Showing metabocard for Perillic acid (BMDB0004586)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:43 UTC
Update Date2020-05-11 20:23:51 UTC
BMDB IDBMDB0004586
Secondary Accession Numbers
  • BMDB04586
Metabolite Identification
Common NamePerillic acid
DescriptionPerillic 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidChEBI
4-Isopropenylcyclohex-1-enecarboxylic acidChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylateGenerator
4-Isopropenylcyclohex-1-enecarboxylateGenerator
PerillateGenerator
4-(2-Propenyl)-1-cyclohexane-1-carboxylic acidHMDB
4-Isopropenylcyclohex-1-ene carboxylic acidHMDB
Chemical FormulaC10H14O2
Average Molecular Weight166.22
Monoisotopic Molecular Weight166.099379691
IUPAC Name4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid
Traditional Nameperillic acid
CAS Registry Number7694-45-3
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 KeyCDSMSBUVCWHORP-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane 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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point60 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.428Not Available
Predicted Properties
PropertyValueSource
logP2.47ALOGPS
logP2.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.2 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-05di-5910000000-bd8e6a99a4d3b55c9c03View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-05di-5910000000-bd8e6a99a4d3b55c9c03View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01c3-9400000000-e30b212c252a489b1c8eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9520000000-332aa96c8aa0d2aeaa6eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-024i-3900000000-16e917430a8c841892feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ou-9100000000-68409596298e7b6acef3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-024i-3900000000-16e917430a8c841892feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9300000000-d7b3cfdc7e8d493dd44cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9400000000-9c643ffb36f6610feaf2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9400000000-8ccd2f8c0492b0e9ee03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-0ebacf3cff2e0c00ef11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-3900000000-7e99a34da9f2f609046dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-0d037a2e706cc01ac722View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-64c170dab26143a9232fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-0900000000-e177ee19741567205f44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-c2703d191f77cac3113cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-4900000000-1573b97140969b3484d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9400000000-96087ab5a6507e90b024View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9100000000-f029f29fe7fce219e4eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-349584a3f625d5b5807fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-0900000000-0fa4b2ff935b571f25b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05r3-9400000000-afb4a1702515ac477382View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004586
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013215
KNApSAcK IDC00010870
Chemspider ID1218
KEGG Compound IDC11924
BioCyc IDNot Available
BiGG ID2266070
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1256
PDB IDNot Available
ChEBI ID36999
References
Synthesis ReferenceSemmler, F. W.; Zaar, B. Constituents of Ethereal Oils. Constitution of Perillaldehyde, C10H14O. Berichte der Deutschen Chemischen Gesellschaft (1911), 44 52-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available