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Showing metabocard for trans-Cinnamic acid (HMDB0000930)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:18 UTC
HMDB IDHMDB0000930
Secondary Accession Numbers
  • HMDB00930
Metabolite Identification
Common Nametrans-Cinnamic acid
Descriptiontrans-Cinnamic acid, also known as (e)-cinnamic acid or phenylacrylic acid, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. trans-Cinnamic acid exists in all living species, ranging from bacteria to humans. trans-Cinnamic acid is a sweet, balsam, and cinnamon tasting compound. Outside of the human body, trans-Cinnamic acid is found, on average, in the highest concentration within a few different foods, such as chinese cinnamons, olives, and lingonberries and in a lower concentration in redcurrants, red raspberries, and corianders. trans-Cinnamic acid has also been detected, but not quantified in several different foods, such as common oregano, pepper (spice), fennels, pomegranates, and european cranberries. This could make trans-cinnamic acid a potential biomarker for the consumption of these foods. Cinnamic acid has been shown to be a microbial metabolite; it can be found in Alcaligenes, Brevibacterium, Cellulomonas, and Pseudomonas (PMID:16349793 ). trans-Cinnamic acid is a potentially toxic compound.
Structure
Data?1676999718
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000930 (trans-Cinnamic acid)


  Mrv1652309272007382D          

 11 11  0  0  0  0            999 V2000
   -0.8703    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    0.4124    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
  6  1  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 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000930 (trans-Cinnamic acid)

HMDB0000930
     RDKit          3D
trans-Cinnamic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    4.3195   -1.0333    0.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -0.2120   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206    0.9754   -0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091   -0.5317    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    0.3242   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3506    0.1041    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977   -1.0648    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -1.2113    0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.2449    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247    0.9256   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.0695   -0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    1.8639   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -1.4660    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.2833   -0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.8739    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935   -2.1519    1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -0.4403    0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3136    1.6979   -0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8626    1.9862   -0.7971 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  6  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for HMDB0000930 (trans-Cinnamic acid)


  Mrv1652309272007382D          

 11 11  0  0  0  0            999 V2000
   -0.8703    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    0.4124    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
  6  1  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 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000930

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+

> <INCHI_KEY>
WBYWAXJHAXSJNI-VOTSOKGWSA-N

> <FORMULA>
C9H8O2

> <MOLECULAR_WEIGHT>
148.1586

> <EXACT_MASS>
148.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.428464888087186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-phenylprop-2-enoic acid

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.13608626

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.509231934706283

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
43.0599

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinnamic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000930 (trans-Cinnamic acid)

HMDB0000930
     RDKit          3D
trans-Cinnamic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    4.3195   -1.0333    0.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -0.2120   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206    0.9754   -0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091   -0.5317    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    0.3242   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3506    0.1041    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977   -1.0648    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -1.2113    0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.2449    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247    0.9256   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.0695   -0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    1.8639   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -1.4660    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.2833   -0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.8739    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935   -2.1519    1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -0.4403    0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3136    1.6979   -0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8626    1.9862   -0.7971 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  6  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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PDB for HMDB0000930 (trans-Cinnamic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.625   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.958   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.292   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.292  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.958  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.625  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.291   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.043   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.376   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.376   3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.710   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
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   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0000930 (trans-Cinnamic acid)

COMPND    HMDB0000930
HETATM    1  O1  UNL     1       4.319  -1.033   0.202  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.429  -0.212  -0.111  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.821   0.975  -0.694  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.009  -0.532   0.149  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.068   0.324  -0.175  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.351   0.104   0.039  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.798  -1.065   0.617  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.161  -1.211   0.793  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.062  -0.245   0.414  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.625   0.926  -0.165  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.270   1.070  -0.339  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.409   1.864  -0.540  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.749  -1.466   0.605  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.370   1.283  -0.645  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.116  -1.874   0.941  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.494  -2.152   1.256  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.122  -0.440   0.588  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.314   1.698  -0.471  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.863   1.986  -0.797  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   13
CONECT    5    6   14
CONECT    6    7    7   11
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   10   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for HMDB0000930 (trans-Cinnamic acid)

OC(=O)\C=C\C1=CC=CC=C1
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INCHI for HMDB0000930 (trans-Cinnamic acid)

InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(2E)-3-Phenyl-2-propenoic acidChEBI
(2E)-3-Phenylacrylic acidChEBI
(e)-3-Phenyl-2-propenoic acidChEBI
(e)-CinnamateChEBI
(e)-Cinnamic acidChEBI
Benzeneacrylic acidChEBI
PHENYLETHYLENECARBOXYLIC ACIDChEBI
trans-3-Phenylacrylic acidChEBI
trans-beta-CarboxystyreneChEBI
trans-CinnamateChEBI
trans-ZimtsaeureChEBI
(2E)-3-Phenyl-2-propenoateGenerator
(2E)-3-PhenylacrylateGenerator
(e)-3-Phenyl-2-propenoateGenerator
BenzeneacrylateGenerator
PHENYLETHYLENECARBOXYLateGenerator
trans-3-PhenylacrylateGenerator
trans-b-CarboxystyreneGenerator
trans-Β-carboxystyreneGenerator
(2E)-2-Phenyl-2-propenoateHMDB
(2E)-2-Phenyl-2-propenoic acidHMDB
(e)-3-PhenylacrylateHMDB
(e)-3-Phenylacrylic acidHMDB
(e)-3-Phenylprop-2-enoateHMDB
(e)-3-Phenylprop-2-enoic acidHMDB
trans-3-Phenyl-2-propenoateHMDB
trans-3-Phenyl-2-propenoic acidHMDB
Cinnamic acid, 14C-labeled CPDHMDB
Cinnamic acid, 2-(14)C-labeled CPDHMDB
Cinnamic acid, 3-(14)C-labeled CPDHMDB
Cinnamic acid, (Z)-isomerHMDB
Cinnamic acid, 2-(13)C-labeled CPDHMDB
Cinnamic acid, 3H-labeled CPD (e)-isomerHMDB
Cinnamic acid, 3H-labeled CPD (Z)-isomerHMDB
Cinnamic acid, ion(1-)-(e)-isomerHMDB
Cinnamic acid, sodium saltHMDB
Cinnamic acid, sodium salt(e)-isomerHMDB
Cinnamic acid, sodium salt(Z)-isomerHMDB
Cinnamic acid, (trans)-(e)-isomerHMDB
Cinnamic acid, 14C-labeled CPD (e)-isomerHMDB
Cinnamic acid, ion(1-)HMDB
Cinnamic acid, nickel (+2) saltHMDB
Cinnamic acid, potassium saltHMDB
Cinnamic acid, zinc salt(e)-isomerHMDB
Cinnamic acid, 13C-labeled CPDHMDB
Cinnamic acidHMDB
(2E)-3-Phenylprop-2-enoic acidHMDB
(2E)-Cinnamic acidHMDB
3-Phenyl-(e)-2-propenoic acidHMDB
3-Phenyl-2-propenoic acidHMDB
3-Phenylacrylic acidHMDB
Phenylacrylic acidHMDB
beta-Phenylacrylic acidHMDB
Β-phenylacrylic acidHMDB
trans-Cinnamic acidHMDB
Chemical FormulaC9H8O2
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
IUPAC Name(2E)-3-phenylprop-2-enoic acid
Traditional Namecinnamic acid
CAS Registry Number140-10-3
SMILES
OC(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
InChI KeyWBYWAXJHAXSJNI-VOTSOKGWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point133 °CNot Available
Boiling Point298.00 to 300.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.55 mg/mLNot Available
LogP2.13HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available135.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000542
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.74131661259
DarkChem[M-H]-129.42831661259
AllCCS[M+H]+130.48132859911
AllCCS[M-H]-128.56532859911
DeepCCS[M+H]+129.40730932474
DeepCCS[M-H]-126.60630932474
DeepCCS[M-2H]-162.72430932474
DeepCCS[M+Na]+137.96830932474
AllCCS[M+H]+130.532859911
AllCCS[M+H-H2O]+126.032859911
AllCCS[M+NH4]+134.732859911
AllCCS[M+Na]+135.932859911
AllCCS[M-H]-128.632859911
AllCCS[M+Na-2H]-129.832859911
AllCCS[M+HCOO]-131.132859911

