Cannabis Compound Database: Showing Compound Card for Delta-9-tetrahydrocannabinolic acid B (CDB000017)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:35:37 UTC

Updated at

2020-11-18 16:35:09 UTC

CannabisDB ID

CDB000017

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Delta-9-tetrahydrocannabinolic acid B

Description

Delta-9-tetrahydrocannabinolic acid B or THC acid B, a delta 9-tetrahydrocannabinol, is one of the major non-psychoactive cannabinoid compounds that are found only in the cannabis plant. THC acid B, to a much lesser extent than THC acid A, is a biosynthetic precursor to delta-9-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. The difference between THC acid A and B is the position of the carboxyl functional group. In THC acid A it is on the C-2 whereas in THC acid B it is on the C-4 (PMID: 6991645 ). THC acid is produced via the following pathway: Geranyl pyrophosphate and olivetolic acid react, catalyzed by an enzyme Geranyl-pyrophosphate‚Äîolivetolic acid geranyltransferase to produce cannabigerolic acid which is then cyclized by the enzyme THC acid synthase to give THC acid. Over time, or when heated (via vaping or smoking), THC acid is decarboxylated, producing THC. While some studies showed that delta-9-THC acid binds cannabinoid type one (CB1) receptors with a Ki value of 23.5 nM (PMID: 25311884 ), others had found a negligible activity (PMID: 18303850 ). Decarboxylation of THC acid A to THC during storage or under certain experimental conditions may contribute to these contrasting results A recent study showed that freshly prepared and highly pure delta-9-THC acid (98%) has a low binding affinity for CB1 and CB2 receptors (PMID: 28861508 ). Thus, it seems that the biological activities of delta-9-THC acid are not mediated by interaction with these classical membrane receptors. Delta-9-THC acid exhibited anti-emetic and immune-modulatory activities through CB1-dependent and CB1-in- dependent mechanisms respectively (PMID: 16504929 ; PMID: 23889598 ). Delta-9-THC acid shows potent neuroprotective activity, that may aid in the treatment of Huntington's disease and possibly other neurodegenerative and neuroinflammatory diseases (PMID: 28853159 ).

Structure

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

Synonyms

Value	Source
(6AR,10as)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6ah,7H,8H,10ah-benzo[c]isochromene-4-carboxylate	Generator

Chemical Formula

C₂₂H₃₀O₄

Average Molecular Weight

358.48

Monoisotopic Molecular Weight

358.2144

IUPAC Name

(6aR,10aS)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-4-carboxylic acid

Traditional Name

(6aR,10aS)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCC1=C(C(O)=O)C2=C([C@H]3C=C(C)CC[C@H]3C(C)(C)O2)C(O)=C1

InChI Identifier

InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17(23)19-15-11-13(2)9-10-16(15)22(3,4)26-20(19)18(14)21(24)25/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16+/m0/s1

InChI Key

VITZNDKHSIWPSR-JKSUJKDBSA-N

Chemical Taxonomy

Classification

Not classified

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	5.11	ALOGPS
logP	5.6	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	103.99 m³·mol⁻¹	ChemAxon
Polarizability	41.13 Å³	ChemAxon
Number of Rings	3	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	Delta-9-tetrahydrocannabinolic acid B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delta-9-tetrahydrocannabinolic acid B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delta-9-tetrahydrocannabinolic acid B, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cannabinoid receptor 1	CNR1	6q14-q15	P21554	details
Cannabinoid receptor 2	CNR2	1p36.11	P34972	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

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 ]
Rosenthaler S, Pohn B, Kolmanz C, Huu CN, Krewenka C, Huber A, Kranner B, Rausch WD, Moldzio R: Differences in receptor binding affinity of several phytocannabinoids do not explain their effects on neural cell cultures. Neurotoxicol Teratol. 2014 Nov-Dec;46:49-56. doi: 10.1016/j.ntt.2014.09.003. Epub 2014 Oct 12. [PubMed:25311884 ]
Ahmed SA, Ross SA, Slade D, Radwan MM, Zulfiqar F, Matsumoto RR, Xu YT, Viard E, Speth RC, Karamyan VT, ElSohly MA: Cannabinoid ester constituents from high-potency Cannabis sativa. J Nat Prod. 2008 Apr;71(4):536-42. doi: 10.1021/np070454a. Epub 2008 Feb 28. [PubMed:18303850 ]
McPartland JM, MacDonald C, Young M, Grant PS, Furkert DP, Glass M: Affinity and Efficacy Studies of Tetrahydrocannabinolic Acid A at Cannabinoid Receptor Types One and Two. Cannabis Cannabinoid Res. 2017 May 1;2(1):87-95. doi: 10.1089/can.2016.0032. eCollection 2017. [PubMed:28861508 ]
Verhoeckx KC, Korthout HA, van Meeteren-Kreikamp AP, Ehlert KA, Wang M, van der Greef J, Rodenburg RJ, Witkamp RF: Unheated Cannabis sativa extracts and its major compound THC-acid have potential immuno-modulating properties not mediated by CB1 and CB2 receptor coupled pathways. Int Immunopharmacol. 2006 Apr;6(4):656-65. doi: 10.1016/j.intimp.2005.10.002. Epub 2005 Nov 7. [PubMed:16504929 ]
Rock EM, Kopstick RL, Limebeer CL, Parker LA: Tetrahydrocannabinolic acid reduces nausea-induced conditioned gaping in rats and vomiting in Suncus murinus. Br J Pharmacol. 2013 Oct;170(3):641-8. doi: 10.1111/bph.12316. [PubMed:23889598 ]
Nadal X, Del Rio C, Casano S, Palomares B, Ferreiro-Vera C, Navarrete C, Sanchez-Carnerero C, Cantarero I, Bellido ML, Meyer S, Morello G, Appendino G, Munoz E: Tetrahydrocannabinolic acid is a potent PPARgamma agonist with neuroprotective activity. Br J Pharmacol. 2017 Dec;174(23):4263-4276. doi: 10.1111/bph.14019. Epub 2017 Nov 2. [PubMed:28853159 ]

Showing Compound Card for Delta-9-tetrahydrocannabinolic acid B (CDB000017)

Structure for CDB000017 (Delta-9-tetrahydrocannabinolic acid B)