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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:45:51 UTC
Update Date2023-02-21 17:27:59 UTC
HMDB IDHMDB0040227
Secondary Accession Numbers
  • HMDB40227
Metabolite Identification
Common NameIsopulegol acetate
DescriptionIsopulegol acetate 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. Based on a literature review a small amount of articles have been published on Isopulegol acetate.
Structure
Data?1677000479
Synonyms
ValueSource
Isopulegol acetic acidGenerator
1-Methyl-4-isopropenylcyclohexan-3-yl acetateHMDB
2-Isopropenyl-5-methylcyclohexyl acetateHMDB
5-Methyl-2-(1-methylethenyl)cyclohexanol acetateHMDB
Cyclohexanol, 5-methyl-2-(1-methylethenyl), acetateHMDB
FEMA 2965HMDB
Isopropenylcyclohexan-3-ol acetateHMDB
IsopulegolacetateHMDB
Isopulegyl acetateHMDB
P-Menth-8-en-3-yl acetateHMDB
(1R,2S,5R)-5-Methyl-2-(prop-1-en-2-yl)cyclohexyl acetic acidGenerator
(-)-Isopulegol acetic acidGenerator
Chemical FormulaC12H20O2
Average Molecular Weight196.286
Monoisotopic Molecular Weight196.146329884
IUPAC Name(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate
Traditional Name(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate
CAS Registry Number89-49-6
SMILES
C[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C
InChI Identifier
InChI=1S/C12H20O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3/t9-,11+,12-/m1/s1
InChI KeyHLHIVJRLODSUCI-ADEWGFFLSA-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
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point657.95 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.49 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.930 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.49ALOGPS
logP2.76ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.37 m³·mol⁻¹ChemAxon
Polarizability22.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.28531661259
DarkChem[M-H]-146.19631661259
DeepCCS[M+H]+150.27730932474
DeepCCS[M-H]-147.88130932474
DeepCCS[M-2H]-181.13930932474
DeepCCS[M+Na]+156.22430932474
AllCCS[M+H]+145.332859911
AllCCS[M+H-H2O]+141.332859911
AllCCS[M+NH4]+149.032859911
AllCCS[M+Na]+150.132859911
AllCCS[M-H]-149.132859911
AllCCS[M+Na-2H]-150.132859911
AllCCS[M+HCOO]-151.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isopulegol acetateC[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C1653.8Standard polar33892256
Isopulegol acetateC[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C1324.0Standard non polar33892256
Isopulegol acetateC[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C1298.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isopulegol acetate EI-B (Non-derivatized)splash10-0006-9300000000-cba940c1d1f1aaf19f8e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopulegol acetate EI-B (Non-derivatized)splash10-000f-9700000000-2ac8659513735c5f16082017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopulegol acetate EI-B (Non-derivatized)splash10-0006-9300000000-cba940c1d1f1aaf19f8e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isopulegol acetate EI-B (Non-derivatized)splash10-000f-9700000000-2ac8659513735c5f16082018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopulegol acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9400000000-782001fc756db8f2ed3e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopulegol acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 10V, Positive-QTOFsplash10-0002-0900000000-c310b45afbf8bebec1402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 20V, Positive-QTOFsplash10-0a4s-5900000000-74e3c99e5e97bce0a7aa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 40V, Positive-QTOFsplash10-0aor-9100000000-7b358df4198c2d161d6c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 10V, Negative-QTOFsplash10-0f6t-0900000000-a51ca72efa8995b84a7d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 20V, Negative-QTOFsplash10-0udj-2900000000-5a26b25a09d1449267f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 40V, Negative-QTOFsplash10-0m53-5900000000-6e0fbbcee54aa6be42542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 10V, Positive-QTOFsplash10-0002-9500000000-93096a7d46cef7b4b6122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 20V, Positive-QTOFsplash10-001m-9400000000-3834eca8ad8d46f748bc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 40V, Positive-QTOFsplash10-00kf-9000000000-16c4be2637c6fc12fd2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 10V, Negative-QTOFsplash10-0a4i-9500000000-01f5d7361d665b4a2f292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 20V, Negative-QTOFsplash10-0a4i-9200000000-c7e76a2ea7308d0c72da2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopulegol acetate 40V, Negative-QTOFsplash10-0a4l-9000000000-4be60751d3ccfe7fd79a2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019941
KNApSAcK IDNot Available
Chemspider ID85346
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound94579
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1427131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.