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Showing metabocard for 2-Hydroxycinnamic acid (HMDB0002641)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:59 UTC
Update Date2023-02-21 17:16:26 UTC
HMDB IDHMDB0002641
Secondary Accession Numbers
  • HMDB02641
Metabolite Identification
Common Name2-Hydroxycinnamic acid
Description2-coumaric acid, also known as o-coumaric acid, is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 2-coumarate. It is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids: o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. 2-Hydroxycinnamic 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. 2-Hydroxycinnamic acid exists in all living organisms, ranging from bacteria to humans. 2-Hydroxycinnamic acid has been found in a few different foods, such as corns, hard wheats, and olives and in a lower concentration in pomegranates, american cranberries, and peanuts. 2-Hydroxycinnamic acid has also been detected, but not quantified in several different foods, such as carrots, soy beans, ryes, rye bread, and turmerics.
Structure
Data?1676999786
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002641 (2-Hydroxycinnamic acid)


  Mrv1652306141920232D          

 12 12  0  0  0  0            999 V2000
    1.7862    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.8563    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
  9 10  2  0  0  0  0
  2 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0002641 (2-Hydroxycinnamic acid)

HMDB0002641
     RDKit          3D
2-Hydroxycinnamic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.4913    0.6591   -1.8964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3864    0.1673   -0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5029   -0.1531   -0.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191   -0.0559   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653    0.2514   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4205    0.0907   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    0.4939   -1.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    0.3849   -1.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018   -0.1261    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2628   -0.5272    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959   -0.4106    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -0.8253    1.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1539    0.5703    0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -0.4780    0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    0.6827   -1.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225    0.9043   -2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    0.7120   -1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -0.2034    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5726   -0.9361    1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2906   -1.2009    2.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
Download

3D SDF for HMDB0002641 (2-Hydroxycinnamic acid)


  Mrv1652306141920232D          

 12 12  0  0  0  0            999 V2000
    1.7862    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.8563    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
  9 10  2  0  0  0  0
  2 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002641

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+

> <INCHI_KEY>
PMOWTIHVNWZYFI-AATRIKPKSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.158

> <EXACT_MASS>
164.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.10574017590425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.832520938333333

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.352921280175822

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0376342637760265

> <JCHEM_PKA_STRONGEST_BASIC>
-6.04288311541933

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
45.0408

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-coumaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002641 (2-Hydroxycinnamic acid)

HMDB0002641
     RDKit          3D
2-Hydroxycinnamic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.4913    0.6591   -1.8964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3864    0.1673   -0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5029   -0.1531   -0.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191   -0.0559   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653    0.2514   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4205    0.0907   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    0.4939   -1.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    0.3849   -1.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018   -0.1261    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2628   -0.5272    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959   -0.4106    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -0.8253    1.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1539    0.5703    0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -0.4780    0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    0.6827   -1.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225    0.9043   -2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    0.7120   -1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -0.2034    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5726   -0.9361    1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2906   -1.2009    2.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
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PDB for HMDB0002641 (2-Hydroxycinnamic acid)

HEADER    PROTEIN                                 14-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JUN-19         0                                  
HETATM    1  C   UNK     0       3.334   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.000  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.668   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.002   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.336   1.925   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.336   3.465   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.669   1.155   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.000   3.465   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0002641 (2-Hydroxycinnamic acid)

COMPND    HMDB0002641
HETATM    1  O1  UNL     1       3.491   0.659  -1.896  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.386   0.167  -0.750  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.503  -0.153  -0.023  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.019  -0.056  -0.207  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.965   0.251  -0.905  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.420   0.091  -0.507  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.402   0.494  -1.430  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.739   0.385  -1.153  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.202  -0.126   0.044  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.263  -0.527   0.961  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.896  -0.411   0.667  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.018  -0.825   1.617  1.00  0.00           O  
HETATM   13  H1  UNL     1       5.154   0.570   0.259  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.916  -0.478   0.776  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.188   0.683  -1.912  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.122   0.904  -2.389  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.470   0.712  -1.902  1.00  0.00           H  
HETATM   18  H6  UNL     1      -4.263  -0.203   0.242  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.573  -0.936   1.918  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.291  -1.201   2.496  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   11
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   12
CONECT   12   20
END
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SMILES for HMDB0002641 (2-Hydroxycinnamic acid)

