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Record Information
Version4.0
Creation Date2006-08-13 21:42:07 UTC
Update Date2017-09-27 08:24:28 UTC
HMDB IDHMDB0004586
Secondary Accession Numbers
  • HMDB04586
  • HMDB06539
Metabolite Identification
Common NamePerillic acid
DescriptionPerillic acid is an intermediate in the Limonene and pinene degradation pathway. (KEGG). Its measurement in urine is used to monitor cancer patients receiving oral Limonene (a farnesyl transferase inhibitor that has shown antitumor properties)(PubMed ID 8723738 ).
Structure
Thumb
Synonyms
ValueSource
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidChEBI
4-Isopropenylcyclohex-1-enecarboxylic acidChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylateGenerator
PerillateGenerator
4-Isopropenylcyclohex-1-enecarboxylateGenerator
4-Isopropenylcyclohex-1-ene carboxylic acidMeSH
4-(2-Propenyl)-1-cyclohexane-1-carboxylic acidMeSH
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
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
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point60 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.428Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.63 g/LALOGPS
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
Bioavailability1ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected but not Quantified Adult (>18 years old)Both
    Schizophrenia
    details
    BloodDetected and Quantified6.02 (0.24-68.63) uMAdult (>18 years old)Female
    Breast cancer
    details
    Associated Disorders and Diseases
    Disease References
    Perillyl alcohol administration for cancer treatment
    1. Zhang Z, Chen H, Chan KK, Budd T, Ganapathi R: Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma. J Chromatogr B Biomed Sci Appl. 1999 May 14;728(1):85-95. [PubMed:10379660 ]
    Schizophrenia
    1. Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB 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)Download (PDF)
    General References
    1. Ripple GH, Gould MN, Arzoomanian RZ, Alberti D, Feierabend C, Simon K, Binger K, Tutsch KD, Pomplun M, Wahamaki A, Marnocha R, Wilding G, Bailey HH: Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day. Clin Cancer Res. 2000 Feb;6(2):390-6. [PubMed:10690515 ]
    2. Hudes GR, Szarka CE, Adams A, Ranganathan S, McCauley RA, Weiner LM, Langer CJ, Litwin S, Yeslow G, Halberr T, Qian M, Gallo JM: Phase I pharmacokinetic trial of perillyl alcohol (NSC 641066) in patients with refractory solid malignancies. Clin Cancer Res. 2000 Aug;6(8):3071-80. [PubMed:10955786 ]

    Enzymes

    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
    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
    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
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Not Available
    Gene Name:
    ALDH2
    Uniprot ID:
    P05091
    Molecular weight:
    56380.93
    Reactions
    Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails
    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
    Reactions
    Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails
    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
    Reactions
    Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails