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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 05:36:06 UTC

Update Date

2021-09-24 05:36:06 UTC

HMDB ID

HMDB0303913

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-hydroxy-3-methoxybenzoic acid ethyl ester

Description

Ethyl vanillate belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Based on a literature review very few articles have been published on Ethyl vanillate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1533004191520282D          

 14 14  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   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
    1.4289    2.4750    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 O   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 O   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
    0.0000    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  6 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303913

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-3-14-10(12)7-4-5-8(11)9(6-7)13-2/h4-6,11H,3H2,1-2H3

> <INCHI_KEY>
MWAYRGBWOVHDDZ-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.202

> <EXACT_MASS>
196.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.837761328321506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
1.8722941473333332

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.994151680626729

> <JCHEM_PKA_STRONGEST_BASIC>
-4.897002122532112

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
51.27600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   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       2.667  -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  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  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                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    6                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0303913
HETATM    1  C1  UNL     1       4.143   1.150   0.576  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.829  -0.042  -0.269  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.535  -0.579   0.018  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.377   0.150  -0.129  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.486   1.335  -0.532  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.068  -0.444   0.178  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.036  -1.744   0.619  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.250  -2.324   0.914  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.380  -1.568   0.756  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.596  -2.192   1.065  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.315  -0.269   0.319  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.504   0.418   0.189  1.00  0.00           O  
HETATM   13  C9  UNL     1      -3.631   1.741  -0.241  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.085   0.295   0.029  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.259   1.278   0.561  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.829   0.971   1.615  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.695   2.084   0.213  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.554  -0.847  -0.008  1.00  0.00           H  
HETATM   19  H5  UNL     1       3.949   0.167  -1.347  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.870  -2.326   0.737  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.267  -3.346   1.255  1.00  0.00           H  
HETATM   22  H8  UNL     1      -4.430  -1.660   0.958  1.00  0.00           H  
HETATM   23  H9  UNL     1      -4.615   1.938  -0.728  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.527   2.496   0.556  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.867   2.006  -1.027  1.00  0.00           H  
HETATM   26  H12 UNL     1      -1.089   1.314  -0.310  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   14
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   11
CONECT   10   22
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   23   24   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl vanillic acid	Generator
4-Hydroxy-3-methoxybenzoate ethyl ester	Generator

Chemical Formula

C₁₀H₁₂O₄

Average Molecular Weight

196.202

Monoisotopic Molecular Weight

196.073558866

IUPAC Name

ethyl 4-hydroxy-3-methoxybenzoate

Traditional Name

ethyl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C10H12O4/c1-3-14-10(12)7-4-5-8(11)9(6-7)13-2/h4-6,11H,3H2,1-2H3

InChI Key

MWAYRGBWOVHDDZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Methoxyphenol
Benzoate ester
Phenoxy compound
Anisole
Methoxybenzene
Benzoyl
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0303913)

Food

Beverage

Fermented beverage

Red wine (FooDB: FOOD00911)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.68	ALOGPS
logP	1.87	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.28 m³·mol⁻¹	ChemAxon
Polarizability	19.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	142.634	32859911
AllCCS	[M+H-H2O]+	138.519	32859911
AllCCS	[M+Na]+	147.567	32859911
AllCCS	[M+NH4]+	146.464	32859911
AllCCS	[M-H]-	143.02	32859911
AllCCS	[M+Na-2H]-	143.719	32859911
AllCCS	[M+HCOO]-	144.568	32859911
DeepCCS	[M+H]+	142.392	30932474
DeepCCS	[M-H]-	139.776	30932474
DeepCCS	[M-2H]-	175.455	30932474
DeepCCS	[M+Na]+	150.994	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 10V, Positive-QTOF	splash10-0002-0900000000-d2daacd55e408efdd25e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 20V, Positive-QTOF	splash10-0uka-0900000000-3f082bbda73fb9e0e1ae	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 40V, Positive-QTOF	splash10-0fk9-7900000000-1d360f98a67aa873fa57	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 10V, Negative-QTOF	splash10-0002-0900000000-bfa5e7cb93f7fb6d4071	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 20V, Negative-QTOF	splash10-0002-0900000000-303e3d5c9b0a2ee21212	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 40V, Negative-QTOF	splash10-0pba-5900000000-8950bca6054650547018	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 10V, Positive-QTOF	splash10-0udj-0900000000-e6c821dac0ffb01a0f25	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 20V, Positive-QTOF	splash10-0udi-1900000000-3e4a2d24633eb693d61b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 40V, Positive-QTOF	splash10-0udi-9600000000-46e6bddfca0447daa783	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 10V, Negative-QTOF	splash10-0002-0900000000-27fe388f1ee731580190	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 20V, Negative-QTOF	splash10-0uka-0900000000-1344d138832ff000320f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-methoxybenzoic acid ethyl ester 40V, Negative-QTOF	splash10-0a4l-9700000000-f8e06eff370b34750cf6	2021-10-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029772

KNApSAcK ID

C00030768

Chemspider ID

11541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12038

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 4-hydroxy-3-methoxybenzoic acid ethyl ester (HMDB0303913)

MOL for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

3D MOL for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

3D SDF for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

3D-SDF for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

PDB for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

3D PDB for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

SMILES for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

INCHI for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

Structure for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

3D Structure for HMDB0303913 (4-hydroxy-3-methoxybenzoic acid ethyl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra

NMR Spectra