OC(=O)\C=C\C1=C(O)C=CC=C1
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INCHI for HMDB0002641 (2-Hydroxycinnamic acid)

InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(2E)-3-(2-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(2-HYDROXYPHENYL)acrylIC ACIDChEBI
(e)-2-Hydroxycinnamic acidChEBI
(e)-3-(2-Hydroxy-phenyl)-acrylic acidChEBI
(e)-3-(2-Hydroxyphenyl)-2-propenoic acidChEBI
(e)-O-Hydroxycinnamic acidChEBI
2-CoumarateChEBI
2-Coumaric acidChEBI
2-HydroxycinnamateChEBI
O-Coumaric acidChEBI
O-Hydroxy-trans-cinnamic acidChEBI
trans-2-HydroxycinnamateChEBI
trans-2-Hydroxycinnamic acidChEBI
trans-O-Hydroxycinnamic acidChEBI
(2E)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(2E)-3-(2-HYDROXYPHENYL)acrylateGenerator
(e)-2-HydroxycinnamateGenerator
(e)-3-(2-Hydroxy-phenyl)-acrylateGenerator
(e)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(e)-O-HydroxycinnamateGenerator
O-CoumarateGenerator
O-Hydroxy-trans-cinnamateGenerator
trans-O-HydroxycinnamateGenerator
2-Hydroxycinnamic acid, (e)-isomerMeSH
Ortho-hydroxycinnamic acidMeSH
2-Hydroxycinnamic acid, (Z)-isomerMeSH
3-(2-Hydroxyphenyl)prop-2-enoateHMDB
3-(2-Hydroxyphenyl)prop-2-enoic acidHMDB
O-HydroxycinnamateHMDB
O-Hydroxycinnamic acidHMDB
ortho-HydroxycinnamateHMDB
trans-O-CoumarateHMDB
trans-O-Coumaric acidHMDB
2-Hydroxycinnamic acidGenerator
trans-2-CoumarateGenerator, HMDB
(E)-3-(2-Hydroxyphenyl)acrylic acidHMDB
3-(2-Hydroxyphenyl)-2-propenoic acidHMDB
o-Hydroxycinnamic acidHMDB
trans-o-Coumaric acidHMDB
3-(2-Hydroxyphenyl)acrylic acidHMDB
trans-2-Coumaric acid HMDB
(2E)-3-(2-Hydroxyphenyl)prop-2-enoic acidHMDB
2'-Hydroxycinnamic acidHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid
Traditional NameO-coumaric acid
CAS Registry Number614-60-8
SMILES
OC(=O)\C=C\C1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+
InChI KeyPMOWTIHVNWZYFI-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point348.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility27090 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.430 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available127.336http://allccs.zhulab.cn/database/detail?ID=AllCCS00000435
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+134.20930932474
DeepCCS[M-H]-131.71330932474
DeepCCS[M-2H]-167.36330932474
DeepCCS[M+Na]+142.10430932474
AllCCS[M+H]+134.632859911
AllCCS[M+H-H2O]+130.232859911
AllCCS[M+NH4]+138.732859911
AllCCS[M+Na]+139.932859911
AllCCS[M-H]-131.632859911
AllCCS[M+Na-2H]-132.532859911
AllCCS[M+HCOO]-133.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.8 minutes32390414
Predicted by Siyang on May 30, 202210.3462 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.65 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1479.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid332.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid122.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid198.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid129.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid398.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid357.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)117.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid883.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid331.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid981.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid220.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid312.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate469.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA234.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water90.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxycinnamic acidOC(=O)\C=C\C1=C(O)C=CC=C13074.6Standard polar33892256
2-Hydroxycinnamic acidOC(=O)\C=C\C1=C(O)C=CC=C11557.1Standard non polar33892256
2-Hydroxycinnamic acidOC(=O)\C=C\C1=C(O)C=CC=C11626.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxycinnamic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O1834.0Semi standard non polar33892256
2-Hydroxycinnamic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC=C1/C=C/C(=O)O1787.8Semi standard non polar33892256
2-Hydroxycinnamic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[Si](C)(C)C1833.2Semi standard non polar33892256
2-Hydroxycinnamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O2068.0Semi standard non polar33892256
2-Hydroxycinnamic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC=C1/C=C/C(=O)O2077.8Semi standard non polar33892256
