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Showing NP-Card for para-Mentha-1,3,5,8-tetraene (NP0044988)

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Record Information
Version2.0
Created at2022-03-10 18:52:19 UTC
Updated at2022-03-10 22:30:20 UTC
NP-MRD IDNP0044988
Secondary Accession NumbersNone
Natural Product Identification
Common Namepara-Mentha-1,3,5,8-tetraene
DescriptionPara-Mentha-1,3,5,8-tetraene, also known as Dehydro-p-cymene, p-alpha-dimethyl-styrene, Habanene or p-Cymenene, belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group. Dehydro-p-cymene is biochemically a monocyclic monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Dehydro-p-cymene is a hydrophobic, neutral molecule that is insoluble in water. It exists as a clear, colorless oil. Dehydro-p-cymene has a herbaceous, leathery, peppery odor with notes of elemi oil and thyme, as well as a touch of citrus. It has an oregano, clove, basalmic, spicy taste. Dehydro-p-cymene is used as a flavoring agent for Italian dishes and for enhancing habanero spices. Dehydro-p-cymene is found in the highest concentration within star anises but it has also been detected in several different foods, such as lemons, coffee, dill, evergreen blackberries, parsley, citrus, sage, spearmint and pepper. Dehydro-p-cymene is one of more than 140 terpenes that are found in cannabis plants (PMID:6991645 ) And the combination of these terpenoids produces the skunky, fruity odor characteristic of C. Savita.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044988 (para-Mentha-1,3,5,8-tetraene)


  Mrv1652303202019002D          

 10 10  0  0  0  0            999 V2000
    0.3656    1.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3656   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483    1.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163   -1.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for NP0044988 (para-Mentha-1,3,5,8-tetraene)

     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    2.5818    1.5145    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0379    0.3552    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8932   -0.8718    0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6233    0.1734    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0946   -1.1186   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -1.2592   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769   -0.1823   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239   -0.3569   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579    1.0784   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016    1.2661   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489    1.6242    0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0314    2.4165    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9726   -1.3952   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4544   -1.5943    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062   -0.5965    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -1.9356   -0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6685   -2.2534   -0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7366   -1.2971   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8617    0.5354   -1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1285   -0.3845    0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913    1.9756   -0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1514    2.3061   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  1 11  1  0
  1 12  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
M  END
Download

3D SDF for NP0044988 (para-Mentha-1,3,5,8-tetraene)


  Mrv1652303202019002D          

 10 10  0  0  0  0            999 V2000
    0.3656    1.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3656   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483    1.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163   -1.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0044988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3

> <INCHI_KEY>
MMSLOZQEMPDGPI-UHFFFAOYSA-N

> <FORMULA>
C10H12

> <MOLECULAR_WEIGHT>
132.2023

> <EXACT_MASS>
132.093900384

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.352834196708212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-4-(prop-1-en-2-yl)benzene

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
3.522763878333333

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
45.067499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-4-(prop-1-en-2-yl)benzene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0044988 (para-Mentha-1,3,5,8-tetraene)

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PDB for NP0044988 (para-Mentha-1,3,5,8-tetraene)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.682   2.276   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.682   1.517   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.682   0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.682  -0.758   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.049   0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.049   1.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.263   2.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.897  -2.276   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.897  -0.758   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.263   0.001   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    3    8   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0044988 (para-Mentha-1,3,5,8-tetraene)
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SMILES for NP0044988 (para-Mentha-1,3,5,8-tetraene)
CC(=C)C1=CC=C(C)C=C1
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INCHI for NP0044988 (para-Mentha-1,3,5,8-tetraene)
InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3
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Synonyms
ValueSource
1-Isopropenyl-4-methylbenzeneHMDB
1-Methyl-4-(1-methylethenyl)-benzeneHMDB
1-Methyl-4-(1-methylethenyl)benzeneHMDB
1-Methyl-4-(1-methylethenyl)benzene, 9ciHMDB
1-Methyl-4-isopropenylbenzeneHMDB
1-Methyl-4alpha-methylstyreneHMDB
2-(4-Methylphenyl)propeneHMDB
2-(p-Methylphenyl)propeneHMDB
2-p-TolylpropeneHMDB
4-IsopropenyltolueneHMDB
4-Methyl-alpha-methylstyreneHMDB
4-MethylisopropenylbenzeneHMDB
alpha,4-DimethylstyreneHMDB
alpha,p-DimethylstyreneHMDB
alpha-Dimethyl-p-styreneHMDB
alpha-Methyl-p-methylstyreneHMDB
alpha-p DimethylstyreneHMDB
CymeneneHMDB
Dehydro-p-cymeneHMDB
FEMA 3144HMDB
Ghl.PD_Mitscher_leg0.317HMDB
Isopropenyl toluene cHMDB
Methyl-4-(1-methylethenyl)-benzeneHMDB
Methyl-p-isopropenylbenzeneHMDB
p,a-Dimethylstyrene, 8ciHMDB
p,alpha-Dimethyl-styreneHMDB
p,alpha-DimethylstyreneHMDB
p,alpha-DimethylstyrolHMDB
p-alpha-Dimethyl-styreneHMDB
p-alpha-DimethylstyreneHMDB
p-CymeneneHMDB
p-Isopropenyl tolueneHMDB
p-IsopropenyltolueneHMDB
p-Methyl-alpha-methylstyreneHMDB
Para- alpha-dimethylstyreneHMDB
Chemical FormulaC10H12
Average Mass132.2023 Da
Monoisotopic Mass132.09390 Da
IUPAC Name1-methyl-4-(prop-1-en-2-yl)benzene
Traditional Name1-methyl-4-(prop-1-en-2-yl)benzene
CAS Registry Number1195-32-0
SMILES
CC(=C)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3
InChI KeyMMSLOZQEMPDGPI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Callitropsis nootkatensisLOTUS Database
Cannabis sativaNULL
      Not Available
Chamaecyparis-
Chamaecyparis sp.Plant
Citrus ×limon (L.) Burm. f. (pro sp.)-
Citrus limonPlant
Citrus reticulataPlant
Citrus sp.Plant
Daucus carotaLOTUS Database
Eucalyptus-
Eucalyptus spp.Plant
Feijoa sellowianaPlant
Juniperus-
Juniperus sp.Plant
Ligusticum sinenseLOTUS Database
Mentha rotundifoliaLOTUS Database
Penicillium expansumFungi
Petroselinum crispumLOTUS Database
Phagnalon sordidumPlant
Rhaponticum carthamoidesPlant
Ribes sp.Plant
Ribes spp.Plant
Salvia rosmarinusPlant
Thymus broussonettiPlant
Thymus maroccanusPlant
Thymus praecosPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassPhenylpropenes  
Direct ParentPhenylpropenes  
Alternative Parents
Substituents
  • Phenylpropene
    • 

  • Styrene
    • 

  • Toluene
    • 

  • Aromatic hydrocarbon
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic 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
logP3.79ALOGPS
logP3.52ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.07 m³·mol⁻¹ChemAxon
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029641  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000812  
KNApSAcK IDC00010905  
Chemspider ID56173  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62385  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References