Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:16:24 UTC

Update Date

2021-09-23 06:16:25 UTC

HMDB ID

HMDB0302072

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methyl ferulate

Description

Methyl ferulate, also known as methyl ferulic acid, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Methyl ferulate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Methyl ferulate can be found in garden onion, which makes methyl ferulate a potential biomarker for the consumption of this food product.

Structure

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


  Mrv0541 02241220572D          

 15 15  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   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
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    0.7145    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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 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
    0.0000    0.8250    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
  3  4  1  0  0  0  0
  5  2  1  4  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  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302072

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C=CC1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3

> <INCHI_KEY>
AUJXJFHANFIVKH-UHFFFAOYSA-N

> <FORMULA>
C11H12O4

> <MOLECULAR_WEIGHT>
208.2106

> <EXACT_MASS>
208.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.28948529038975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
2.054077062

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.86784918730006

> <JCHEM_PKA_STRONGEST_BASIC>
-4.888620088905742

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
56.273100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    7                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0302072
HETATM    1  C1  UNL     1       5.620   0.024  -1.268  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.484  -0.338  -0.527  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.244   0.091  -0.947  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.111   0.797  -1.974  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.023  -0.268  -0.198  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.866   0.144  -0.607  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.374  -0.171   0.081  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.436  -0.930   1.223  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.637  -1.219   1.866  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.790  -0.720   1.326  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.018  -0.963   1.906  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.792   0.058   0.168  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.992   0.542  -0.340  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.941   1.326  -1.516  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.588   0.316  -0.429  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.368   0.506  -2.241  1.00  0.00           H  
HETATM   17  H2  UNL     1       6.311  -0.809  -1.460  1.00  0.00           H  
HETATM   18  H3  UNL     1       6.181   0.797  -0.665  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.135  -0.864   0.670  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.809   0.761  -1.515  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.504  -1.313   1.627  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.615  -1.818   2.753  1.00  0.00           H  
HETATM   23  H8  UNL     1      -4.063  -1.522   2.745  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.203   2.129  -1.343  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.945   1.813  -1.611  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.705   0.710  -2.422  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.556   0.921  -1.335  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   19
CONECT    6    7   20
CONECT    7    8    8   15
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   12
CONECT   11   23
CONECT   12   13   15   15
CONECT   13   14
CONECT   14   24   25   26
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator
Methyl ferulic acid	Generator

Chemical Formula

C₁₁H₁₂O₄

Average Molecular Weight

208.2106

Monoisotopic Molecular Weight

208.073558872

IUPAC Name

methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C=CC1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3

InChI Key

AUJXJFHANFIVKH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302072)

Food

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

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	1.86	ALOGPS
logP	2.05	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.87	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	56.27 m³·mol⁻¹	ChemAxon
Polarizability	21.29 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]+	145.842	32859911
AllCCS	[M+H-H2O]+	141.762	32859911
AllCCS	[M+Na]+	150.732	32859911
AllCCS	[M+NH4]+	149.639	32859911
AllCCS	[M-H]-	146.062	32859911
AllCCS	[M+Na-2H]-	146.547	32859911
AllCCS	[M+HCOO]-	147.173	32859911
DeepCCS	[M+H]+	148.328	30932474
DeepCCS	[M-H]-	145.97	30932474
DeepCCS	[M-2H]-	179.772	30932474
DeepCCS	[M+Na]+	154.558	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.3321 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.86 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1832.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	313.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	180.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	471.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	412.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1078.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	383.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1044.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	255.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	360.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	261.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.7 seconds	40023050

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 - Methyl ferulate 10V, Positive-QTOF	splash10-056r-0950000000-5bf20a90acfb2f98ec03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 20V, Positive-QTOF	splash10-056s-1930000000-a850f9d9300e56741a65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 40V, Positive-QTOF	splash10-054k-3900000000-d64fafa881d4ae0f3e4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 10V, Negative-QTOF	splash10-0a4i-0590000000-d66fecbfc6fbc59870b3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 20V, Negative-QTOF	splash10-0a6r-0940000000-c274326ebb66f16767a6	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 40V, Negative-QTOF	splash10-08gj-1900000000-8ce1f8bc342d3594e4b8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 10V, Positive-QTOF	splash10-0570-0920000000-48494f23861a85a28046	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 20V, Positive-QTOF	splash10-0a71-0910000000-6661560529ed58410fa6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 40V, Positive-QTOF	splash10-016s-5900000000-c255cecf26dba479761c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 10V, Negative-QTOF	splash10-056r-0950000000-d2c9649e2c66a291c741	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 20V, Negative-QTOF	splash10-001i-0900000000-3e2b5e16597f12bbdc90	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl ferulate 40V, Negative-QTOF	splash10-053r-2900000000-aa2c56ed02382f1a3b23	2021-10-21	Wishart Lab	View Spectrum

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

FDB001823

KNApSAcK ID

Not Available

Chemspider ID

15949

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16830

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 Methyl ferulate (HMDB0302072)

MOL for HMDB0302072 (Methyl ferulate)

3D MOL for HMDB0302072 (Methyl ferulate)

3D SDF for HMDB0302072 (Methyl ferulate)

3D-SDF for HMDB0302072 (Methyl ferulate)

PDB for HMDB0302072 (Methyl ferulate)

3D PDB for HMDB0302072 (Methyl ferulate)

SMILES for HMDB0302072 (Methyl ferulate)

INCHI for HMDB0302072 (Methyl ferulate)

Structure for HMDB0302072 (Methyl ferulate)

3D Structure for HMDB0302072 (Methyl ferulate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra