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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:19:19 UTC
Update Date2022-03-07 02:57:06 UTC
HMDB IDHMDB0041628
Secondary Accession Numbers
  • HMDB41628
Metabolite Identification
Common Name(+)-Neoisomenthol
Description(+)-Neoisomenthol, also known as iso-neomenthol, 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. Thus, (+)-neoisomenthol is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on (+)-Neoisomenthol.
Structure
Data?1563863684
Synonyms
ValueSource
(1alpha,2alpha,5alpha)-5-Methyl-2-(1-methylethyl)cyclohexanolChEBI
cis-1,3,cis-1,4-MentholChEBI
Iso-neomentholChEBI
(1a,2a,5a)-5-Methyl-2-(1-methylethyl)cyclohexanolGenerator
(1Α,2α,5α)-5-methyl-2-(1-methylethyl)cyclohexanolGenerator
(1R,3R,4R)-FormHMDB
P-Menthan-3-olHMDB
IsomentholMeSH
Chemical FormulaC10H20O
Average Molecular Weight156.2652
Monoisotopic Molecular Weight156.151415262
IUPAC Name(1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
Traditional Nameneoisomenthol
CAS Registry Number20752-34-5
SMILES
CC(C)[C@H]1CC[C@@H](C)C[C@H]1O
InChI Identifier
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9-,10-/m1/s1
InChI KeyNOOLISFMXDJSKH-OPRDCNLKSA-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
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-8 °CNot Available
Boiling Point215.38 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility434.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.216 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP2.68ALOGPS
logP2.66ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.45 m³·mol⁻¹ChemAxon
Polarizability19.45 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.98331661259
DarkChem[M-H]-136.8431661259
DeepCCS[M+H]+142.79830932474
DeepCCS[M-H]-140.43130932474
DeepCCS[M-2H]-174.92330932474
DeepCCS[M+Na]+149.72630932474
AllCCS[M+H]+135.832859911
AllCCS[M+H-H2O]+131.432859911
AllCCS[M+NH4]+139.832859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-141.332859911
AllCCS[M+Na-2H]-143.032859911
AllCCS[M+HCOO]-145.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-NeoisomentholCC(C)[C@H]1CC[C@@H](C)C[C@H]1O1626.6Standard polar33892256
(+)-NeoisomentholCC(C)[C@H]1CC[C@@H](C)C[C@H]1O1167.3Standard non polar33892256
(+)-NeoisomentholCC(C)[C@H]1CC[C@@H](C)C[C@H]1O1195.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-Neoisomenthol,1TMS,isomer #1CC(C)[C@H]1CC[C@@H](C)C[C@H]1O[Si](C)(C)C1244.5Semi standard non polar33892256
(+)-Neoisomenthol,1TBDMS,isomer #1CC(C)[C@H]1CC[C@@H](C)C[C@H]1O[Si](C)(C)C(C)(C)C1470.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Neoisomenthol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9500000000-a610fe2868ba87b759ee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Neoisomenthol GC-MS (1 TMS) - 70eV, Positivesplash10-01w0-9520000000-26cc8cab97979ec9fb4d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Neoisomenthol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Neoisomenthol 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 - (+)-Neoisomenthol 10V, Positive-QTOFsplash10-052r-0900000000-0c54797416987a09fdc72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 20V, Positive-QTOFsplash10-0a4r-6900000000-bd03de53003ab3ad94c32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 40V, Positive-QTOFsplash10-0a4i-9100000000-cdad8953e5a863785f4c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 10V, Negative-QTOFsplash10-0a4i-0900000000-35bb57f3b1e1db7e05312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 20V, Negative-QTOFsplash10-0a4i-0900000000-6f5b57bb56920ed10bd22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 40V, Negative-QTOFsplash10-0bvr-5900000000-291ecb7fa19007ee756b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 10V, Negative-QTOFsplash10-0a4i-0900000000-f6034c6a8245c68a37ac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 20V, Negative-QTOFsplash10-0a4i-0900000000-7efa42d43b7858e2c2ce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 40V, Negative-QTOFsplash10-0zfr-0900000000-b6eef0a7f66ac7e97e782021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 10V, Positive-QTOFsplash10-05mk-9800000000-bb8a9e58bdc61e2654e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 20V, Positive-QTOFsplash10-053e-9100000000-6405f7fe35f6f6bdc8c52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Neoisomenthol 40V, Positive-QTOFsplash10-0006-9000000000-fee5c7d55bf523973cbf2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB021834
KNApSAcK IDC00053538
Chemspider ID18159
KEGG Compound IDNot Available
BioCyc IDCPD-4945
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound19244
PDB IDNot Available
ChEBI ID18451
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1374441
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.