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Showing NP-Card for vanillyl ethyl ether (NP0327459)

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Record Information
Version2.0
Created at2022-09-12 10:03:24 UTC
Updated at2022-09-12 10:03:24 UTC
NP-MRD IDNP0327459
Secondary Accession NumbersNone
Natural Product Identification
Common Namevanillyl ethyl ether
Description4-(Ethoxymethyl)-2-methoxyphenol, also known as alpha-ethoxy-2-methoxy-p-cresol or ethyl 4-hydroxy-3-methoxybenzyl ether, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-(Ethoxymethyl)-2-methoxyphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-(Ethoxymethyl)-2-methoxyphenol is a sweet, alcoholic, and chocolate tasting compound. Outside of the human body,. vanillyl ethyl ether is found in Vanilla planifolia. 4-(Ethoxymethyl)-2-methoxyphenol is a food additive listed in the EAFUS food Additive Database (Jan 2001).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0327459 (vanillyl ethyl ether)


  Mrv0541 05061309542D          

 13 13  0  0  0  0            999 V2000
    2.1434   -2.8875    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   -2.4750    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   -1.2375    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  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  7  1  0  0  0  0
M  END
Download

3D MOL for NP0327459 (vanillyl ethyl ether)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -4.0315    1.2747   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    0.0669   -0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0360    0.0678   -0.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896   -0.9631   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477   -0.8233    0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -1.4134    1.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -1.2695    2.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062   -0.5310    1.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -0.3752    2.4273 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2711    0.0596    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3106    0.8043   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046    1.4279   -1.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084   -0.0839   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7497    2.1536   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7999    1.4631    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1157    1.0450   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9982    0.1857   -2.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104   -0.8525   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975   -1.9220   -0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9312   -0.9229   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272   -1.9956    1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618   -1.7303    3.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331   -0.7791    3.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2035    1.7549   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8317    0.7008   -2.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    2.2743   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937    0.3834   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 13  2  0
 13 10  1  0
 10 11  1  0
 11 12  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  4 19  1  0
  4 20  1  0
 13 27  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
  9 23  1  0
  7 22  1  0
  6 21  1  0
M  END
Download

3D SDF for NP0327459 (vanillyl ethyl ether)


  Mrv0541 05061309542D          

 13 13  0  0  0  0            999 V2000
    2.1434   -2.8875    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   -2.4750    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   -1.2375    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  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  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327459

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOCC1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O3/c1-3-13-7-8-4-5-9(11)10(6-8)12-2/h4-6,11H,3,7H2,1-2H3

> <INCHI_KEY>
KOCVACNWDMSLBM-UHFFFAOYSA-N

> <FORMULA>
C10H14O3

> <MOLECULAR_WEIGHT>
182.2164

> <EXACT_MASS>
182.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.986503818378782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(ethoxymethyl)-2-methoxyphenol

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.7445939196666669

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.91489707428332

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0798633661351955

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
50.81780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(ethoxymethyl)-2-methoxyphenol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0327459 (vanillyl ethyl ether)

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PDB for NP0327459 (vanillyl ethyl ether)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   12                                                            
CONECT    3    1   13                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    8   10                                                       
CONECT    7    8   13                                                       
CONECT    8    4    6    7                                                  
CONECT    9    5   10   11                                                  
CONECT   10    6    9   12                                                  
CONECT   11    9                                                            
CONECT   12    2   10                                                       
CONECT   13    3    7                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0327459 (vanillyl ethyl ether)
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SMILES for NP0327459 (vanillyl ethyl ether)
CCOCC1=CC(OC)=C(O)C=C1
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INCHI for NP0327459 (vanillyl ethyl ether)
InChI=1S/C10H14O3/c1-3-13-7-8-4-5-9(11)10(6-8)12-2/h4-6,11H,3,7H2,1-2H3
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View in JSmol
Synonyms
ValueSource
4-(Ethoxymethyl)-2-methoxy-phenolHMDB
4-(Ethoxymethyl)-2-methoxyphenol, 9ciHMDB
alpha-Ethoxy-2-methoxy-p-cresolHMDB
Ethyl 4-hydroxy-3-methoxybenzyl etherHMDB
Ethyl vanillyl etherHMDB
Vanillyl ethyl etherHMDB
Chemical FormulaC10H14O3
Average Mass182.2164 Da
Monoisotopic Mass182.09429 Da
IUPAC Name4-(ethoxymethyl)-2-methoxyphenol
Traditional Name4-(ethoxymethyl)-2-methoxyphenol
CAS Registry NumberNot Available
SMILES
CCOCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C10H14O3/c1-3-13-7-8-4-5-9(11)10(6-8)12-2/h4-6,11H,3,7H2,1-2H3
InChI KeyKOCVACNWDMSLBM-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
Vanilla planifolia Jacks.LOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassMethoxyphenols  
Direct ParentMethoxyphenols  
Alternative Parents
Substituents
  • Methoxyphenol
    • 

  • Benzylether
    • 

  • Phenoxy compound
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Anisole
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP1.8ALOGPS
logP1.74ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.82 m³·mol⁻¹ChemAxon
Polarizability19.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037641  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016757  
KNApSAcK IDNot Available
Chemspider ID55496  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61586  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]