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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:12:27 UTC
Update Date2021-09-14 15:45:23 UTC
HMDB IDHMDB0036143
Secondary Accession Numbers
  • HMDB36143
Metabolite Identification
Common NameMonomenthyl succinate
DescriptionMonomenthyl succinate 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 Monomenthyl succinate.
Structure
Data?1563862827
Synonyms
ValueSource
Monomenthyl succinic acidGenerator
FEMA 3810HMDB
mono[5-Methyl-2-(1-methylethyl)cyclohexyl] butanedioate, 9ciHMDB
4-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-4-oxobutanoateGenerator
Monomenthyl succinateMeSH
Chemical FormulaC14H24O4
Average Molecular Weight256.338
Monoisotopic Molecular Weight256.167459256
IUPAC Name4-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-4-oxobutanoic acid
Traditional Name4-[(2-isopropyl-5-methylcyclohexyl)oxy]-4-oxobutanoic acid
CAS Registry Number188709-97-9
SMILES
CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O
InChI Identifier
InChI=1S/C14H24O4/c1-9(2)11-5-4-10(3)8-12(11)18-14(17)7-6-13(15)16/h9-12H,4-8H2,1-3H3,(H,15,16)
InChI KeyBLILOGGUTRWFNI-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
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point61.5 - 62.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.096 g/LALOGPS
logP10(2.97) g/LALOGPS
logP10(2.93) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Acidic)4.69ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity67.49 m³·mol⁻¹ChemAxon
Polarizability28.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.85631661259
DarkChem[M-H]-160.02331661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Monomenthyl succinate,1TMS,#1CC1CCC(C(C)C)C(OC(=O)CCC(=O)O[Si](C)(C)C)C11874.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Monomenthyl succinate,1TBDMS,#1CC1CCC(C(C)C)C(OC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)C12112.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Monomenthyl succinate GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9210000000-46c47fcb57e2288b029c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monomenthyl succinate GC-MS (1 TMS) - 70eV, Positivesplash10-059m-9611000000-763ecfaa8ee0bcaff0532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monomenthyl succinate 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 - Monomenthyl succinate 10V, Positive-QTOFsplash10-0a4r-1690000000-3e25d500426c245aea392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 20V, Positive-QTOFsplash10-0a4r-6920000000-6bc3f00bbdc53e5804402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 40V, Positive-QTOFsplash10-0aor-9300000000-871d873ec478d17a20ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 10V, Negative-QTOFsplash10-0a4i-1590000000-f2336c7fbb0bdbf910aa2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 20V, Negative-QTOFsplash10-0a4i-3940000000-c57bae8ce454542ea05e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 40V, Negative-QTOFsplash10-0a4r-5900000000-98ca44dfc90cb4c6e8052016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 10V, Negative-QTOFsplash10-0a4i-4790000000-1e9136d02f28ddf961232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 20V, Negative-QTOFsplash10-0a4i-7900000000-abe5adadd4b760b8192f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 40V, Negative-QTOFsplash10-0a4i-9100000000-49f13b699bcf37d022d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 10V, Positive-QTOFsplash10-000b-9800000000-d0704ed01116f704a1a22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 20V, Positive-QTOFsplash10-008j-9400000000-b53c886a6186338e10c42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monomenthyl succinate 40V, Positive-QTOFsplash10-0ac3-9000000000-3823b28c90e93e61a9842021-09-23Wishart 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 IDFDB014994
KNApSAcK IDC00057181
Chemspider ID8374504
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10199004
PDB IDNot Available
ChEBI ID169181
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.