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, 2022.5.24 minutes32390414
Predicted by Siyang on May 30, 202212.449 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.54 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1951.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid415.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid152.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid267.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid221.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid472.4 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 Acid496.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)127.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1103.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid418.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1139.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid286.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid379.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate445.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA317.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water57.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-Cinnamic acidOC(=O)\C=C\C1=CC=CC=C12773.6Standard polar33892256
trans-Cinnamic acidOC(=O)\C=C\C1=CC=CC=C11370.5Standard non polar33892256
trans-Cinnamic acidOC(=O)\C=C\C1=CC=CC=C11442.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-Cinnamic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C11551.3Semi standard non polar33892256
trans-Cinnamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C11791.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0ue9-0910000000-4a7bcdfadd383bf577dc2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0fb9-6920000000-727a2eb761e6e52fb47d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-MS (1 TMS)splash10-117i-2920000000-f0d9ccc40786362ae4ad2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-EI-TOF (Non-derivatized)splash10-0ue9-0910000000-4a7bcdfadd383bf577dc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-EI-TOF (Non-derivatized)splash10-0fb9-6920000000-727a2eb761e6e52fb47d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-MS (Non-derivatized)splash10-117i-2920000000-f0d9ccc40786362ae4ad2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Cinnamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-2900000000-b105b3fcb63636d0d16f2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Cinnamic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Cinnamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Cinnamic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f6t-6900000000-77686ecc684f3b46bea62014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0900000000-3107a2a1bec368528f822012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0ufr-6900000000-b0299d34fa9bb16b82582012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0udi-0900000000-4a879de8ea4f3acb0ae22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0002-0900000000-88ad8c9c837a057bb2a52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0udi-0900000000-18280fe18e43043d9e212012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0fb9-9600000000-04d36ba7639bc85e20232012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-9000000000-a8417274c4493c5b58712012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-9100000000-d3712417826a696679812012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-0900000000-37c486fa03918355413c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0f6t-0900000000-218a5babf0ab7c31c4982012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-0002-0900000000-88ad8c9c837a057bb2a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-0udi-0900000000-e3a4fcaa911f14d3790d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-0fb9-9600000000-04d36ba7639bc85e20232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-a8417274c4493c5b58712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9100000000-d3712417826a696679812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QTOF , negative-QTOFsplash10-0f6t-0900000000-218a5babf0ab7c31c4982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Linear Ion Trap , negative-QTOFsplash10-0udi-0900000000-f095c04fe81b2890cb1a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Linear Ion Trap , negative-QTOFsplash10-0udi-0900000000-1bb9599f57d5b1c1688b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-37c486fa03918355413c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 10V, Positive-QTOFsplash10-000t-0900000000-f5b771d960092fa83d2c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 20V, Positive-QTOFsplash10-0uea-0900000000-58b4769b89ab3883fb052016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 40V, Positive-QTOFsplash10-0udi-6900000000-9f4710d90f0cafac6d7b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 10V, Negative-QTOFsplash10-0002-0900000000-d015607beb51363244142016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 20V, Negative-QTOFsplash10-0f6t-0900000000-ff32add65ca52cbaae832016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 40V, Negative-QTOFsplash10-0fb9-3900000000-f2450299b70c3ec0faec2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX 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+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 Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.869 +/- 1.14 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 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 IDNot Available
Phenol Explorer Compound ID549
FooDB IDFDB012052
KNApSAcK IDC00000170
Chemspider ID392447
KEGG Compound IDC10438
BioCyc IDCPD-674
BiGG IDNot Available
Wikipedia LinkCinnamic_acid
METLIN ID5880
PubChem Compound444539
PDB IDNot Available
ChEBI ID35697
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1350711
References
Synthesis ReferenceZhu, Min; Shentu, Chao; Zhou, Zhong Shi. Microwave-assisted base-free synthesis of trans-cinnamic acids using hypervalent iodonium salts. Chinese Chemical Letters (2007), 18(3), 272-274.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
  2. Blanquet S, Meunier JP, Minekus M, Marol-Bonnin S, Alric M: Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment. Appl Environ Microbiol. 2003 May;69(5):2884-92. [PubMed:12732562 ]
  3. Sarkissian CN, Shao Z, Blain F, Peevers R, Su H, Heft R, Chang TM, Scriver CR: A different approach to treatment of phenylketonuria: phenylalanine degradation with recombinant phenylalanine ammonia lyase. Proc Natl Acad Sci U S A. 1999 Mar 2;96(5):2339-44. [PubMed:10051643 ]
  4. Wahl HG, Hong Q, Stube D, Maier ME, Haring HU, Liebich HM: Simultaneous analysis of the di(2-ethylhexyl)phthalate metabolites 2-ethylhexanoic acid, 2-ethyl-3-hydroxyhexanoic acid and 2-ethyl-3-oxohexanoic acid in urine by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):213-9. [PubMed:11486831 ]
  5. Larue C, Munnich A, Charpentier C, Saudubray JM, Frezal J, Remy MH, Rivat C: An extracorporeal hollow-fiber reactor for phenylketonuria using immobilized phenylalanine ammonia lyase. Dev Pharmacol Ther. 1986;9(2):73-81. [PubMed:3956347 ]
  6. Olivera ER, Carnicero D, Jodra R, Minambres B, Garcia B, Abraham GA, Gallardo A, Roman JS, Garcia JL, Naharro G, Luengo JM: Genetically engineered Pseudomonas: a factory of new bioplastics with broad applications. Environ Microbiol. 2001 Oct;3(10):612-8. [PubMed:11722541 ]
  7. Lee HS, Beon MS, Kim MK: Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. J Agric Food Chem. 2001 Oct;49(10):4656-61. [PubMed:11600003 ]
  8. Douros JD, Frankenfeld JW: Effects of Culture Conditions on Production of trans-Cinnamic Acid from Alkylbenzenes by Soil Microorganisms. Appl Microbiol. 1968 Feb;16(2):320-5. [PubMed:16349793 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
trans-Cinnamic acid → 3,4,5-trihydroxy-6-{[(2E)-3-phenylprop-2-enoyl]oxy}oxane-2-carboxylic aciddetails