Cannabis Compound Database: Showing Compound Card for Perillyl aldehyde (CDB005268)

Jump To Section:

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 19:26:10 UTC

Updated at

2020-12-07 19:11:51 UTC

CannabisDB ID

CDB005268

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Perillyl aldehyde

Description

Perillyl aldehyde, also known as fema no. 3557, 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. Thus, perillyl aldehyde is considered to be an isoprenoid lipid molecule. Perillyl aldehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Perillyl aldehyde 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-cyclohexene1-carboxyaldehyde	ChEBI
p-Mentha-1,8-dien-7-al	ChEBI
Perillal	ChEBI
Perillaldehyde	ChEBI
Perillic aldehyde	ChEBI
Perillylaldehyde	ChEBI
(-)-Perillaldehyde	HMDB
1,8-P-Menthadien-7-al	HMDB
1-Perillaldehyde	HMDB
4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde	HMDB
4-Isopropenylcyclohex-1-enecarbaldehyde	HMDB
Dihydrocuminyl aldehyde	HMDB
DL-Perillaldehyde(for perfumery)	HMDB
FEMA no. 3557	HMDB
L-Perillaldehyde	HMDB
P-Mentha-1,8-dien-7-al (natural)	HMDB
Para-mentha-1,8-dien-7-al	HMDB
Perilla aldehyde	HMDB, MeSH
4-Mentha-1,8-dien-7-al	MeSH, HMDB
Perillaldehyde, (+)-isomer	MeSH, HMDB

Chemical Formula

C₁₀H₁₄O

Average Molecular Weight

150.22

Monoisotopic Molecular Weight

150.1045

IUPAC Name

4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde

Traditional Name

(+)-perillaldehyde

CAS Registry Number

2111-75-3

SMILES

[H]C(=O)C1=CCC(CC1)C(C)=C

InChI Identifier

InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3

InChI Key

RUMOYJJNUMEFDD-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
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

aldehyde (CHEBI:15421 )
Menthane monoterpenoids (C02576 )
Cyclic monoterpenes (C02576 )
Menthane monoterpenoids (LMPR0102090010 )
a small molecule (CPD-1084 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	237 °C at 745 mmHg	Wikipedia
Water Solubility	Not Available	Not Available
logP	1.546	Not Available

Predicted Properties

Property	Value	Source
logP	2.97	ALOGPS
logP	2.25	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.27 m³·mol⁻¹	ChemAxon
Polarizability	17.3 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Perillyl aldehyde, non-derivatized, GC-MS Spectrum	splash10-005c-9700000000-a9b7244cc2e7179fa706	Spectrum
GC-MS	Perillyl aldehyde, non-derivatized, GC-MS Spectrum	splash10-014i-9400000000-a85682020d5afcb60c38	Spectrum
GC-MS	Perillyl aldehyde, non-derivatized, GC-MS Spectrum	splash10-016r-9200000000-489825eb61952c9dac22	Spectrum
GC-MS	Perillyl aldehyde, non-derivatized, GC-MS Spectrum	splash10-005c-9700000000-a9b7244cc2e7179fa706	Spectrum
Predicted GC-MS	Perillyl aldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-9400000000-34a520c15ee51fc09bad	Spectrum
Predicted GC-MS	Perillyl aldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0udi-0900000000-2d5f1aa73b10c86e86fd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0udi-0900000000-6a0c50ecfd39bc2355f1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0udi-1900000000-18ab37b64accb9eebc8a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0udi-1900000000-ff41ee428ac18fd92479	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0udi-2900000000-cc26f9d1f830b389dd6e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0udi-3900000000-b569eb4964b8859e157c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0ue9-3900000000-fc9bee20ab6457dc41d6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0zgl-6900000000-e4bd19c8534ad8a4170a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0kal-9800000000-7ae871e55ee7d93e3fd4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-0a5c-9500000000-20075ac27a31f7c011ff	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0kyl-9300000000-606866a64c1614c828b5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-00ou-9300000000-b59e349c4aa0f5f0f8b6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-00or-9200000000-20bc7958608312a537f3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-001i-2900000000-9efa35448eaa560e0b58	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-004i-9000000000-becd5fe890a229f54bb3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-001i-9000000000-faa2f39a1de11fcce372	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0a4i-4900000000-ff8554bb207ef1e44294	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-004i-9000000000-46d4cee1b5ac630ba9b8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-004i-9000000000-791c4364189bf936d4c3	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-93f536e9e8fea0a3f499	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-5900000000-782526b3813e79dfb68f	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxu-9100000000-0dd1165ad555b037ef42	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-200f98d44579ee015dd3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-bb22a8402cb0094ac050	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0159-3900000000-fe4501ac4f2041d44592	2016-08-03	View Spectrum

NMR

Not Available

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

HMDB0003647

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

Not Available

Wikipedia Link

Perillaldehyde

METLIN ID

Not Available

PubChem Compound

16441

PDB ID

Not Available

ChEBI ID

15421

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 Perillyl aldehyde (CDB005268)

Structure for CDB005268 (Perillyl aldehyde)

Enzymes