Cannabis Compound Database: Showing Compound Card for Perillic acid (CDB005269)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:26:16 UTC

Updated at

2020-12-07 19:11:52 UTC

CannabisDB ID

CDB005269

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Perillic acid

Description

Perillic acid, also known as perillate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Perillic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Perillic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acid	ChEBI
4-Isopropenylcyclohex-1-enecarboxylic acid	ChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylate	Generator
4-Isopropenylcyclohex-1-enecarboxylate	Generator
Perillate	Generator
4-(2-Propenyl)-1-cyclohexane-1-carboxylic acid	HMDB
4-Isopropenylcyclohex-1-ene carboxylic acid	HMDB

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.22

Monoisotopic Molecular Weight

166.0994

IUPAC Name

4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid

Traditional Name

perillic acid

CAS Registry Number

7694-45-3

SMILES

CC(=C)C1CCC(=CC1)C(O)=O

InChI Identifier

InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)

InChI Key

CDSMSBUVCWHORP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:36999 )
cyclohexenecarboxylic acid (CHEBI:36999 )
Menthane monoterpenoids (C11924 )
Cyclic monoterpenes (C11924 )
Menthane monoterpenoids (LMPR0102090041 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Organ and components:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	60 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	1.428	Not Available

Predicted Properties

Property	Value	Source
logP	2.47	ALOGPS
logP	2.41	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	48.2 m³·mol⁻¹	ChemAxon
Polarizability	18.13 Å³	ChemAxon
Number of Rings	1	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

Type	Description	Splash Key	View
GC-MS	Perillic acid, 1 TMS, GC-MS Spectrum	splash10-05di-5910000000-bd8e6a99a4d3b55c9c03	Spectrum
GC-MS	Perillic acid, non-derivatized, GC-MS Spectrum	splash10-05di-5910000000-bd8e6a99a4d3b55c9c03	Spectrum
Predicted GC-MS	Perillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01c3-9400000000-e30b212c252a489b1c8e	Spectrum
Predicted GC-MS	Perillic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9520000000-332aa96c8aa0d2aeaa6e	Spectrum
Predicted GC-MS	Perillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-024i-3900000000-16e917430a8c841892fe	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ou-9100000000-68409596298e7b6acef3	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-024i-3900000000-16e917430a8c841892fe	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-9300000000-d7b3cfdc7e8d493dd44c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-9400000000-9c643ffb36f6610feaf2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-9400000000-8ccd2f8c0492b0e9ee03	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-0ebacf3cff2e0c00ef11	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-3900000000-7e99a34da9f2f609046d	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9100000000-0d037a2e706cc01ac722	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-64c170dab26143a9232f	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-0900000000-e177ee19741567205f44	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4900000000-c2703d191f77cac3113c	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-4900000000-1573b97140969b3484d3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-9400000000-96087ab5a6507e90b024	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9100000000-f029f29fe7fce219e4ee	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-0900000000-0fa4b2ff935b571f25b9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05r3-9400000000-afb4a1702515ac477382	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
4-trimethylaminobutyraldehyde dehydrogenase	ALDH9A1	1q23.1	P49189	details
Alpha-aminoadipic semialdehyde dehydrogenase	ALDH7A1	5q31	P49419	details
Aldehyde dehydrogenase family 1 member A3	ALDH1A3	15q26.3	P47895	details
Aldehyde dehydrogenase, mitochondrial	ALDH2	12q24.2	P05091	details
Fatty aldehyde dehydrogenase	ALDH3A2	17p11.2	P51648	details
Aldehyde dehydrogenase X, mitochondrial	ALDH1B1	9p11.1	P30837	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0004586

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

2266070

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1256

PDB ID

Not Available

ChEBI ID

36999

References

General References

Not Available

Enzymes

Enzyme Details

1. 4-trimethylaminobutyraldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:: ALDH9A1
Uniprot ID:: P49189
Molecular weight:: 56291.485

Enzyme Details

2. Alpha-aminoadipic semialdehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:: ALDH7A1
Uniprot ID:: P49419
Molecular weight:: 58486.74

Enzyme Details

3. Aldehyde dehydrogenase family 1 member A3

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:: ALDH1A3
Uniprot ID:: P47895
Molecular weight:: 56107.995

Enzyme Details

4. Aldehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P05091
Molecular weight:: 56380.93

Enzyme Details

5. Fatty aldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:: ALDH3A2
Uniprot ID:: P51648
Molecular weight:: 54847.36

Enzyme Details

6. Aldehyde dehydrogenase X, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:: ALDH1B1
Uniprot ID:: P30837
Molecular weight:: 57248.96

Showing Compound Card for Perillic acid (CDB005269)

Structure for CDB005269 (Perillic acid)

Enzymes