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Record Information
Version3.6
Creation Date2006-08-13 21:42:07 UTC
Update Date2016-10-19 19:40:33 UTC
HMDB IDHMDB04586
Secondary Accession Numbers
  • 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
4-Prop-1-en-2-ylcyclohexene-1-carboxylateGenerator
4-Isopropenylcyclohex-1-enecarboxylateGenerator
PerillateHMDB
Chemical FormulaC10H14O2
Average Molecular Weight166.217
Monoisotopic Molecular Weight166.099379692
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 KeyInChIKey=CDSMSBUVCWHORP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • 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
Water Solubility1.63 mg/mLALOGPS
logP2.47ALOGPS
logP2.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.2 m3·mol-1ChemAxon
Polarizability18.13 Å3ChemAxon
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
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>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. [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. [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
NuGOwiki LinkHMDB04586
Metagene LinkHMDB04586
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. [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. [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