Showing Compound Card for Perillaldehyde (CDB000659)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:49:29 UTC
Updated at2020-12-07 19:07:37 UTC
CannabisDB IDCDB000659
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePerillaldehyde
DescriptionPerillaldehyde or perillyl aldehyde 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. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. p-Menthane consists of a 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. Perillyl aldehyde is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Perillaldehyde is a cherry, and fatty tasting compound found in herbs and spices. It is a natural organic compound found most abundantly in the annual herb perilla, but also in a wide variety of other plants and essential oils. It has also been reported to be a volatile component of cannabis plants (PMID: 26657499 ). Perillaldehyde, or volatile oils from perilla that are rich in perillaldehyde, are used as food additives for flavoring and in perfumery to add spiciness. Perillaldehyde can be readily converted to perilla alcohol, which is also used in perfumery. It has a mint-like, cinnamon odor and is primarily responsible for the flavor of perilla.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-Perillyl aldehydeMetaCyc
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
IUPAC Name(4R)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
Traditional Name(4R)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
CAS Registry Number5503-12-8
SMILES
CC(=C)[C@@H]1CCC(C=O)=CC1
InChI Identifier
InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m0/s1
InChI KeyRUMOYJJNUMEFDD-JTQLQIEISA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane 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 FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point237 °C at 745 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.97ALOGPS
logP2.25ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.27 m³·mol⁻¹ChemAxon
Polarizability17.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-93f536e9e8fea0a3f4992016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-782526b3813e79dfb68f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9100000000-0dd1165ad555b037ef422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-200f98d44579ee015dd32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-bb22a8402cb0094ac0502016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-3900000000-fe4501ac4f2041d445922016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-4978542bd2d23c1a54162021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9300000000-572dd6848e3911f243382021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6x-9800000000-182dd4989879b63e19452021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-0c3589b0c235a44421282021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frf-9000000000-ccd21b69c5faee0cc41a2021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Platelet glycoprotein 4CD367q11.2P16671 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Free fatty acid receptor 1FFAR119q13.1O14842 details
Free fatty acid receptor 4FFAR410q23.33Q5NUL3 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0302492
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004784
KNApSAcK IDNot Available
Chemspider ID1265924
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1548901
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Transporters

Enzyme Details
1. Platelet glycoprotein 4
General function:
Not Available
Specific function:
Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:
CD36
Uniprot ID:
P16671
Molecular weight:
53054.0