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Showing NP-Card for trans-Cinnamic acid (NP0001281)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-04-19 10:06:04 UTC
NP-MRD IDNP0001281
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001281 (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 NP0001281 (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 NP0001281 (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>
NP0001281

> <DATABASE_NAME>
NP-MRD

> <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 NP0001281 (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 NP0001281 (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 NP0001281 (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 NP0001281 (trans-Cinnamic acid)

OC(=O)\C=C\C1=CC=CC=C1
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INCHI for NP0001281 (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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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
(e)-Cinnamic acid, 2-(14)C-labeled CPDMeSH
e-Z Cinnamic acidMeSH
cis-Cinnamic acidMeSH
Sodium cinnamateMeSH
Cinnamic acid, radical ion(1-)MeSH
e-Cinnamic acidMeSH
Cinnamic acid, 1-14C-labeled CPDMeSH
Cinnamic acid, 1-(13)C-labeled CPDMeSH
Tritium labeled (e)-cinnamic acidMeSH
Tritium labeled (Z)-cinnamic acidMeSH
Chemical FormulaC9H8O2
Average Mass148.1586 Da
Monoisotopic Mass148.05243 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-14View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-14View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201.216488466 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Adenostoma sparsifoliumLOTUS Database
Aegle marmelosLOTUS Database
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
AgaveFooDB
Aiouea brenesiiLOTUS Database
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloe castellorumLOTUS Database
Aloysia triphyllaFooDB
Alpinia formosanaLOTUS Database
Alpinia galangaLOTUS Database
Alpinia spp.KNApSAcK Database
Alpinia tonkinensisLOTUS Database
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Anadenanthera colubrinaLOTUS Database
Ananas comosusFooDB
Anas platyrhynchosFooDB
Anastatica hierochunticaLOTUS Database
AnatidaeFooDB
Andrographis paniculataLOTUS Database
Andryala pinnatifidaLOTUS Database
Anethum graveolensFooDB
Angelica keiskeiFooDB
Anigozanthos preissiiLOTUS Database
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Aragoa lucidulaLOTUS Database
Arctium lappaFooDB
Aristolochia elegansLOTUS Database
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia judaicaLOTUS Database
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Balanophora fungosaLOTUS Database
Balanophora tobiracolaLOTUS Database
Balsamorhiza sagittataLOTUS Database
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Betula pendulaLOTUS Database
Betula pubescensLOTUS Database
Bison bisonFooDB
Bletilla striataLOTUS Database
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusKNApSAcK Database
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesKNApSAcK Database
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bryothamnion triquetrumLOTUS Database
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Camellia sinensisLOTUS Database
Cananga odorataLOTUS Database
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catharanthus roseusKNApSAcK Database
Ceanothus velutinusLOTUS Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Cheniella glaucaLOTUS Database
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum spp.KNApSAcK Database
Cinnamomum verumFooDB
CirsiumFooDB
Cistus ladaniferusKNApSAcK Database
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiKNApSAcK Database
Citrus reticulataFooDB
Citrus sinensisLOTUS Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia antiquorumLOTUS Database
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Conocephalum conicumLOTUS Database
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Corymbia maculataLOTUS Database
Crateva religiosaFooDB
Crocus sativusFooDB
Cryptocarya amygdalinaLOTUS Database
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativusLOTUS Database
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daphnia pulexLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dicksonia karstenianaLOTUS Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea alataKNApSAcK Database
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Duranta erectaLOTUS Database
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Engelhardia roxburghianaLOTUS Database
Ephedra distachyaLOTUS Database
Ephedra equisetinaLOTUS Database
Ephedra sinicaKNApSAcK Database
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Erythroxylum cocaKNApSAcK Database
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Euphorbia micractinaLOTUS Database
Euphorbia tithymaloidesLOTUS Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria moschataLOTUS Database
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaultheria borneensisLOTUS Database
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Globularia alypumLOTUS Database
Globularia spp.KNApSAcK Database
Glycine maxKNApSAcK Database
Goniothalamus amuyonLOTUS Database
