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Showing NP-Card for p-Menth-1-en-9-ol acetate (NP0048720)

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Record Information
Version2.0
Created at2022-03-17 21:01:08 UTC
Updated at2022-03-17 21:01:08 UTC
NP-MRD IDNP0048720
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Menth-1-en-9-ol acetate
DescriptionP-Menth-1-en-9-ol acetate, also known as 9-acetoxy-1-p-menthene, 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-9-ol acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). P-Menth-1-en-9-ol acetate is a fruity, herbal, and spicy tasting compound. Outside of the human body, p-Menth-1-en-9-ol acetate has been detected, but not quantified in, mandarin orange (clementine, tangerine) and spearmints. p-Menth-1-en-9-ol acetate is found in Agathosma betulina. This could make p-menth-1-en-9-ol acetate a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048720 (p-Menth-1-en-9-ol acetate)


  Mrv0541 05061309412D          

 14 14  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
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3D MOL for NP0048720 (p-Menth-1-en-9-ol acetate)

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3D SDF for NP0048720 (p-Menth-1-en-9-ol acetate)

  Mrv0541 05061309412D          

 14 14  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(COC(C)=O)C1CCC(C)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2/c1-9-4-6-12(7-5-9)10(2)8-14-11(3)13/h4,10,12H,5-8H2,1-3H3

> <INCHI_KEY>
QUHIXSUMNSRNNP-UHFFFAOYSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.286

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.338626379742486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)propyl acetate

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
2.6498589863333324

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.994419595157071

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
57.70600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)propyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048720 (p-Menth-1-en-9-ol acetate)
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PDB for NP0048720 (p-Menth-1-en-9-ol acetate)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8   10   14                                                       
CONECT    9    1    4    5                                                  
CONECT   10    2    8   12                                                  
CONECT   11    3   13   14                                                  
CONECT   12    6    7   10                                                  
CONECT   13   11                                                            
CONECT   14    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0048720 (p-Menth-1-en-9-ol acetate)
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SMILES for NP0048720 (p-Menth-1-en-9-ol acetate)
CC(COC(C)=O)C1CCC(C)=CC1
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INCHI for NP0048720 (p-Menth-1-en-9-ol acetate)
InChI=1S/C12H20O2/c1-9-4-6-12(7-5-9)10(2)8-14-11(3)13/h4,10,12H,5-8H2,1-3H3
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Synonyms
ValueSource
p-Menth-1-en-9-ol acetic acidGenerator
1-p-Menthen-9-yl acetateHMDB
3-Cyclohexene-1-ethanol, beta,4-dimethyl-, acetateHMDB
9-Acetoxy-1-p-mentheneHMDB
beta,4-Dimethyl-3-cyclohexene-1-ethyl acetateHMDB
beta,4-Dimethylcyclohex-3-ene-1-ethyl acetateHMDB
p-Ment-1-en-9-ol acetateHMDB
p-Menth-1-en-9-ol, acetateHMDB
p-Menth-1-en-9-yl acetateHMDB
2-(4-Methylcyclohex-3-en-1-yl)propyl acetic acidGenerator
Chemical FormulaC12H20O2
Average Mass196.2860 Da
Monoisotopic Mass196.14633 Da
IUPAC Name2-(4-methylcyclohex-3-en-1-yl)propyl acetate
Traditional Name2-(4-methylcyclohex-3-en-1-yl)propyl acetate
CAS Registry Number28839-13-6
SMILES
CC(COC(C)=O)C1CCC(C)=CC1
InChI Identifier
InChI=1S/C12H20O2/c1-9-4-6-12(7-5-9)10(2)8-14-11(3)13/h4,10,12H,5-8H2,1-3H3
InChI KeyQUHIXSUMNSRNNP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agathosma betulinaLOTUS Database
Citrus reticulataFooDB
Mentha spicataFooDB
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
logP3.75ALOGPS
logP2.65ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.71 m³·mol⁻¹ChemAxon
Polarizability23.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037301  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016320  
KNApSAcK IDNot Available
Chemspider ID459499  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound527144  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References