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From the plant

CBNRA(Z)-CBGA (cannabinerolic acid)

(Z) isomer of CBGA, isolated in 1995; a secondary substrate of hemp synthases, with no known pharmacology.

Unscheduled
Level of detail

C₂₂H₃₂O₄

CID 9998639

Family
PhytocannabinoidMinor
Origin
Origin not established
Molar mass
360.50 g/mol

Updated on

In plain terms

Cannabinerolic acid, or (Z)-CBGA, is the twin of cannabigerolic acid (CBGA): same formula, but a side chain with a different geometry. It was isolated from cannabis leaves in 1995. The plant's enzymes can use it, less well than CBGA, and its effects in the body have never been studied.

Receptors and activity

    Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

    Measured effects

    Not characterised. No placebo-controlled human trial has measured the effects of CBNRA, so no level is shown.

    Levels computed from placebo-controlled human trials: difference from placebo on 100, at the dose and route stated. Read the method

    Pharmacology

    (Z)-CBGA, or cannabinerolic acid (abbreviated « CBNRA » on this page), is the (2Z) geometric isomer of CBGA: its monoterpene chain is of the neryl rather than the geranyl type. Isolated in 1995 from the leaves of a Mexican strain of Cannabis sativa (Taura et al.), with a structure confirmed by synthesis, it has no established origin in the plant. Cannabis synthases accept it as a secondary substrate: CBDA synthase converts it to CBDA with a kcat of 0.03 s⁻¹, against 0.19 s⁻¹ for CBGA (Taura 1996), and CBCA synthase to CBCA with a comparable Km but a lower Vmax (Morimoto 1998); both teams conclude that CBDA and CBCA are formed mainly from CBGA. No CB1 or CB2 affinity and no pharmacokinetic, metabolism or toxicology data have been published. It must not be confused with CBNA (cannabinolic acid), a CBN-type molecule.

    Key sources.

    History

    Source
    Cannabis sativa L.: isolated from the leaves of a Mexican strain (Taura et al. 1995, per Radwan et al. 2021). Origin not established: no enzyme forming this (Z) isomer has been described in the sources consulted.

    Biosynthetic pathway

    Origin not established: no enzyme forming (Z)-CBGA has been described in the sources consulted. What is established concerns the next steps: cannabis synthases accept it as a secondary substrate. CBDA synthase converts it to CBDA with a kcat of 0.03 s⁻¹, against 0.19 s⁻¹ for CBGA (Taura et al. 1996), and CBCA synthase converts it to CBCA with a Km of the same order as for CBGA but a lower Vmax (Morimoto et al. 1998). Both teams conclude that CBDA and CBCA are formed mainly from CBGA.

    Classification

    Family, origin and source verification

    Family

    Phytocannabinoid › Minor

    Presence in the plant

    Present in the plant; origin not established

    Chemistry

    Type CBG · C5 side chain · acid form

    Verification

    Every fact on this entry was checked against its primary sources on 20 October 2026.

    Wikipedia (English)

    No dedicated article.

    References

    1. Taura F., Morimoto S., Shoyama Y. 1995, Phytochemistry 39:457-458: cannabinerolic acid, a cannabinoid from Cannabis sativa (new tab)DOI 10.1016/0031-9422(94)00887-Y
    2. Radwan M.M. et al. 2021, Molecules 26:2774: inventory of cannabinoids, CBG-type subclass (new tab)PMID 34066753
    3. Taura F. et al. 1996, J Biol Chem 271:17411-17416: purification of CBDA synthase; kcat 0.19 s⁻¹ (CBGA) and 0.03 s⁻¹ (cannabinerolic acid) (new tab)PMID 8663284
    4. Morimoto S. et al. 1998, Phytochemistry 49:1525-1529: purification of CBCA synthase; CBGA and cannabinerolic acid as substrates (new tab)PMID 9862135
    5. PubChem CID 9998639: cannabinerolic acid (identifiers) (new tab)
    6. ANSM, consolidated list of substances classified as narcotics, updated 26/06/2026 (new tab)

    Identifiers

    Names

    Common name
    (Z)-CBGA (cannabinerolic acid)
    IUPAC name
    3-[(2Z)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxy-6-pentylbenzoic acid
    Other names
    cannabinerolic acid · CBNRA · cis-CBGA · (Z)-CBGA

    Identifiers

    Formula
    C₂₂H₃₂O₄
    PubChem CID
    9998639(new tab)
    ChEBI
    CHEBI:67080(new tab)
    InChIKey
    SEEZIOZEUUMJME-VBKFSLOCSA-N
    SMILES
    CCCCCC1=CC(=C(C(=C1C(=O)O)O)C/C=C(/C)\CCC=C(C)C)O

    Machine-readable entry (JSON)

    LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.