Cannabis Compound Database: Showing Compound Card for Caryophyllene oxide (CDB000474)

Jump To Section:

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

Record Information

Version

1.0

Created at

2020-03-19 00:38:51 UTC

Updated at

2020-12-07 19:07:27 UTC

CannabisDB ID

CDB000474

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Caryophyllene oxide

Description

Caryophyllene oxide, an oxidation product of caryophyllene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679 ), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Caryophyllene oxide is neutral compound, a pale yellow white crystalline solid with a sweet, fresh, dry woody, spicy odor and an old wood, carrot, amber flavor ( Ref:DOI ). Caryophyllene oxide is one of the many sesquiterpenes found in cannabis plants and their essential oils. Caryophyllene oxide was isolated from cannabis plant ‚Äúdrug-type‚Äù with generally less caryophyllene oxide than ‚Äúfiber-type‚Äù (hemp) Cannabis (PMID: 6991645 ). Caryophyllene oxide is a volatile compound found in different species of citrus fruits ( Ref:DOI ). Almost 10% of caryophyllene oxide was detected in baccharis coridifolia oil from Argentina (9.80%) with 8.20%, found in guava leaf oil from Cuba, 5.10% in guava fruit oil from Reunion, 3.40% in curry wood leaf oil from Australia and 3.73% in lavender stem oil from Lithuania ( Ref:DOI ). By contrast, caryophyllene oxide is one of the major compounds found in the essential oil of Salvia spinosa (63.0%). Salvia spinosa essential oil has antimicrobial, cytotoxicity, antioxidant and enzyme inhibitory activities ( Ref:DOI ).

Structure

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

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.36

Monoisotopic Molecular Weight

220.1827

IUPAC Name

(1S,4R,6S,10R)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane

Traditional Name

(1S,4R,6S,10R)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane

CAS Registry Number

1139-30-6

SMILES

C[C@@]12CC[C@H]3[C@@H](CC3(C)C)C(=C)CC[C@@H]1O2

InChI Identifier

InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15+/m0/s1

InChI Key

NVEQFIOZRFFVFW-PWNZVWSESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Caryophyllane sesquiterpenoid
Sesquiterpenoid
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Role

Industrial application:

Household products:

Antimicrobial agent

Biological role:

Antioxidant

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	3.49	ALOGPS
logP	3.62	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.21 m³·mol⁻¹	ChemAxon
Polarizability	26.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Not Available

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	0.14 mg/g dry wt	David S. Wishart,...	details
Alien Dawg (Indica dominant)	Detected and Quantified	0.11 +/- 0.01 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.18 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.15 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.15 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.13 mg/g dry wt	David S. Wishart,...	details
Sensi Star (Pure Indica)	Detected and Quantified	0.09 +/- 0.00 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.15 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream (Sativa dominant)	Detected and Quantified	0.11 +/- 0.00 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

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

7067459

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 ]
Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. [PubMed:23746261 ]

Showing Compound Card for Caryophyllene oxide (CDB000474)

Structure for CDB000474 (Caryophyllene oxide)