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Showing NP-Card for (-)-Isopulegol (NP0048445)

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Record Information
Version2.0
Created at2022-03-17 20:56:35 UTC
Updated at2025-02-11 15:48:26 UTC
NP-MRD IDNP0048445
Natural Product DOIhttps://doi.org/10.57994/2825
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Isopulegol
Description(-)-Isopulegol 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 (-)-Isopulegol is an extremely weak basic (essentially neutral) compound (based on its pKa) (-)-Isopulegol is a cooling, medicinal, and minty tasting compound. Outside of the human body, (-)-Isopulegol is found, on average, in the highest concentration within a few different foods, such as lemons, lemon balms, and rosemaries and in a lower concentration in mandarin orange (clementine, tangerine) (-)-Isopulegol has also been detected, but not quantified in, several different foods, such as lemon grass, herbs and spices, fats and oils, cornmints, and pepper (spice). (-)-Isopulegol is found in Ceratocystis coerulescens, Citrus hystrix, Clinopodium serpyllifolium, Eucalyptus brassiana, Eucalyptus citriodora , Juniperus communis, Mentha pulegium and Teucrium cyprium. This could make (-)-isopulegol a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048445 ((-)-Isopulegol)


  Mrv0541 02241219452D          

 11 11  0  0  0  0            999 V2000
   -3.3295   -3.7419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0439   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -5.3920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6150   -4.9795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6150   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9005   -5.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -6.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150   -6.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -6.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
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3D MOL for NP0048445 ((-)-Isopulegol)

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3D SDF for NP0048445 ((-)-Isopulegol)

  Mrv0541 02241219452D          

 11 11  0  0  0  0            999 V2000
   -3.3295   -3.7419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0439   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -5.3920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6150   -4.9795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6150   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9005   -5.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -6.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150   -6.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -6.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1

> <INCHI_KEY>
ZYTMANIQRDEHIO-KXUCPTDWSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.941624764523382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.316627336

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.465337368746848

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8456614349101289

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.22279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048445 ((-)-Isopulegol)
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PDB for NP0048445 ((-)-Isopulegol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.215  -6.985   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.549  -7.755   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.549  -9.295   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.215 -10.065   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.881  -9.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.881  -7.755   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.215  -5.445   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.548 -10.065   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.215 -11.605   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.881 -12.375   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.549 -12.375   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1                                                       
CONECT    7    1                                                            
CONECT    8    5                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0048445 ((-)-Isopulegol)
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SMILES for NP0048445 ((-)-Isopulegol)
C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C
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INCHI for NP0048445 ((-)-Isopulegol)
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(-)-L-IsopulegolHMDB
(1R,3R,4S)-(-)-p-Menth-8-en-3-olHMDB
5-Methyl-2-(1-methylethenyl)-(1R,2S,5R)-cyclohexanolHMDB
L-IsopulegolHMDB
IsopulegolMeSH
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
Traditional Name(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
CAS Registry Number89-79-2
SMILES
C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
InChI KeyZYTMANIQRDEHIO-KXUCPTDWSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Ceratocystis coerulescensFungi
Citrus hystrixLOTUS Database
Citrus limonFooDB
Citrus reticulataFooDB
Clinopodium serpyllifoliumLOTUS Database
Cymbopogon citratusFooDB
Eucalyptus brassianaLOTUS Database
Eucalyptus citriodoraPlant
Juniperus communisLOTUS Database
Melissa officinalis L.FooDB
Mentha arvensisFooDB
Mentha pulegiumPlant
Origanum onitesFooDB
Piper nigrum L.FooDB
Salvia rosmarinusFooDB
Teucrium cypriumLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.69ALOGPS
logP2.32ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)19.47ChemAxon
pKa (Strongest Basic)-0.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.22 m³·mol⁻¹ChemAxon
Polarizability18.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036078  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014912  
KNApSAcK IDC00010938  
Chemspider ID149356  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound170833  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References