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Showing NP-Card for p-propenylanisole (NP0262929)

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Record Information
Version2.0
Created at2022-09-08 05:56:57 UTC
Updated at2022-09-08 05:56:57 UTC
NP-MRD IDNP0262929
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-propenylanisole
DescriptionAnethole, also known as p-propenylanisole, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Anethole is an extremely weak basic (essentially neutral) compound (based on its pKa). p-propenylanisole is found in Agrimonia pilosa, Anemopsis californica, Anthriscus cerefolium, Asarum epigynum, Baccharis dracunculifolia, Basella alba, Bellis perennis, Blepharocalyx tweediei, Carum carvi, Chaerophyllum bulbosum, Chaerophyllum macrospermum, Croton sarcopetalus, Dalbergia ecastaphyllum, Erucaria microcarpa, Foeniculum vulgare, Glycyrrhiza glabra, Helichrysum arenarium, Homalomena occulta, Ifloga spicata, Illicium verum, Monopteryx uaucu, Myrtus communis, Origanum dictamnus, Osmorhiza aristata, Paullinia cupana, Pimenta racemosa, Pimpinella anisum, Polygala senega, Salvia fruticosa, Saussurea costus, Solidago odora, Stevia rebaudiana, Swertia japonica, Syzygium aromaticum, Teucrium cyprium, Thapsia garganica, Thymus vulgaris, Vitex agnus-castus, Zanthoxylum dipetalum and Zanthoxylum schinifolium. p-propenylanisole was first documented in 2014 (PMID: 24689303). A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0262929 (p-propenylanisole)


  Mrv1533004161508362D          

 11 11  0  0  0  0            999 V2000
    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 O   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    0.8250    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
    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   -1.6500    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
    0.0000    0.0000    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
  1  2  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  4  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
M  END
Download

3D MOL for NP0262929 (p-propenylanisole)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.3846    0.0210   -0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8833   -0.1578   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1258    0.5176    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6960    0.3900    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042    1.1345    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4710    1.0082    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207    0.1528    0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5035    0.0789    0.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2849   -0.7440   -0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -0.5709   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0484   -0.4633   -0.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170   -0.1350   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7776   -0.7485    0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564    1.0403   -0.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5473   -0.8645   -1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796    1.2139    1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4027    1.8126    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0615    1.5937    1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -1.7169   -0.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2039   -1.0115    0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6641   -0.2176   -1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -1.2451   -1.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849   -1.0884   -1.2210 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 NP0262929 (p-propenylanisole)


  Mrv1533004161508362D          

 11 11  0  0  0  0            999 V2000
    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 O   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    0.8250    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
    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   -1.6500    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
    0.0000    0.0000    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
  1  2  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  4  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262929

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
RUVINXPYWBROJD-UHFFFAOYSA-N

> <FORMULA>
C10H12O

> <MOLECULAR_WEIGHT>
148.205

> <EXACT_MASS>
148.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.46051546722152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methoxy-4-(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>
47.881

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-propenylanisole

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0262929 (p-propenylanisole)

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PDB for NP0262929 (p-propenylanisole)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   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
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10    3                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0262929 (p-propenylanisole)
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SMILES for NP0262929 (p-propenylanisole)
COC1=CC=C(C=CC)C=C1
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INCHI for NP0262929 (p-propenylanisole)
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3
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View in JSmol
Synonyms
ValueSource
Methyl 4-(prop-1-en-1-yl)phenyl etherChEBI
p-PropenylanisoleChEBI
1-(4-Methoxyphenyl)propeneMeSH
1-Methoxy-4-(1-propenyl)benzeneMeSH
Anethole, (e)-isomerMeSH
Anethole, (Z)-isomerMeSH
trans-AnetholeMeSH
Chemical FormulaC10H12O
Average Mass148.2050 Da
Monoisotopic Mass148.08882 Da
IUPAC Name1-methoxy-4-(prop-1-en-1-yl)benzene
Traditional Namep-propenylanisole
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=CC)C=C1
InChI Identifier
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3
InChI KeyRUVINXPYWBROJD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agrimonia pilosaLOTUS Database
Anemopsis californicaLOTUS Database
Anthriscus cerefoliumLOTUS Database
Asarum epigynumLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Basella albaLOTUS Database
Bellis perennisLOTUS Database
Blepharocalyx tweedieiLOTUS Database
Carum carviLOTUS Database
Chaerophyllum bulbosumLOTUS Database
Chaerophyllum macrospermumLOTUS Database
Croton sarcopetalusLOTUS Database
Dalbergia ecastaphyllumLOTUS Database
Erucaria microcarpaLOTUS Database
Foeniculum vulgareLOTUS Database
Glycyrrhiza glabraLOTUS Database
Helichrysum arenariumLOTUS Database
Homalomena occultaLOTUS Database
Ifloga spicataLOTUS Database
Illicium verumLOTUS Database
Monopteryx uaucuLOTUS Database
Myrtus communisLOTUS Database
Origanum dictamnusLOTUS Database
Osmorhiza aristataLOTUS Database
Paullinia cupanaLOTUS Database
Pimenta racemosaLOTUS Database
Pimpinella anisumLOTUS Database
Polygala senegaLOTUS Database
Salvia fruticosaLOTUS Database
Saussurea costusLOTUS Database
Solidago odoraLOTUS Database
Stevia rebaudianaLOTUS Database
Swertia japonicaLOTUS Database
Syzygium aromaticumLOTUS Database
Teucrium cypriumLOTUS Database
Thapsia garganicaLOTUS Database
Thymus vulgarisLOTUS Database
Vitex agnus-castusLOTUS Database
Zanthoxylum dipetalumLOTUS Database
Zanthoxylum schinifoliumLOTUS 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnethole  
METLIN IDNot Available
PubChem Compound7703  
PDB IDNot Available
ChEBI ID2716  
Good Scents IDNot Available
References
General References
  1. Hasegaw T, Seimiya H, Fujihara T, Fujiwara N, Yamada H: Aroma profile of star anise and the structure-odor relationship of anethole. Nat Prod Commun. 2014 Feb;9(2):251-6. [PubMed:24689303  ] 
  2. LOTUS database [Link]