula

C₂₁H₃₂O₂

Average Molecular Weight

316.49

Monoisotopic Molecular Weight

316.2402

IUPAC Name

2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-pentylbenzene-1,3-diol

Traditional Name

cannabigerol

CAS Registry Number

25654-31-3

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 Key

QXACEHWTBCFNSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monoterpenoid (CHEBI:69477 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.99	ALOGPS
logP	7.05	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	101.51 m³·mol⁻¹	ChemAxon
Polarizability	39.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cannabigerol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabigerol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, negative	splash10-014i-0918000000-c6b99556311f76c2004a	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 21V, negative	splash10-000f-0911000000-4163fe92cd7a114411d7	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, negative	splash10-000l-0900000000-9723a7eca9a6bb6bc72e	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 29V, negative	splash10-000f-1910000000-adca5dfdec36460d75cb	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, negative	splash10-000f-1910000000-7e8c1798deed97196b13	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 37V, negative	splash10-052g-2900000000-13e18cc4a834a5f11a99	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 43V, negative	splash10-0a4m-4900000000-5d906cad104acb5d37cf	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 49V, negative	splash10-0aor-6900000000-cf245384105d79b5917f	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 55V, negative	splash10-066r-9700000000-025783411c001800a551	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 63V, negative	splash10-066r-9300000000-373c5193e617d057b2d6	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 22V, negative	splash10-014l-0925000000-fa5eb99a927a59daacda	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 22V, negative	splash10-0002-2900000000-0a06722690e2a5cd0623	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 22V, negative	splash10-000i-0900000000-d5d66ed2552db5b02bab	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 22V, negative	splash10-001i-9000000000-e077e2a9714ea2481c9d	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 22V, negative	splash10-0006-0900000000-e5293c9c02455b748371	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 22V, negative	splash10-0a4i-0900000000-029d5f5472a74407e059	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 22V, negative	splash10-0002-0900000000-abe58a408dc1bdc67ffd	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, negative	splash10-0006-0900000000-34a6f1305db516f13b04	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-0006-0900000000-eecbc5e1cd744a546843	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, negative	splash10-053u-0900000000-9117660c9963e1f74944	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, negative	splash10-0a59-0900000000-114ff2b54dee5408df54	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, negative	splash10-0a59-0900000000-560302a97a461c4dba52	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 26V, negative	splash10-0a4i-1900000000-9e266cbbbc524c6cad00	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 29V, negative	splash10-0a4i-2900000000-c2414f1be9b77a77adcd	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, negative	splash10-0a4i-5900000000-a0a0e679baa6267144e5	Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alpha-2A adrenergic receptor	ADRA2A	10q24-q26	P08913	details
Alpha-2B adrenergic receptor	ADRA2B	2p13-q13	P18089	details
5-hydroxytryptamine receptor 1A	HTR1A	5q11.2-q13	P08908	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alpha-2A adrenergic receptor	ADRA2A	10q24-q26	P08913	details
Alpha-2B adrenergic receptor	ADRA2B	2p13-q13	P18089	details
5-hydroxytryptamine receptor 1A	HTR1A	5q11.2-q13	P08908	details
Cannabinoid receptor 1	CNR1	6q14-q15	P21554	details
