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Showing NP-Card for Methyl isoeugenol (NP0045162)

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Record Information
Version2.0
Created at2022-03-10 18:59:01 UTC
Updated at2022-03-10 22:21:45 UTC
NP-MRD IDNP0045162
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl isoeugenol
DescriptionMethyl isoeugenol belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying two methoxy groups. Methyl isoeugenol also belongs to the class of organic compounds known as phenyl propanoid. Methylisoeugenol is a mild, bitter, and clove tasting compound. It is the methyl ether derivative of isoeugenol, found in certain essential oils. Methyl Isoeugenol is naturally occurring and found in the essential oils of plants such as nutmegs, star anises, and gingers, ajowan caraway and allspice (PMID: 19259498 ). It can occur as both (E)- and (Z)-isomers. It has also been detected, but not quantified, in several different foods, such as sweet basils, carrots, ceylon cinnamons, wild carrots, and tarragons. Methylisoeugenol has also been reported to be a volatile component in cannabis samples (PMID: 26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045162 (Methyl isoeugenol)


  Mrv1652303202019012D          

 13 13  0  0  0  0            999 V2000
   -0.7145   -1.2375    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    1.4289    0.0000    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  2  1  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 13 11  1  0  0  0  0
M  END
Download

3D MOL for NP0045162 (Methyl isoeugenol)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    3.8033   -0.5263   -0.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4448    0.7968    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2231    1.1551    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317    0.3937    0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8851   -0.9397    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3917   -1.5086   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477   -0.7830   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014   -1.3242   -0.2021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0945   -2.6713   -0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3861    0.5717    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245    1.3631    0.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863    2.7545    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580    1.1562    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8948   -0.4501   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -1.2389    0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758   -0.8008   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889    1.5206    0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1232    2.1908    0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7233   -1.6024    0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4501   -2.5791   -0.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4512   -3.3252    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0664   -2.9806   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1767   -2.8128   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9220    2.9875    1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795    3.2532    0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    3.1497   -0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0869    2.2498    0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
  3 18  1  0
  2 17  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 19  1  0
  6 20  1  0
M  END
Download

3D SDF for NP0045162 (Methyl isoeugenol)


  Mrv1652303202019012D          

 13 13  0  0  0  0            999 V2000
   -0.7145   -1.2375    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    1.4289    0.0000    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  2  1  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 13 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C(\C=C/C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-

> <INCHI_KEY>
NNWHUJCUHAELCL-PLNGDYQASA-N

> <FORMULA>
C11H14O2

> <MOLECULAR_WEIGHT>
178.2277

> <EXACT_MASS>
178.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.923173441416182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
2.781240347333333

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.591810561844535

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
54.34420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z)-methyl isoeugenol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045162 (Methyl isoeugenol)

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PDB for NP0045162 (Methyl isoeugenol)
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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    1    5                                                       
CONECT    5    4    9                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8    9   11                                                       
CONECT    9    5    6    8                                                  
CONECT   10    7   11   12                                                  
CONECT   11    8   10   13                                                  
CONECT   12    2   10                                                       
CONECT   13    3   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0045162 (Methyl isoeugenol)
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SMILES for NP0045162 (Methyl isoeugenol)
COC1=C(OC)C=C(\C=C/C)C=C1
Download
INCHI for NP0045162 (Methyl isoeugenol)
InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-
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Synonyms
ValueSource
(Z)-Methyl isoeugenolChEBI
cis-4-Propenyl veratroleChEBI
cis-Methyl isoeugenolChEBI
(e)-Methyl eugenolHMDB
(e)-Methyl isoeugenolHMDB
1,2-Dimethoxy-4-(1-propenyl)benzene, 9ciHMDB
1,2-Dimethoxy-4-propenyl-(e)-benzeneHMDB
1,2-Dimethoxy-4-propenyl-benzeneHMDB
1,2-Dimethoxy-4-propenylbenzeneHMDB
1,3,4-Isoeugenol methyl etherHMDB
1-(3,4-Dimethoxyphenyl)-1-propeneHMDB
1-Veratryl-1-propeneHMDB
3,4-DimethoxypropenylbenzeneHMDB
4-(1-Propenyl)veratroleHMDB
4-Propenyl-1,2-dimethoxybenzeneHMDB
4-PropenylveratroleHMDB
4-trans-PropenylveratroleHMDB
FEMA 2476HMDB
Isoeugenol methyl etherHMDB
Isoeugenyl methyl etherHMDB
IsohomogenolHMDB
IsomethyleugenolHMDB
Methyl isoeugenolHMDB
O-MethylisoeugenolHMDB
trans-4-PropenylveratroleHMDB
trans-IsomethyleugenolHMDB
trans-Methyl isoeugenolHMDB
1,2-Dimethoxy-4-(1-e-propenyl)benzeneHMDB
1,2-Dimethoxy-4-(1-propenyl)benzeneHMDB
1,2-Dimethoxy-4-(1-Z-propenyl)benzeneHMDB
Isomethyleugenol, (e)-isomerHMDB
Isomethyleugenol, (Z)-isomerHMDB
MethylisoeugenolMeSH
Chemical FormulaC11H14O2
Average Mass178.2277 Da
Monoisotopic Mass178.09938 Da
IUPAC Name1,2-dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene
Traditional Name(Z)-methyl isoeugenol
CAS Registry Number6379-72-2
SMILES
COC1=C(OC)C=C(\C=C/C)C=C1
InChI Identifier
InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-
InChI KeyNNWHUJCUHAELCL-PLNGDYQASA-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
Acorus calamusLOTUS Database
Acorus gramineusLOTUS Database
Asarum europaeumLOTUS Database
Asarum rigescensLOTUS Database
Cannabis sativaNULL
      Not Available
Cinnamomum verumFooDB
Michelia albaLOTUS Database
Nicotiana alataPlant
Nicotiana bonariensisPlant
Nicotiana ingulbaPlant
Platostoma africanumLOTUS Database
Solidago odoraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassMethoxybenzenes  
Direct ParentDimethoxybenzenes  
Alternative Parents
Substituents
  • O-dimethoxybenzene
    • 

  • Dimethoxybenzene
    • 

  • Phenoxy compound
    • 

  • Styrene
    • 

  • Phenol ether
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP3.47ALOGPS
logP2.78ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.34 m³·mol⁻¹ChemAxon
Polarizability19.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041553  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021536  
KNApSAcK IDC00002760  
Chemspider ID21242881  
KEGG Compound IDC10478  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl isoeugenol  
METLIN IDNot Available
PubChem Compound1549045  
PDB IDNot Available
ChEBI ID50550  
Good Scents IDNot Available
References
General References
  1. Park IK, Kim J, Lee SG, Shin SC: Nematicidal Activity of Plant Essential Oils and Components From Ajowan (Trachyspermum ammi), Allspice (Pimenta dioica) and Litsea (Litsea cubeba) Essential Oils Against Pine Wood Nematode (Bursaphelenchus Xylophilus). J Nematol. 2007 Sep;39(3):275-9. [PubMed:19259498  ] 
  2. Cartus AT, Merz KH, Schrenk D: Metabolism of methylisoeugenol in liver microsomes of human, rat, and bovine origin. Drug Metab Dispos. 2011 Sep;39(9):1727-33. doi: 10.1124/dmd.111.038851. Epub 2011 Jun 1. [PubMed:21632962  ] 
  3. Pande C, Tewari G, Singh C, Singh S, Padalia RC: Chemical composition of the essential oil of Feronia elephantum Correa. Nat Prod Res. 2010 Nov;24(19):1807-10. doi: 10.1080/14786411003752078. [PubMed:21104525  ]