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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:21:34 UTC

Update Date

2021-09-23 18:21:34 UTC

HMDB ID

HMDB0302514

Secondary Accession Numbers

None

Metabolite Identification

Common Name

trans-2-Methoxycinnamic acid

Description

Trans-2-methoxycinnamic acid is a member of the class of compounds known as coumaric acids. Coumaric acids are aromatic compounds containing a cinnamic acid moiety hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Trans-2-methoxycinnamic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Trans-2-methoxycinnamic acid can be found in chinese cinnamon, which makes trans-2-methoxycinnamic acid a potential biomarker for the consumption of this food product.

Structure

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

  Mrv0541 09041212492D          

 15 15  0  0  0  0            999 V2000
    1.4289    2.4750    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
    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
    1.4289    0.8250    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    2.0625    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    1.2375    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
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
   -1.4289    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  2  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302514

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(\[H])C1=CC=CC=C1OC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-13-9-5-3-2-4-8(9)6-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-6+

> <INCHI_KEY>
FEGVSPGUHMGGBO-VOTSOKGWSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.22241402068024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(2-methoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
1.978414994333333

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.142687254409233

> <JCHEM_PKA_STRONGEST_BASIC>
-4.841551348441892

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
49.523100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(2-methoxyphenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   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       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    7    8   14                                                  
CONECT    7    6   10   15                                                  
CONECT    8    4    6    9                                                  
CONECT    9    5    8   13                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1    9                                                       
CONECT   14    6                                                            
CONECT   15    7                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-3-(2-Methoxyphenyl)-2-propenoic acid	ChEBI
(e)-3-(2-Methoxyphenyl)acrylic acid	ChEBI
(e)-O-Methoxycinnamic acid	ChEBI
2-Methoxycinnamic acid	ChEBI
trans-2-Methoxycinnamic acid	ChEBI
(e)-3-(2-Methoxyphenyl)-2-propenoate	Generator
(e)-3-(2-Methoxyphenyl)acrylate	Generator
(e)-O-Methoxycinnamate	Generator
2-Methoxycinnamate	Generator
trans-2-Methoxycinnamate	Generator
(e)-2-Methoxycinnamate	Generator

Chemical Formula

C₁₀H₁₀O₃

Average Molecular Weight

178.1846

Monoisotopic Molecular Weight

178.062994186

IUPAC Name

(2E)-3-(2-methoxyphenyl)prop-2-enoic acid

Traditional Name

(2E)-3-(2-methoxyphenyl)prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=CC=C1OC)C(O)=O

InChI Identifier

InChI=1S/C10H10O3/c1-13-9-5-3-2-4-8(9)6-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-6+

InChI Key

FEGVSPGUHMGGBO-VOTSOKGWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids. These are aromatic compounds containing a cinnamic acid moiety 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

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302514)

Food

Herb and spice

Spice

Chinese cinnamon (FooDB: FOOD00050)

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	2.38	ALOGPS
logP	1.98	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.52 m³·mol⁻¹	ChemAxon
Polarizability	18.22 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]+	138.095	32859911
AllCCS	[M+H-H2O]+	133.786	32859911
AllCCS	[M+Na]+	143.267	32859911
AllCCS	[M+NH4]+	142.109	32859911
AllCCS	[M-H]-	136.436	32859911
AllCCS	[M+Na-2H]-	137.208	32859911
AllCCS	[M+HCOO]-	138.135	32859911
DeepCCS	[M+H]+	136.224	30932474
DeepCCS	[M-H]-	133.828	30932474
DeepCCS	[M-2H]-	167.08	30932474
DeepCCS	[M+Na]+	142.136	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - trans-2-Methoxycinnamic acid GC-MS (1 TMS)	splash10-02vi-3940000000-08e47fe2d1ef428337fe	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - trans-2-Methoxycinnamic acid GC-MS (1 TMS)	splash10-0gyc-3920000000-6a8a02b6b2e7c8b4cb32	2014-06-16	HMDB team, MONA, MassBank	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 10V, Negative-QTOF	splash10-004i-0900000000-97d4050612e3d3614c55	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 20V, Negative-QTOF	splash10-004i-0900000000-b8e3ccb90a2adb2986a7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 40V, Negative-QTOF	splash10-05nf-5900000000-fed71ccb81b86eb9d7a8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 10V, Negative-QTOF	splash10-0arr-0900000000-303ae88751ee0cc820ea	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 20V, Negative-QTOF	splash10-0gb9-0900000000-c6a353de42455f9e358c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 40V, Negative-QTOF	splash10-014i-0900000000-59d189614ecf1a727514	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 10V, Positive-QTOF	splash10-01t9-0900000000-6b7bbdcd75ddbbe30e62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 20V, Positive-QTOF	splash10-01si-1900000000-7a017f4610241ad78787	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 40V, Positive-QTOF	splash10-0ufr-6900000000-3d4d0e914dc88af855ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 10V, Positive-QTOF	splash10-0059-0900000000-d80b6ee7ed76b990f260	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 20V, Positive-QTOF	splash10-001i-2900000000-ba27a3f739f2a1c7daa9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Methoxycinnamic acid 40V, Positive-QTOF	splash10-002r-9300000000-b067241e9b4b82dd8fc1	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

FDB004884

KNApSAcK ID

Not Available

Chemspider ID

641429

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

734154

PDB ID

Not Available

ChEBI ID

136676

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1417171

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for trans-2-Methoxycinnamic acid (HMDB0302514)

MOL for HMDB0302514 (trans-2-Methoxycinnamic acid)

3D MOL for HMDB0302514 (trans-2-Methoxycinnamic acid)

3D SDF for HMDB0302514 (trans-2-Methoxycinnamic acid)

3D-SDF for HMDB0302514 (trans-2-Methoxycinnamic acid)

PDB for HMDB0302514 (trans-2-Methoxycinnamic acid)

3D PDB for HMDB0302514 (trans-2-Methoxycinnamic acid)

SMILES for HMDB0302514 (trans-2-Methoxycinnamic acid)

INCHI for HMDB0302514 (trans-2-Methoxycinnamic acid)

Structure for HMDB0302514 (trans-2-Methoxycinnamic acid)

3D Structure for HMDB0302514 (trans-2-Methoxycinnamic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra