Showing Compound Card for (+)-Neomenthol (CDB005275)

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Record Information
Version1.0
Created at2020-04-17 19:26:52 UTC
Updated at2020-12-07 19:11:53 UTC
CannabisDB IDCDB005275
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(+)-Neomenthol
Description(+)-Neomenthol, also known as fema 2666, 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, (+)-neomenthol is considered to be an isoprenoid lipid molecule (+)-Neomenthol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (+)-Neomenthol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(1S,2S,5R)-(+)-NeomentholHMDB
(1S,2S,5R)-2-Isopropyl-5-methylcyclohexanolHMDB
(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexan-1-olHMDB
(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanolHMDB
D-NeomentholHMDB
FEMA 2666HMDB
Chemical FormulaC10H20O
Average Molecular Weight156.27
Monoisotopic Molecular Weight156.1514
IUPAC Name(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
Traditional Name(+)-neomenthol
CAS Registry Number2216-52-6
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-UTLUCORTSA-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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-22 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability19.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-Neomenthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9500000000-a610fe2868ba87b759eeSpectrum
Predicted GC-MS(+)-Neomenthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01w0-9520000000-26cc8cab97979ec9fb4dSpectrum
Predicted GC-MS(+)-Neomenthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-fc39fb91c62eb627e3af2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-5900000000-839aa9da0c06f6d099682015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-9200000000-e9b33e704445c7e908ec2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3a700dc611fb070e6b452015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-5a80eb79e919e06fa63a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-7900000000-67a39bf95581e52cb9312015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mk-9800000000-bb8a9e58bdc61e2654e62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053e-9100000000-6405f7fe35f6f6bdc8c52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-fee5c7d55bf523973cbf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-f6034c6a8245c68a37ac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-7efa42d43b7858e2c2ce2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-0900000000-b6eef0a7f66ac7e97e782021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035763
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014500
KNApSAcK IDC00053546
Chemspider ID388397
KEGG Compound IDC00553
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439263
PDB IDNot Available
ChEBI ID15402
References
General ReferencesNot Available