Cannabinoid receptor 2	CNR2	1p36.11	P34972	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
8-Ball Kush	Detected and Quantified	15.800 mg/g dry wt	PMID: 30036388	details
9 Lb Hammer	Detected and Quantified	1.930 mg/g dry wt	PMID: 30036388	details
97 Sage	Detected and Quantified	13.900 mg/g dry wt	PMID: 30036388	details
Adonis	Detected and Quantified	7.220 mg/g dry wt	PMID: 30036388	details
Alien Blues	Detected and Quantified	2.6 +/- 0.6 mg/g dry wt	PMID: 30036388	details
Alien Dawg	Detected and Quantified	0.257 mg/g dry wt	Jiamin Zheng, Yil...	details
Alien Sour Apple	Detected and Quantified	2.760 mg/g dry wt	PMID: 30036388	details
Black Boss	Detected and Quantified	3.970 mg/g dry wt	PMID: 30036388	details
Blue Cherry Pie	Detected and Quantified	0.9 +/- 0.2 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	1.610 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	16.000 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	18.800 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	1 +/- 0.2 mg/g dry wt	PMID: 30036388	details
Bob Marley	Detected and Quantified	10.200 mg/g dry wt	PMID: 30036388	details
Bohdi Tree	Detected and Quantified	0.8 +/- 0 mg/g dry wt	PMID: 30036388	details
Chemdawg	Detected and Quantified	3.360 mg/g dry wt	PMID: 30036388	details
Chemdawg #4	Detected and Quantified	3.260 mg/g dry wt	PMID: 30036388	details
Cold Creek Kush	Detected and Quantified	3.1 +/- 1 mg/g dry wt	PMID: 30036388	details
Cookies and Cream	Detected and Quantified	22.800 mg/g dry wt	PMID: 30036388	details
Cosmic Lotus	Detected and Quantified	1.990 mg/g dry wt	PMID: 30036388	details
Crystal Cookies	Detected and Quantified	7 +/- 0.8 mg/g dry wt	PMID: 30036388	details
Dairy Queen	Detected and Quantified	4.880 mg/g dry wt	PMID: 30036388	details
Double Royal Kush	Detected and Quantified	5.6 +/- 0.9 mg/g dry wt	PMID: 30036388	details
FLO	Detected and Quantified	4.270 mg/g dry wt	PMID: 30036388	details
FLO	Detected and Quantified	5.3 +/- 0.9 mg/g dry wt	PMID: 30036388	details
Gabriola	Detected and Quantified	0.315 mg/g dry wt	Jiamin Zheng, Yil...	details
Goji OG	Detected and Quantified	3.970 mg/g dry wt	PMID: 30036388	details
Golden Cobra	Detected and Quantified	2.420 mg/g dry wt	PMID: 30036388	details
Golden Sage	Detected and Quantified	7.260 mg/g dry wt	PMID: 30036388	details
Gorilla Glue	Detected and Quantified	3.940 mg/g dry wt	PMID: 30036388	details
Gorilla Glue #4	Detected and Quantified	2.430 mg/g dry wt	PMID: 30036388	details
Grandaddy Purple	Detected and Quantified	3.2 +/- 0 mg/g dry wt	PMID: 30036388	details
Grape Stomper	Detected and Quantified	3.880 mg/g dry wt	PMID: 30036388	details
Grape Stomper	Detected and Quantified	3.980 mg/g dry wt	PMID: 30036388	details
Green Crack	Detected and Quantified	11.9 +/- 1.4 mg/g dry wt	PMID: 30036388	details
Green Crack 2015	Detected and Quantified	15.1 +/- 1.7 mg/g dry wt	PMID: 30036388	details
Hash Plant	Detected and Quantified	0.148 mg/g dry wt	PMID: 30036388	details
Hash Plant	Detected and Quantified	5.950 mg/g dry wt	PMID: 30036388	details
Hemlock	Detected and Quantified	7.120 mg/g dry wt	PMID: 30036388	details
Holy Power	Detected and Quantified	6.2 +/- 0.6 mg/g dry wt	PMID: 30036388	details
Island Honey	Detected and Quantified	0.164 mg/g dry wt	Jiamin Zheng, Yil...	details
Jabberwocky	Detected and Quantified	5.710 mg/g dry wt	PMID: 30036388	details
Jabberwocky	Detected and Quantified	6.430 mg/g dry wt	PMID: 30036388	details
Juanita	Detected and Quantified	0.7 +/- 0 mg/g dry wt	PMID: 30036388	details
Kandy Kush	Detected and Quantified	0.210 mg/g dry wt	PMID: 30036388	details
Kush Puppy	Detected and Quantified	2.710 mg/g dry wt	PMID: 30036388	details
La Choco	Detected and Quantified	5.960 mg/g dry wt	PMID: 30036388	details
Lavendar	Detected and Quantified	2.1 +/- 0.4 mg/g dry wt	PMID: 30036388	details
Lavendar	Detected and Quantified	5.3 +/- 1.7 mg/g dry wt	PMID: 30036388	details
Lavendar Jones 2015	Detected and Quantified	2.9 +/- 0.4 mg/g dry wt	PMID: 30036388	details
Lemon Balm	Detected and Quantified	2.860 mg/g dry wt	PMID: 30036388	details
