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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:50 UTC

Update Date

2023-02-21 17:19:40 UTC

HMDB ID

HMDB0030752

Secondary Accession Numbers

HMDB30752

Metabolite Identification

Common Name

Methyl trans-p-methoxycinnamate

Description

Methyl trans-p-methoxycinnamate, also known as methyl (e)-p-methoxycinnamic acid or 4-methoxycinnamate methyl ester, belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Based on a literature review very few articles have been published on Methyl trans-p-methoxycinnamate.

Structure

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


  Mrv0541 05061305292D          

 14 14  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   -3.7125    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
    0.0000    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
    1.4289    0.8250    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
    0.0000   -1.6500    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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  2  0  0  0  0
 13  1  1  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030752

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O3/c1-13-10-6-3-9(4-7-10)5-8-11(12)14-2/h3-8H,1-2H3/b8-5+

> <INCHI_KEY>
VEZIKIAGFYZTCI-VMPITWQZSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.2112

> <EXACT_MASS>
192.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
20.727832482066365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.3576423836666662

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.819395519230252

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
54.29220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3    6    9                                                       
CONECT    4    7    9                                                       
CONECT    5    8    9                                                       
CONECT    6    3   10                                                       
CONECT    7    4   10                                                       
CONECT    8    5   11                                                       
CONECT    9    3    4    5                                                  
CONECT   10    6    7   13                                                  
CONECT   11    8   12   14                                                  
CONECT   12   11                                                            
CONECT   13    1   10                                                       
CONECT   14    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0030752
HETATM    1  C1  UNL     1      -5.467   0.681  -0.516  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.077   0.444  -0.486  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.512  -0.778  -0.808  1.00  0.00           C  
HETATM    4  O2  UNL     1      -4.293  -1.699  -1.138  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.064  -1.005  -0.771  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.224  -0.063  -0.430  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.226  -0.199  -0.366  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.960   0.906   0.016  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.331   0.880   0.107  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.973  -0.307  -0.199  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.346  -0.335  -0.108  1.00  0.00           O  
HETATM   12  C9  UNL     1       5.108   0.765   0.274  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.256  -1.420  -0.582  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.879  -1.366  -0.665  1.00  0.00           C  
HETATM   15  H1  UNL     1      -5.628   1.749  -0.226  1.00  0.00           H  
HETATM   16  H2  UNL     1      -5.930  -0.011   0.232  1.00  0.00           H  
HETATM   17  H3  UNL     1      -5.907   0.515  -1.533  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.682  -1.978  -1.032  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.662   0.908  -0.173  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.491   1.856   0.264  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.914   1.764   0.412  1.00  0.00           H  
HETATM   22  H8  UNL     1       6.182   0.508   0.267  1.00  0.00           H  
HETATM   23  H9  UNL     1       4.935   1.576  -0.480  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.796   1.203   1.253  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.738  -2.357  -0.826  1.00  0.00           H  
HETATM   26  H12 UNL     1       0.312  -2.237  -0.965  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   18
CONECT    6    7   19
CONECT    7    8    8   14
CONECT    8    9   20
CONECT    9   10   10   21
CONECT   10   11   13
CONECT   11   12
CONECT   12   22   23   24
CONECT   13   14   14   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl (e)-p-methoxycinnamate	ChEBI
Methyl (e)-p-methoxycinnamic acid	Generator
Methyl trans-p-methoxycinnamic acid	Generator
Azapeptide-based compound 42	HMDB
4-Methoxycinnamate methyl ester	HMDB
4-Methoxymethyl cinnamate	HMDB
4-Methoxycinnamate methyl ester, (Z)-isomer	HMDB
4-Methoxycinnamate methyl ester, (e)-isomer	HMDB
Methyl 4-methoxycinnamic acid	HMDB

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Weight

192.2112

Monoisotopic Molecular Weight

192.07864425

IUPAC Name

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

Traditional Name

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

CAS Registry Number

3901-07-3

SMILES

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

InChI Identifier

InChI=1S/C11H12O3/c1-13-10-6-3-9(4-7-10)5-8-11(12)14-2/h3-8H,1-2H3/b8-5+

InChI Key

VEZIKIAGFYZTCI-VMPITWQZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monomethoxybenzene (CHEBI:86901 )
alkyl cinnamate (CHEBI:86901 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030752)
Cell membrane (HMDB: HMDB0030752)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030752)

Source

Endogenous

Endogenous (HMDB: HMDB0030752)

Plant

Plant (HMDB: HMDB0030752)

Exogenous

Food

Food (HMDB: HMDB0030752)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94 - 95 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	396.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.36	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.29 m³·mol⁻¹	ChemAxon
Polarizability	20.73 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	148.157	31661259
DarkChem	[M-H]-	145.54	31661259
DeepCCS	[M+H]+	141.952	30932474
DeepCCS	[M-H]-	139.594	30932474
DeepCCS	[M-2H]-	174.23	30932474
DeepCCS	[M+Na]+	148.855	30932474
AllCCS	[M+H]+	142.1	32859911
AllCCS	[M+H-H2O]+	137.9	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	144.0	32859911
AllCCS	[M+Na-2H]-	144.7	32859911
AllCCS	[M+HCOO]-	145.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl trans-p-methoxycinnamate	COC(=O)\C=C\C1=CC=C(OC)C=C1	2630.1	Standard polar	33892256
Methyl trans-p-methoxycinnamate	COC(=O)\C=C\C1=CC=C(OC)C=C1	1578.9	Standard non polar	33892256
Methyl trans-p-methoxycinnamate	COC(=O)\C=C\C1=CC=C(OC)C=C1	1749.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl trans-p-methoxycinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-0900000000-8f58b737afca6f211acd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl trans-p-methoxycinnamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 10V, Positive-QTOF	splash10-03dl-0900000000-2e61bac3fcb144008898	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 20V, Positive-QTOF	splash10-03dl-0900000000-196c5e98469d825e719a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 40V, Positive-QTOF	splash10-01q9-2900000000-b6ee526d6735649b5e1d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 10V, Negative-QTOF	splash10-0006-0900000000-ac772984490c2b1b5064	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 20V, Negative-QTOF	splash10-052f-0900000000-8582179c9ee908abd932	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 40V, Negative-QTOF	splash10-054k-1900000000-0ab9c9b1e9c109e5e8a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 10V, Positive-QTOF	splash10-03di-0900000000-d618bd05333711a592ce	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 20V, Positive-QTOF	splash10-01qc-1900000000-364dd273e2e98bacce38	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 40V, Positive-QTOF	splash10-0059-9400000000-d134c8d5ca17e6bfd5b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 10V, Negative-QTOF	splash10-0006-0900000000-6726d5e015b7a3ce3413	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 20V, Negative-QTOF	splash10-0159-0900000000-69436720531cf9aaf084	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl trans-p-methoxycinnamate 40V, Negative-QTOF	splash10-014i-0900000000-16869d271191168f598d	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002684

KNApSAcK ID

C00034395

Chemspider ID

556588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

641297

PDB ID

Not Available

ChEBI ID

86901

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1432961

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl trans-p-methoxycinnamate (HMDB0030752)

MOL for HMDB0030752 (Methyl trans-p-methoxycinnamate)

3D MOL for HMDB0030752 (Methyl trans-p-methoxycinnamate)

3D SDF for HMDB0030752 (Methyl trans-p-methoxycinnamate)

3D-SDF for HMDB0030752 (Methyl trans-p-methoxycinnamate)

PDB for HMDB0030752 (Methyl trans-p-methoxycinnamate)

3D PDB for HMDB0030752 (Methyl trans-p-methoxycinnamate)

SMILES for HMDB0030752 (Methyl trans-p-methoxycinnamate)

INCHI for HMDB0030752 (Methyl trans-p-methoxycinnamate)

Structure for HMDB0030752 (Methyl trans-p-methoxycinnamate)

3D Structure for HMDB0030752 (Methyl trans-p-methoxycinnamate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra