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Showing NP-Card for Carvyl acetate (NP0049003)

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Record Information
Version2.0
Created at2022-03-17 21:05:35 UTC
Updated at2022-03-17 21:05:36 UTC
NP-MRD IDNP0049003
Secondary Accession NumbersNone
Natural Product Identification
Common NameCarvyl acetate
DescriptionCarvyl acetate, also known as fema 2250, 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. Carvyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Carvyl acetate is a sweet, fruity, and green tasting compound. Outside of the human body, Carvyl acetate is found, on average, in the highest concentration within caraway. Carvyl acetate has also been detected, but not quantified in, a few different foods, such as celery stalks, peppermints, and wild celeries. Carvyl acetate is found in Agathosma betulina, Citrus aurantifolia , Citrus aurantium , Citrus hystrix , Citrus limon , Citrus grandis , Citrus paradisi , Citrus reticulata , Citrus sinensis , Mentha aquatica, Mentha pulegium and Santolina chamaecyparissus. This could make carvyl acetate a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049003 (Carvyl acetate)


  Mrv0541 02241216352D          

 14 14  0  0  0  0            999 V2000
   -2.9732   -3.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877   -3.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4021   -3.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1166   -3.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1167   -4.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4022   -5.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4022   -5.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6878   -6.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1167   -6.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877   -4.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4021   -2.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -3.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5443   -3.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -4.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
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3D MOL for NP0049003 (Carvyl acetate)

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3D SDF for NP0049003 (Carvyl acetate)

  Mrv0541 02241216352D          

 14 14  0  0  0  0            999 V2000
   -2.9732   -3.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877   -3.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4021   -3.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1166   -3.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1167   -4.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4022   -5.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4022   -5.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6878   -6.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1167   -6.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877   -4.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4021   -2.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -3.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5443   -3.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -4.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049003

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(CC=C1C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O2/c1-8(2)11-6-5-9(3)12(7-11)14-10(4)13/h5,11-12H,1,6-7H2,2-4H3

> <INCHI_KEY>
YTHRBOFHFYZBRJ-UHFFFAOYSA-N

> <FORMULA>
C12H18O2

> <MOLECULAR_WEIGHT>
194.2701

> <EXACT_MASS>
194.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.49853387211209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl acetate

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
2.430126995

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.013873912800801

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
57.1473

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049003 (Carvyl acetate)
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PDB for NP0049003 (Carvyl 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  O   UNK     0      -5.550  -6.480   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.884  -7.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.217  -6.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.551  -7.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.551  -8.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.217  -9.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.217 -11.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.884 -11.870   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.551 -11.870   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.884  -8.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.217  -4.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.216  -7.250   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.883  -6.480   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.216  -8.790   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6    2                                                       
CONECT   11    3                                                            
CONECT   12    1   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 NP0049003 (Carvyl acetate)
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SMILES for NP0049003 (Carvyl acetate)
CC(=O)OC1CC(CC=C1C)C(C)=C
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INCHI for NP0049003 (Carvyl acetate)
InChI=1S/C12H18O2/c1-8(2)11-6-5-9(3)12(7-11)14-10(4)13/h5,11-12H,1,6-7H2,2-4H3
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View in JSmol
Synonyms
ValueSource
Carvyl acetic acidGenerator
1-p-Mentha-6(8,9)-dien-2-yl acetateHMDB
2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, 1-acetateHMDB
2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, acetateHMDB
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-yl acetateHMDB
5-Isopropenyl-2-methyl-2-cyclohexen-1-yl acetateHMDB
5-Isopropenyl-2-methylcyclohex-2-en-1-yl acetateHMDB
6-Acetoxy-p-menta-1,8-dieneHMDB
Carveol acetateHMDB
FEMA 2250HMDB
p-Mentha-1(6),8-dien-2-yl acetateHMDB
p-Mentha-6,8-dien-2-ol, acetateHMDB
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl acetic acidGenerator
Chemical FormulaC12H18O2
Average Mass194.2701 Da
Monoisotopic Mass194.13068 Da
IUPAC Name2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl acetate
Traditional Name2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl acetate
CAS Registry Number97-42-7
SMILES
CC(=O)OC1CC(CC=C1C)C(C)=C
InChI Identifier
InChI=1S/C12H18O2/c1-8(2)11-6-5-9(3)12(7-11)14-10(4)13/h5,11-12H,1,6-7H2,2-4H3
InChI KeyYTHRBOFHFYZBRJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agathosma betulinaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Alexander J. MacLeod, Glesni MacLeod, G. Subramanian. Volatile aroma constituents of celery. Phyt...
Carum carviFooDB
Citrus aurantiifoliaPlant
Citrus aurantiumPlant
Citrus hystrixPlant
Citrus limonPlant
Citrus maximaPlant
Citrus paradisiPlant
Citrus reticulataPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
Mentha aquaticaLOTUS Database
Mentha pulegiumLOTUS Database
Mentha x piperitaFooDB
Santolina chamaecyparissusLOTUS 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
logP3.63ALOGPS
logP2.43ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.15 m³·mol⁻¹ChemAxon
Polarizability22.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038046  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017256  
KNApSAcK IDNot Available
Chemspider ID7058  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7335  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References