| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:36:17 UTC |
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| Updated at | 2020-11-18 16:35:10 UTC |
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| CannabisDB ID | CDB000424 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Cannabielsoic acid B |
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| Description | Cannabielsoic acid B, also known as cannabielsoate B or CBEA-C5 B, is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabielsoic acid B is a dihydroxybenzoic acid derived from cannabidiolic acid. As such, 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, cannabielsoic acid B can be considered a polyketide, a monoterpenoid and a resorcinol derivative, due to the meta arrangement of its two hydroxil groups on the bencene ring. Cannabielsoic acid B, also belongs to the class of cannabis compounds known as Cannabielsoins. There are two types of cannabielsoic acids, cannabielsoic acid A (CBEA-C5 A) and cannabielsoic acid B (CBEA-C5 B). The inclusion of cannabielsoic acids as Cannabis natural products is somewhat controversial because they have been isolated and identified infrequently and also because they can be obtained by the photo-oxidation of CBD (cannabidiol). However, cannabielsoic acids have been repeatedly mentioned in the literature as natural cannabinoids and are considered as a part of the 120 cannabinoid compounds found in cannabis plants (PMID: 6991645 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| Cannabielsoate b | Generator |
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| Chemical Formula | C22H30O5 |
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| Average Molecular Weight | 374.48 |
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| Monoisotopic Molecular Weight | 374.2093 |
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| IUPAC Name | (1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-6-carboxylic acid |
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| Traditional Name | (1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-6-carboxylic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCCC1=CC2=C([C@@H]3[C@H](O2)[C@@](C)(O)CC[C@H]3C(C)=C)C(O)=C1C(O)=O |
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| InChI Identifier | InChI=1S/C22H30O5/c1-5-6-7-8-13-11-15-18(19(23)16(13)21(24)25)17-14(12(2)3)9-10-22(4,26)20(17)27-15/h11,14,17,20,23,26H,2,5-10H2,1,3-4H3,(H,24,25)/t14-,17+,20-,22-/m0/s1 |
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| InChI Key | OQCOBNKTUMOOHJ-RSGMMRJUSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Monoterpenoids |
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| Direct Parent | Aromatic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Aromatic monoterpenoid
- Hydroxybenzoic acid
- P-menthane monoterpenoid
- Coumaran
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Benzenoid
- Cyclic alcohol
- Tertiary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Ether
- Oxacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organooxygen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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|
Not Available | | Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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