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Showing NP-Card for (±)-p-Menth-1-en-4-yl acetate (NP0049948)

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Record Information
Version2.0
Created at2022-03-17 21:20:42 UTC
Updated at2022-03-17 21:20:42 UTC
NP-MRD IDNP0049948
Secondary Accession NumbersNone
Natural Product Identification
Common Name(±)-p-Menth-1-en-4-yl acetate
Description(±)-P-Menth-1-en-4-yl acetate 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 (±)-p-Menth-1-en-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (±)-p-Menth-1-en-4-yl acetate is found, on average, in the highest concentration within nutmegs and rosemaries (±)-p-Menth-1-en-4-yl acetate has also been detected, but not quantified in, sweet marjorams and winter savories. (±)-p-Menth-1-en-4-yl acetate is found in Achillea abrotanoides, Caesulia axillaris, Curcuma pierreana, Helichrysum italicum, Mesosphaerum suaveolens, Minthostachys andina, Persea americana, Thuja occidentalis, Vitex negundo and Zanthoxylum schinifolium. This could make (±)-p-menth-1-en-4-yl acetate a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049948 ((±)-p-Menth-1-en-4-yl acetate)


  Mrv0541 02241222492D          

 14 14  0  0  0  0            999 V2000
   -3.1821   -4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -5.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -6.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -6.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -6.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -6.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532   -5.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -6.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532   -4.8911    0.0000 O   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  2  0  0  0  0
  1  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
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3D MOL for NP0049948 ((±)-p-Menth-1-en-4-yl acetate)

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3D SDF for NP0049948 ((±)-p-Menth-1-en-4-yl acetate)

  Mrv0541 02241222492D          

 14 14  0  0  0  0            999 V2000
   -3.1821   -4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -5.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -6.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -6.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -6.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -6.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532   -5.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388   -6.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532   -4.8911    0.0000 O   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  2  0  0  0  0
  1  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1(CCC(C)=CC1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2/c1-9(2)12(14-11(4)13)7-5-10(3)6-8-12/h5,9H,6-8H2,1-4H3

> <INCHI_KEY>
BFCBRSFYYLSTAA-UHFFFAOYSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.286

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.812384169434146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methyl-1-(propan-2-yl)cyclohex-3-en-1-yl acetate

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
2.7713303779999983

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.012633849484632

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
57.4594

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-isopropyl-4-methylcyclohex-3-en-1-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049948 ((±)-p-Menth-1-en-4-yl acetate)
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PDB for NP0049948 ((±)-p-Menth-1-en-4-yl acetate)
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      -5.940  -7.590   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.274  -8.360   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.274  -9.900   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.940 -10.670   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.606  -9.900   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.606  -8.360   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.940  -6.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.940 -12.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.606 -12.980   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.274 -12.980   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.606 -11.440   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.273 -10.670   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.939 -11.440   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.273  -9.130   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8   11                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0049948 ((±)-p-Menth-1-en-4-yl acetate)
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SMILES for NP0049948 ((±)-p-Menth-1-en-4-yl acetate)
CC(C)C1(CCC(C)=CC1)OC(C)=O
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INCHI for NP0049948 ((±)-p-Menth-1-en-4-yl acetate)
InChI=1S/C12H20O2/c1-9(2)12(14-11(4)13)7-5-10(3)6-8-12/h5,9H,6-8H2,1-4H3
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Synonyms
ValueSource
(±)-p-menth-1-en-4-yl acetic acidGenerator
Chemical FormulaC12H20O2
Average Mass196.2860 Da
Monoisotopic Mass196.14633 Da
IUPAC Name4-methyl-1-(propan-2-yl)cyclohex-3-en-1-yl acetate
Traditional Name1-isopropyl-4-methylcyclohex-3-en-1-yl acetate
CAS Registry Number4821-04-9
SMILES
CC(C)C1(CCC(C)=CC1)OC(C)=O
InChI Identifier
InChI=1S/C12H20O2/c1-9(2)12(14-11(4)13)7-5-10(3)6-8-12/h5,9H,6-8H2,1-4H3
InChI KeyBFCBRSFYYLSTAA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea abrotanoidesLOTUS Database
Caesulia axillarisLOTUS Database
Citrus reticulataFooDB
Curcuma pierreanaLOTUS Database
Helichrysum italicumLOTUS Database
Hyptis suaveolensLOTUS Database
Minthostachys andinaLOTUS Database
Myristica fragransFooDB
Origanum majoranaFooDB
Persea americanaLOTUS Database
Salvia rosmarinusFooDB
Satureja montanaFooDB
Thuja occidentalisLOTUS Database
Vitex negundoLOTUS Database
VitisFooDB
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
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP4.26ALOGPS
logP2.77ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.46 m³·mol⁻¹ChemAxon
Polarizability22.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062144  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021858  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20960  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available