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Showing NP-Card for trans-Anethol (NP0045014)

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Record Information
Version2.0
Created at2022-03-10 18:52:45 UTC
Updated at2022-03-10 22:22:37 UTC
NP-MRD IDNP0045014
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-Anethol
DescriptionTrans-Anethole, also known as E-Anethole, Anise camphor or simply Anethole belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. It is also classified as a phenylpropene. There are two known Anethole isomers including Trans- and Cis-anethole. The more abundant isomer, and the one preferred for use, is the trans or E isomer. Trans-Anethole is a neutral, hydrophobic molecule that is not water soluble. Anethole has a sweet, anise, licorice aroma. Anethole is distinctly sweet, measuring 13 times sweeter than sugar. It is perceived as being pleasant to the taste even at higher concentrations. It is used in alcoholic drinks ouzo, rakı, anisette and absinthe, among others. It is also used in seasoning and confectionery applications, oral hygiene products, and in small quantities in natural berry flavors. It is a widely used food additive and fragrance agent. Anethole is found in a number of different foods and spices such as anises, star anises, fennels sweet basils, dills, and sweet marjorams. Anethole has also been detected, but not quantified in, common oregano, cumins, white mustards, pepper (spice), and caraway. Trans-Anethole is also one of many non-cannabinoid phenols that are found in cannabis plants (PMID: 6991645 ). Anethole has potent antimicrobial, nematicidal and antifungal activities (PMID:11807977 , 17078111 , 18944489 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045014 (trans-Anethol)


  Mrv1652309272007292D          

 11 11  0  0  0  0            999 V2000
10001.127210000.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.842010000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.556810000.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2737 9999.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4231 9999.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.416110000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.701610000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.987110000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9870 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7015 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4161 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
  1  6  1  0  0  0  0
  9  4  1  0  0  0  0
M  END
Download

3D MOL for NP0045014 (trans-Anethol)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -4.4194   -0.0337    0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9420    0.2576    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0554   -0.6862   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.5016   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036    0.7013    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3746    0.8415    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1517   -0.2724   -0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5374   -0.1743   -0.1156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120    1.0426    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5790   -1.4889   -0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1959   -1.5834   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8667    0.2060   -0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8841    0.6395    0.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -1.1051    0.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677    1.2495    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884   -1.6821   -0.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    1.5819    0.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    1.8061    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798    1.6265    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840    0.8230    0.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461    1.6702   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -2.3604   -0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376   -2.5576   -0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  4 11  1  0
 11 10  2  0
 10  7  1  0
  9 19  1  0
  9 20  1  0
  9 21  1  0
  6 18  1  0
  5 17  1  0
  3 16  1  0
  2 15  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
 11 23  1  0
 10 22  1  0
M  END
Download

3D SDF for NP0045014 (trans-Anethol)


  Mrv1652309272007292D          

 11 11  0  0  0  0            999 V2000
10001.127210000.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.842010000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.556810000.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2737 9999.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4231 9999.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.416110000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.701610000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.987110000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9870 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7015 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4161 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
  1  6  1  0  0  0  0
  9  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045014

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(\C=C\C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+

> <INCHI_KEY>
RUVINXPYWBROJD-ONEGZZNKSA-N

> <FORMULA>
C10H12O

> <MOLECULAR_WEIGHT>
148.205

> <EXACT_MASS>
148.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.459332423778438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methoxy-4-[(1E)-prop-1-en-1-yl]benzene

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
2.9389116129999997

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.822404266999745

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
47.88100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anethole

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0045014 (trans-Anethol)

