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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:53:37 UTC

Update Date

2023-02-21 17:25:55 UTC

HMDB ID

HMDB0037644

Secondary Accession Numbers

HMDB37644

Metabolite Identification

Common Name

3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid

Description

3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid has been detected, but not quantified in, common wheats (Triticum aestivum). This could make 3-(2-hydroxy-3-methoxyphenyl)-2-propenoic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid.

Structure

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

  Mrv0541 05061309552D          

 14 14  0  0  0  0            999 V2000
   -0.7145   -1.2375    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
    0.7145   -0.4125    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
    1.4289    2.4750    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    0.0000    0.0000 C   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    0.8250    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
    2.1434    3.7125    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
   -0.7145   -0.4125    0.0000 O   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
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037644

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC(\C=C\C(O)=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-14-8-4-2-3-7(10(8)13)5-6-9(11)12/h2-6,13H,1H3,(H,11,12)/b6-5+

> <INCHI_KEY>
VZFPHVWLPRCAGD-AATRIKPKSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.20788006312282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.6748496726666668

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.85545167127242

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.795890735628311

> <JCHEM_PKA_STRONGEST_BASIC>
-4.893280807747998

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
51.504000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   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   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    3    5   10                                                  
CONECT    8    4   10   14                                                  
CONECT    9    6   11   12                                                  
CONECT   10    7    8   13                                                  
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14    1    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoate	Generator
2-Hydroxy-3-methoxycinnamic acid	HMDB
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid, 9ci	HMDB
O-Ferulic acid	HMDB
Orthoferulic acid	HMDB
(2E)-3-(2-Hydroxy-3-methoxyphenyl)prop-2-enoate	Generator
O-Ferulate	Generator

Chemical Formula

C₁₀H₁₀O₄

Average Molecular Weight

194.184

Monoisotopic Molecular Weight

194.057908808

IUPAC Name

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

Traditional Name

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

CAS Registry Number

3626-94-6

SMILES

COC1=CC=CC(\C=C\C(O)=O)=C1O

InChI Identifier

InChI=1S/C10H10O4/c1-14-8-4-2-3-7(10(8)13)5-6-9(11)12/h2-6,13H,1H3,(H,11,12)/b6-5+

InChI Key

VZFPHVWLPRCAGD-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037644)
Cytoplasm (HMDB: HMDB0037644)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037644)

Source

Exogenous

Exogenous (HMDB: HMDB0037644)

Food

Food (HMDB: HMDB0037644)

Cereal and cereal product

Cereal

Common wheat (FooDB: FOOD00187)

Endogenous

Plant

Plant (HMDB: HMDB0037644)
Poaceae (HMDB: HMDB0037644)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037644)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 - 184 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7191 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	1.08 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.67	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.5 m³·mol⁻¹	ChemAxon
Polarizability	19.21 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
DeepCCS	[M+H]+	144.326	30932474
DeepCCS	[M-H]-	141.723	30932474
DeepCCS	[M-2H]-	177.259	30932474
DeepCCS	[M+Na]+	152.696	30932474
AllCCS	[M+H]+	142.1	32859911
AllCCS	[M+H-H2O]+	137.9	32859911
AllCCS	[M+NH4]+	146.0	32859911
AllCCS	[M+Na]+	147.1	32859911
AllCCS	[M-H]-	140.3	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	141.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid	COC1=CC=CC(\C=C\C(O)=O)=C1O	3404.4	Standard polar	33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid	COC1=CC=CC(\C=C\C(O)=O)=C1O	1816.3	Standard non polar	33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid	COC1=CC=CC(\C=C\C(O)=O)=C1O	1859.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,1TMS,isomer #1	COC1=CC=CC(/C=C/C(=O)O[Si](C)(C)C)=C1O	1988.6	Semi standard non polar	33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,1TMS,isomer #2	COC1=CC=CC(/C=C/C(=O)O)=C1O[Si](C)(C)C	1971.9	Semi standard non polar	33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,2TMS,isomer #1	COC1=CC=CC(/C=C/C(=O)O[Si](C)(C)C)=C1O[Si](C)(C)C	2000.9	Semi standard non polar	33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,1TBDMS,isomer #1	COC1=CC=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=C1O	2238.8	Semi standard non polar	33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,1TBDMS,isomer #2	COC1=CC=CC(/C=C/C(=O)O)=C1O[Si](C)(C)C(C)(C)C	2274.9	Semi standard non polar	33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,2TBDMS,isomer #1	COC1=CC=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2515.0	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 - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-0900000000-e7de9cfa895e19d3fdd3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-7494000000-7d3805761509b289208e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 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 - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 10V, Positive-QTOF	splash10-002b-0900000000-b2737e2bb2b3e29d1c2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 20V, Positive-QTOF	splash10-0002-1900000000-f08a169de3bec4e33b42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 40V, Positive-QTOF	splash10-00vi-9800000000-ef30f17684674bad1995	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 10V, Negative-QTOF	splash10-0006-0900000000-6d81c5b753e9fb152806	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 20V, Negative-QTOF	splash10-0006-0900000000-f7079d7a24d15f4eaabd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 40V, Negative-QTOF	splash10-0564-2900000000-de98d89bab6dc657443f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 10V, Positive-QTOF	splash10-002b-0900000000-97ce251989919a56b869	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 20V, Positive-QTOF	splash10-0002-0900000000-43e9cd0a4c68c7d83c9c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 40V, Positive-QTOF	splash10-01ba-7900000000-aefd94e0ed8c4e65f01f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 10V, Negative-QTOF	splash10-0002-0900000000-2bddd554f2682b7c0b41	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 20V, Negative-QTOF	splash10-001i-0900000000-21fb08b2b2af109ffe26	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 40V, Negative-QTOF	splash10-001i-0900000000-8487a6507ca1e209de5d	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB016760

KNApSAcK ID

Not Available

Chemspider ID

4575887

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5463156

PDB ID

Not Available

ChEBI ID

173938

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1862801

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 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid (HMDB0037644)

MOL for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

3D MOL for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

3D SDF for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

3D-SDF for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

PDB for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

3D PDB for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

SMILES for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

INCHI for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

Structure for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

3D Structure for HMDB0037644 (3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra