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Showing NP-Card for p-Menth-1-en-3-ol (NP0048350)

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Record Information
Version2.0
Created at2022-03-17 20:55:05 UTC
Updated at2022-03-17 20:55:05 UTC
NP-MRD IDNP0048350
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Menth-1-en-3-ol
DescriptionPiperitol, also known as 3-carvomenthenol or fema 3179, 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. Piperitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Piperitol is a herbal tasting compound. Outside of the human body, Piperitol is found, on average, in the highest concentration within cumins. Piperitol has also been detected, but not quantified in, dills and spearmints. p-Menth-1-en-3-ol is found in Artemisia herba-alba, Asarum sieboldii, Dioscorea spongiosa, Coespeletia timotensis, Eucalyptus mitchelliana, Vitex negundo and Zanthoxylum schinifolium. This could make piperitol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048350 (p-Menth-1-en-3-ol)


  Mrv0541 02241219492D          

 11 11  0  0  0  0            999 V2000
   -0.1882    1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -0.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882   -0.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263   -0.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882    1.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6171   -0.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882   -1.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for NP0048350 (p-Menth-1-en-3-ol)

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3D SDF for NP0048350 (p-Menth-1-en-3-ol)

  Mrv0541 02241219492D          

 11 11  0  0  0  0            999 V2000
   -0.1882    1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -0.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882   -0.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263   -0.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882    1.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6171   -0.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882   -1.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC(C)=CC1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3

> <INCHI_KEY>
HPOHAUWWDDPHRS-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.05327095684219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-6-(propan-2-yl)cyclohex-2-en-1-ol

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.4146011256666675

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.763486870542224

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1526508428248317

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.141299999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-isopropyl-3-methylcyclohex-2-en-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048350 (p-Menth-1-en-3-ol)
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PDB for NP0048350 (p-Menth-1-en-3-ol)
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      -0.351   1.947   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.685   1.177   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.685  -0.363   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.351  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.982  -0.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.982   1.177   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.351   3.487   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.019  -1.133   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.351  -2.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.982  -3.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.685  -3.443   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1                                                            
CONECT    8    3                                                            
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 NP0048350 (p-Menth-1-en-3-ol)
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SMILES for NP0048350 (p-Menth-1-en-3-ol)
CC(C)C1CCC(C)=CC1O
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INCHI for NP0048350 (p-Menth-1-en-3-ol)
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3
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Synonyms
ValueSource
1-Methyl-4-isopropyl-1-cyclohexen-3-olHMDB
3-CarvomenthenolHMDB
3-Hydroxy-4-isopropyl-1-methylcyclohexeneHMDB
3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-olHMDB
3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-ol, 9ciHMDB
6-(Isopropyl)-3-methylcyclohex-2-en-1-olHMDB
6-Isopropyl-3-methyl-2-cyclohexen-1-olHMDB
FEMA 3179HMDB
Piperitol (monoterpene)HMDB
Piperitol?HMDB
Terpinen-3-olHMDB
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name3-methyl-6-(propan-2-yl)cyclohex-2-en-1-ol
Traditional Name6-isopropyl-3-methylcyclohex-2-en-1-ol
CAS Registry Number491-04-3
SMILES
CC(C)C1CCC(C)=CC1O
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3
InChI KeyHPOHAUWWDDPHRS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anethum graveolensFooDB
Artemisia herba-albaLOTUS Database
Asarum sieboldiiLOTUS Database
Cuminum cyminumFooDB
Dioscorea spongiosaLOTUS Database
Espeletia timotensisLOTUS Database
Eucalyptus mitchellianaLOTUS Database
Mentha spicataFooDB
Vitex negundoLOTUS Database
Zanthoxylum schinifoliumLOTUS 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
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP2.64ALOGPS
logP2.41ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)18.76ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.14 m³·mol⁻¹ChemAxon
Polarizability19.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035838  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014609  
KNApSAcK IDNot Available
Chemspider ID9862  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10282  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References