Goniothalamus tenuifoliusLOTUS Database
GossypiumFooDB
Goupia glabraLOTUS Database
Grifola frondosaFooDB
Gymnophyton isatidicarpumLOTUS Database
Gynerium sagittatumKNApSAcK Database
Haplopappus foliosusLOTUS Database
Harpagophytum procumbensLOTUS Database
Harpagophytum zeyheriLOTUS Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusKNApSAcK Database
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hoya cinnamomifoliaLOTUS Database
Hyssopus officinalis L.FooDB
Illicium fargesiiLOTUS Database
Illicium verumFooDB
Inula grandisLOTUS Database
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
Ipomoea leptophyllaLOTUS Database
Isodon japonicusLOTUS Database
Isotachis japonicaLOTUS Database
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Kaempferia galangaLOTUS Database
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lagotis yunnanensisLOTUS Database
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Leucophyllum ambiguumKNApSAcK Database
Levisticum officinaleFooDB
Lilium candidumKNApSAcK Database
Lindsaea javanensisLOTUS Database
Linum usitatissimumFooDB
Liquidambar orientalisKNApSAcK Database
Litchi chinensisFooDB
Lonicera japonicaLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lychnophora ericoidesLOTUS Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Magnolia denudataKNApSAcK Database
Magnolia liliifloraKNApSAcK Database
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mandragora officinarumLOTUS Database
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Marsypopetalum crassumLOTUS Database
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melia azedarachLOTUS Database
Melissa officinalisKNApSAcK Database
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilodaphne quixosLOTUS Database
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus bombycisLOTUS Database
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum americanumLOTUS Database
Ocimum basilicumKNApSAcK Database
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Onychium lucidumLOTUS Database
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Oxalis pes-capraeLOTUS Database
Ozothamnus diosmifoliusLOTUS Database
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Parthenium argentatumKNApSAcK Database
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Pelargonium incrassatumLOTUS Database
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Petunia axillarisLOTUS Database
Phaseolus aureusKNApSAcK Database
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phellodendron amurenseLOTUS Database
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllanthus emblicaLOTUS Database
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimenta racemosaLOTUS Database
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Pinus lambertianaLOTUS Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumKNApSAcK Database
Plantago lanceolataLOTUS Database
Plantago majorLOTUS Database
Platostoma africanumLOTUS Database
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Plinia caulifloraLOTUS Database
Polygonum alpinumFooDB
Polygonum minusKNApSAcK Database
Populus balsamiferaLOTUS Database
Populus deltoidesLOTUS Database
Populus nigraLOTUS Database
Populus spp.KNApSAcK Database
Populus trichocarpaLOTUS Database
Portulaca oleraceaFooDB
Posidonia oceanicaLOTUS Database
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Rhodiola roseaLOTUS Database
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Sauromatum giganteumLOTUS Database
Schisandra chinensisLOTUS Database
Scorzonera hispanicaFooDB
Scrophularia buergerianaLOTUS Database
Scrophularia ningpoensisLOTUS Database
Scrophularia nodosaKNApSAcK Database
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sophora flavescensKNApSAcK Database
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Sphagneticola trilobataLOTUS Database
Spinacia oleraceaFooDB
Spiraea salicifoliaLOTUS Database
Spiraea thunbergiiLOTUS Database
Streptomyces maritimusLOTUS Database
Strobilanthes yunnanensisLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syringa persicaLOTUS Database
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tarenna attenuataLOTUS Database
Taxus baccataLOTUS Database
Tetragonia tetragonioidesFooDB
Tetrapanax papyriferLOTUS Database
Tetrapanax papyriferusKNApSAcK Database
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Viscum coloratumLOTUS Database
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis rupestrisKNApSAcK Database
Vitis viniferaKNApSAcK Database
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zanthoxylum armatumLOTUS Database
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Pleurocybella porrigensKNApSAcK Database
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
Physical Properties
StateSolid
Experimental 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted 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
HMDB IDHMDB0000930
DrugBank IDNot Available
Phenol Explorer Compound ID549
FoodDB IDFDB031209
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
Good Scents IDrw1350711
References
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. doi: 10.1128/am.16.2.320-325.1968. [PubMed:16349793 ]