Lemon Goji	Detected and Quantified	3.970 mg/g dry wt	PMID: 30036388	details
Lemon OG	Detected and Quantified	10.400 mg/g dry wt	PMID: 30036388	details
Lemon Sherbet	Detected and Quantified	21.900 mg/g dry wt	PMID: 30036388	details
Lemon Skunk	Detected and Quantified	13.100 mg/g dry wt	PMID: 30036388	details
Lohan	Detected and Quantified	3.820 mg/g dry wt	PMID: 30036388	details
Love Lace	Detected and Quantified	2.4 +/- 0.1 mg/g dry wt	PMID: 30036388	details
Maui Haze	Detected and Quantified	4.760 mg/g dry wt	PMID: 30036388	details
Moby Dick	Detected and Quantified	9.810 mg/g dry wt	PMID: 30036388	details
Moonshine Ghost Trane Haze	Detected and Quantified	3.880 mg/g dry wt	PMID: 30036388	details
Oracle	Detected and Quantified	6.7 +/- 0.5 mg/g dry wt	PMID: 30036388	details
Orange Skunk	Detected and Quantified	9.530 mg/g dry wt	PMID: 30036388	details
Pineapple Skunk	Detected and Quantified	2.290 mg/g dry wt	PMID: 30036388	details
Pipe Dream	Detected and Quantified	4.030 mg/g dry wt	PMID: 30036388	details
Platinum Buffalo	Detected and Quantified	2.3 +/- 0.2 mg/g dry wt	PMID: 30036388	details
Platinum Gorilla	Detected and Quantified	2.8 +/- 0.6 mg/g dry wt	PMID: 30036388	details
Platinum Scout	Detected and Quantified	4 +/- 0.5 mg/g dry wt	PMID: 30036388	details
Purple Eclipse	Detected and Quantified	6.630 mg/g dry wt	PMID: 30036388	details
Purple Fat Pie	Detected and Quantified	3.3 +/- 0.3 mg/g dry wt	PMID: 30036388	details
Quadra	Detected and Quantified	0.251 mg/g dry wt	Jiamin Zheng, Yil...	details
Rocket Fuel	Detected and Quantified	5.750 mg/g dry wt	PMID: 30036388	details
Romulin	Detected and Quantified	4.3 +/- 0.2 mg/g dry wt	PMID: 30036388	details
Rosetta Stone	Detected and Quantified	7.950 mg/g dry wt	PMID: 30036388	details
RX	Detected and Quantified	9.6 +/- 0.3 mg/g dry wt	PMID: 30036388	details
Sensi Star	Detected and Quantified	0.521 mg/g dry wt	Jiamin Zheng, Yil...	details
Skunk Haze	Detected and Quantified	0.808 mg/g dry wt	PMID: 30036388	details
Skywalker	Detected and Quantified	8.8 +/- 0.9 mg/g dry wt	PMID: 30036388	details
Skywalker OG	Detected and Quantified	1.670 mg/g dry wt	PMID: 30036388	details
Sour Willie	Detected and Quantified	0.5 +/- 0 mg/g dry wt	PMID: 30036388	details
Spectrum	Detected and Quantified	0.879 mg/g dry wt	PMID: 30036388	details
Star Bud	Detected and Quantified	2.830 mg/g dry wt	PMID: 30036388	details
Strawberry Fields	Detected and Quantified	11.800 mg/g dry wt	PMID: 30036388	details
Strawberry Fields	Detected and Quantified	16.700 mg/g dry wt	PMID: 30036388	details
Sunset Sherbet	Detected and Quantified	4.770 mg/g dry wt	PMID: 30036388	details
Sunset Sherbet	Detected and Quantified	5.250 mg/g dry wt	PMID: 30036388	details
Tangerine Dream	Detected and Quantified	0.276 mg/g dry wt	Jiamin Zheng, Yil...	details
Tangerine Dream	Detected and Quantified	0.297 mg/g dry wt	Jiamin Zheng, Yil...	details
Tangerine Dream	Detected and Quantified	1.440 mg/g dry wt	PMID: 30036388	details
The Sauce	Detected and Quantified	3.050 mg/g dry wt	PMID: 30036388	details
Thunderstruck	Detected and Quantified	2 +/- 0.5 mg/g dry wt	PMID: 30036388	details
Twisted Velvet	Detected and Quantified	20.8 +/- 1.7 mg/g dry wt	PMID: 30036388	details
Venom OG	Detected and Quantified	1.870 mg/g dry wt	PMID: 30036388	details
Walker Kush	Detected and Quantified	5.5 +/- 0.6 mg/g dry wt	PMID: 30036388	details
White Widow	Detected and Quantified	1.9 +/- 0.3 mg/g dry wt	PMID: 30036388	details
Wonder Woman	Detected and Quantified	31.300 mg/g dry wt	PMID: 30036388	details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20219

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cannabigerol

METLIN ID

Not Available

PubChem Compound

5315659

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

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 ]
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 ]
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 ]
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

Showing Compound Card for Cannabigerol (CDB000003)

Structure for CDB000003 (Cannabigerol)

Enzymes