Download
PDB for NP0045014 (trans-Anethol)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.7718668.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.1058667.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8671.4398668.205   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8663.4448665.129   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8661.8568666.048   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.4438667.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.1108668.207   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.7768667.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.7768665.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.1098665.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.4438665.897   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    5    9                                                       
CONECT    5    4                                                            
CONECT    6    7   11    1                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    4                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0045014 (trans-Anethol)
Download
SMILES for NP0045014 (trans-Anethol)
COC1=CC=C(\C=C\C)C=C1
Download
INCHI for NP0045014 (trans-Anethol)
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
Download
View in JSmol
Synonyms
ValueSource
(e)-1-(4-Methoxyphenyl)propeneChEBI
(e)-1-Methoxy-4-(1-propenyl)benzeneChEBI
(e)-AnetholeChEBI
(e)-p-PropenylanisoleChEBI
trans-4-(1-Propenyl)anisoleChEBI
trans-p-Methoxy-beta-methylstyreneChEBI
t-AnetholeKegg
trans-AnetholeKegg
trans-p-Methoxy-b-methylstyreneGenerator
trans-p-Methoxy-β-methylstyreneGenerator
Anethole, (Z)-isomerMeSH
1-Methoxy-4-(1-propenyl)benzeneMeSH
Anethole, (e)-isomerMeSH
p-PropenylanisoleMeSH
1-(4-Methoxyphenyl)propeneMeSH
1-Methoxy-4-(1E)-1-propen-1-ylbenzenePhytoBank
(E)-1-p-MethoxyphenylpropenePhytoBank
(E)-AnetholPhytoBank
1-Methoxy-4-[(1E)-1-propenyl]benzenePhytoBank
trans-1-(4-Methoxyphenyl)-1-propenePhytoBank
trans-1-(p-Methoxyphenyl)-1-propenePhytoBank
trans-1-(p-Methoxyphenyl)propenePhytoBank
trans-1-p-AnisylpropenePhytoBank
trans-AnetholPhytoBank
trans-p-AnetholePhytoBank
1-Methoxy-4-(1-propen-1-yl)benzenePhytoBank
1-Methoxy-4-propenylbenzenePhytoBank
1-Propene, 1-(4-methoxyphenyl)-PhytoBank
4-(1-Propenyl)anisolePhytoBank
4-(Propen-1-yl)anisolePhytoBank
4-Methoxy-1-propenylbenzenePhytoBank
4-MethoxypropenylbenzenePhytoBank
4-PropenylanisolePhytoBank
AnetholPhytoBank
AnetholePhytoBank
Anise camphorPhytoBank
IsoestragolePhytoBank
p-1-PropenylanisolePhytoBank
p-AnetholePhytoBank
p-Methoxy-beta-methylstyrenePhytoBank
p-Methoxy-β-methylstyrenePhytoBank
p-Propenylphenyl methyl etherPhytoBank
Chemical FormulaC10H12O
Average Mass148.2050 Da
Monoisotopic Mass148.08882 Da
IUPAC Name1-methoxy-4-[(1E)-prop-1-en-1-yl]benzene
Traditional Nameanethole
CAS Registry Number12002-40-3
SMILES
COC1=CC=C(\C=C\C)C=C1
InChI Identifier
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
InChI KeyRUVINXPYWBROJD-ONEGZZNKSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
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
Achillea abrotanoidesLOTUS Database
Agastache foeniculumLOTUS Database
Anemopsis californicaLOTUS Database
Anethum foeniculumPlant
Anthriscus cerefoliumLOTUS Database
Artemisia annuaPlant
Asarum epigynumLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Backhousia anisataLOTUS Database
Basella albaLOTUS Database
Bellis perennisLOTUS Database
Blepharocalyx tweedieiLOTUS Database
Cannabis sativaNULL
      Not Available
Chaerophyllum bulbosumLOTUS Database
Chaerophyllum macrospermumLOTUS Database
Chamaecyparis lawsonianaLOTUS Database
Clausena anisataLOTUS Database
Clausena heptaphyllaLOTUS Database
Croton sarcopetalusLOTUS Database
Cryptomeria japonicaLOTUS Database
Dalbergia ecastaphyllumLOTUS Database
Erucaria microcarpaLOTUS Database
Eryngium foetidumLOTUS Database
Foeniculum vulgareLOTUS Database
Ganoderma lucidumFungi
Gundelia tournefortiiLOTUS Database
Hamamelis virginianaLOTUS Database
Helichrysum arenariumLOTUS Database
Hexalobus monopetalusLOTUS Database
Homalomena occultaLOTUS Database
Ifloga spicataLOTUS Database
Illicium micranthumLOTUS Database
Illicium verumLOTUS Database
Magnolia salicifoliaLOTUS Database
Monopteryx uaucuLOTUS Database
Myristica fragransLOTUS Database
Myrrhis odorataLOTUS Database
Myrtus communisLOTUS Database
Nigella sativaLOTUS Database
Ocimum basilicumLOTUS Database
Ocimum tenuiflorumLOTUS Database
Origanum adanenseLOTUS Database
Origanum dictamnusLOTUS Database
Osmorhiza aristataLOTUS Database
Passiflora incarnataLOTUS Database
Paullinia cupanaLOTUS Database
Pimenta racemosaLOTUS Database
Pimpinella anisumLOTUS Database
Piper regnelliiLOTUS Database
Platostoma africanumLOTUS Database
Polygala senegaLOTUS Database
Porophyllum ruderaleLOTUS Database
Salvia fruticosaLOTUS Database
Scandix australisLOTUS Database
Senna alexandrinaLOTUS Database
Sinapis albaPlant
Solidago odoraLOTUS Database
Stevia rebaudianaLOTUS Database
Swertia japonicaLOTUS Database
Tagetes filifoliaLOTUS Database
Tagetes lucidaLOTUS Database
Thapsia garganicaLOTUS Database
Thymus vulgarisLOTUS Database
Trachyspermum ammiLOTUS Database
Vitex agnus-castusLOTUS Database
Zanthoxylum dipetalumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenol ethers  
Sub ClassAnisoles  
Direct ParentAnisoles  
Alternative Parents
Substituents
  • Phenoxy compound
    • 

  • Methoxybenzene
    • 

  • Styrene
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • 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
logP3.4ALOGPS
logP2.94ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.88 m³·mol⁻¹ChemAxon
Polarizability17.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002713  
Chemspider IDNot Available
KEGG Compound IDC10428  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnethole  
METLIN IDNot Available
PubChem Compound637563  
PDB IDNot Available
ChEBI ID35616  
Good Scents IDNot Available
References
General References
  1. De M, De AK, Sen P, Banerjee AB: Antimicrobial properties of star anise (Illicium verum Hook f). Phytother Res. 2002 Feb;16(1):94-5. doi: 10.1002/ptr.989. [PubMed:11807977  ] 
  2. Fujita K, Fujita T, Kubo I: Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent. Phytother Res. 2007 Jan;21(1):47-51. doi: 10.1002/ptr.2016. [PubMed:17078111  ] 
  3. Oka Y, Nacar S, Putievsky E, Ravid U, Yaniv Z, Spiegel Y: Nematicidal activity of essential oils and their components against the root-knot nematode. Phytopathology. 2000 Jul;90(7):710-5. doi: 10.1094/PHYTO.2000.90.7.710. [PubMed:18944489  ]