2-Hydroxycinnamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[Si](C)(C)C(C)(C)C2300.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0910000000-9e0bdbf6d6389288e3182014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9710000000-829ded288e3ec83121602014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9710000000-8fb7bb39d916f74029802014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-MS (2 TMS)splash10-0296-2941000000-b85ebef8eb8c276f220f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid EI-B (Non-derivatized)splash10-014i-9800000000-3650ee76a1293cba75232017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-9e0bdbf6d6389288e3182017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-EI-TOF (Non-derivatized)splash10-00dj-9710000000-829ded288e3ec83121602017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-EI-TOF (Non-derivatized)splash10-00dj-9710000000-8fb7bb39d916f74029802017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-MS (Non-derivatized)splash10-0296-2941000000-b85ebef8eb8c276f220f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Hydroxycinnamic acid GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-c783499d6f33717b71ca2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-3a06c14b7e8999427ad92017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxycinnamic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-a82ff5bd6498e3c478ea2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxycinnamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014j-8900000000-8e96a9ec1b9d035d3edb2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-03di-0900000000-9e4823d321cfe6f5e5a42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-014i-0900000000-efd5de4e7fe4032816f62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-014i-0900000000-44e81c2c735a93efc7d72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-014l-7900000000-977a2bb08508d16be5312012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0fdn-4900000000-dcfe2b032cf6bbee16b32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-03di-0900000000-adbaf7b04487b18191e02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ , negative-QTOFsplash10-03di-0900000000-d368e3c354c7b05a949f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-efd5de4e7fe4032816f62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-44e81c2c735a93efc7d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ , negative-QTOFsplash10-014l-7900000000-a641b2c2528f829e8ac12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QQ , negative-QTOFsplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QTOF , negative-QTOFsplash10-03di-0900000000-adbaf7b04487b18191e02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid Linear Ion Trap , negative-QTOFsplash10-014i-0900000000-2ca69c9285dedaa2f4242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid Linear Ion Trap , negative-QTOFsplash10-014i-0900000000-55078e8ec591840fb5942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid LC-ESI-QTOF , positive-QTOFsplash10-0fdn-4900000000-95f5386456c1c353a1112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxycinnamic acid 35V, Negative-QTOFsplash10-014i-0900000000-bf00664334bbd7d7d91d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycinnamic acid 10V, Positive-QTOFsplash10-014j-0900000000-ba0915b2f87da989c92b2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycinnamic acid 20V, Positive-QTOFsplash10-014i-2900000000-fd2da9ac5865a50fc50c2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycinnamic acid 40V, Positive-QTOFsplash10-0gdu-9300000000-3baee6b4124fba79677e2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycinnamic acid 10V, Negative-QTOFsplash10-03di-0900000000-69f05779283af436427d2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycinnamic acid 20V, Negative-QTOFsplash10-03xr-1900000000-0bc76f24c2abf6670fc02017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycinnamic acid 40V, Negative-QTOFsplash10-0006-9600000000-a2981a5342a71b94ce692017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycinnamic acid 10V, Negative-QTOFsplash10-014i-0900000000-972f865a96261dcb891a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxycinnamic acid 20V, Negative-QTOFsplash10-014j-0900000000-dfdb5072d39445a67f3a2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.904 +/- 0.337 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.188 +/- 0.059 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.339 +/- 0.088 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.366 +/- 0.164 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.521 +/- 0.278 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.58 +/- 0.184 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified3.528 +/- 3.295 uMAdult (>18 years old)Male
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.213 +/- 0.099 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01650
Phenol Explorer Compound ID462
FooDB IDFDB011258
KNApSAcK IDC00002729
Chemspider ID553146
KEGG Compound IDC01772
BioCyc ID2-COUMARATE
BiGG IDNot Available
Wikipedia LinkO-Coumaric_acid
METLIN ID6727
PubChem Compound637540
PDB IDNot Available
ChEBI ID18125
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1176751
References
Synthesis ReferenceAdams, Roger; Bockstahler, Theodore E. Preparation and reactions of o-hydroxycinnamic acids and esters. Journal of the American Chemical Society (1952), 74 5346-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]