Cannabis Compound Database: Showing Compound Card for Cannabidivarinic acid (CDB000014)

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Record Information

Version

1.0

Created at

2020-03-19 00:35:25 UTC

Updated at

2020-11-18 16:35:09 UTC

CannabisDB ID

CDB000014

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Cannabidivarinic acid

Description

Cannabidivarinic acid or CBDVA, belongs to the class of cannabis compounds known as cannabidiols. It is a non-psychoactive cannabinoid found in cannabis plants. CBDVA is the structural C4 analogue of cannabidiolic acid (CBDA), the natural precursor of cannabidiol (CBD). As such, CBDVA can also be considered a hydroxybenzoic acid derivative. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and, at least, one hydroxyl group. The biosynthesis of CBDVA occurs through the cyclization of the isoprenoid side chain of cannabigerovarinic acid (CBGVA) to yield a cyclohexene moiety, common to all cannabidiol-type cannabinoids ( Ref:DOI ). Unlike CBDA, research regarding the pharmacological properties of CBDVA is scarce.

Structure

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

Synonyms

Value	Source
Cannabidivarinate	Generator

Chemical Formula

C₂₀H₂₆O₄

Average Molecular Weight

330.42

Monoisotopic Molecular Weight

330.1831

IUPAC Name

2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-propylbenzoic acid

Traditional Name

2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-propylbenzoic acid

CAS Registry Number

Not Available

SMILES

CCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1C(O)=O

InChI Identifier

InChI=1S/C20H26O4/c1-5-6-13-10-16(21)18(19(22)17(13)20(23)24)15-9-12(4)7-8-14(15)11(2)3/h9-10,14-15,21-22H,2,5-8H2,1,3-4H3,(H,23,24)/t14-,15+/m0/s1

InChI Key

CZXWOKHVLNYAHI-LSDHHAIUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
Aromatic monoterpenoid
Hydroxybenzoic acid
Monocyclic monoterpenoid
P-menthane monoterpenoid
Salicylic acid
Salicylic acid or derivatives
Monoterpenoid
Benzoic acid
Phenylpropane
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	3.83	ALOGPS
logP	5.74	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.59 m³·mol⁻¹	ChemAxon
Polarizability	36.98 Å³	ChemAxon
Number of Rings	2	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	Cannabidivarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidivarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidivarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidivarinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidivarinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidivarinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cannabidivarinic acid, 3 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

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.00181 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.00189 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.000994 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.00173 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.00123 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.00261 mg/g dry wt	David S. Wishart,...	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

58828747

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

59444387

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Not Available

Showing Compound Card for Cannabidivarinic acid (CDB000014)

Structure for CDB000014 (Cannabidivarinic acid)