| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:35:05 UTC |
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| Updated at | 2020-11-18 16:35:09 UTC |
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| CannabisDB ID | CDB000008 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | Cannabichromevarinic acid |
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| Description | Cannabichromevarinic acid (CBCVA), a biosynthetic derivative of cannabigerovarinic acid (CBGVA), is a non-psychoactive component of cannabis. CBCVA is a C3 analogue of cannabichromenic acid. CBCVA is one of the more than 100 cannabinoids found in Cannabis sativa plants. As its precursor, cannabigerovarinic acid, CBCVA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabichromenic acid is characterized by the presence of a chromene (1-benzopyran) moiety in the center of the structure. This chromene arrangement results from the cyclization of the isoprenoid sidechain onto the hydroxyl group in position four of cannabigerovarinic acid, yielding a pyrane type ring. Cannabichromevarinic acid is a molecule of mixed biosynthetic oDOI: rigin, in which its aromatic moiety (derived from divarinic 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). As such, cannabichromevarinic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. CBCVA was one of four propyl cannabinoid acids isolated from Thai Cannabis, 'Meao Variant' in 1977 (DOI: 10.1248/cpb.25.2306). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2S)-5-Hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromene-6-carboxylate | Generator |
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| Chemical Formula | C20H26O4 |
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| Average Molecular Weight | 330.42 |
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| Monoisotopic Molecular Weight | 330.1831 |
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| IUPAC Name | (2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromene-6-carboxylic acid |
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| Traditional Name | (2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propylchromene-6-carboxylic acid |
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| CAS Registry Number | 64898-02-8 |
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| SMILES | CCCC1=CC2=C(C=C[C@](C)(CCC=C(C)C)O2)C(O)=C1C(O)=O |
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| InChI Identifier | InChI=1S/C20H26O4/c1-5-7-14-12-16-15(18(21)17(14)19(22)23)9-11-20(4,24-16)10-6-8-13(2)3/h8-9,11-12,21H,5-7,10H2,1-4H3,(H,22,23)/t20-/m0/s1 |
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| InChI Key | OIVPAQDCMDYIIL-FQEVSTJZSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Benzoic acids and derivatives |
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| Direct Parent | Salicylic acid and derivatives |
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| Alternative Parents | |
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| Substituents | - 1-benzopyran
- Salicylic acid or derivatives
- Benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- Vinylogous acid
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen 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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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Cannabichromevarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Cannabichromevarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Cannabichromevarinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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