Np mrd loader

Showing NP-Card for Cinnamic acid (NP0000419)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:44 UTC
NP-MRD IDNP0000419
Secondary Accession NumbersNone
Natural Product Identification
Common NameCinnamic acid
DescriptionCinnamic acid, also known as (Z)-cinnamate or 3-phenyl-acrylate, 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. Cinnamic acid can be obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Cinnamic acid exists in all living organisms, ranging from bacteria to plants to humans. Outside of the human body, cinnamic acid has been detected, but not quantified in, chinese cinnamons. In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000419 (Cinnamic acid)


  Mrv1652306201922002D          

 11 11  0  0  0  0            999 V2000
10000.291310000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.116310000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.832010000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.545610000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.8320 9999.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.577710000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.863310000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.148710000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1487 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8632 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5777 9999.5878    0.0000 C   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  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
  1  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000419 (Cinnamic acid)

HMDB0000567
     RDKit          3D
Cinnamic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.0012    0.1928    0.3864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952    0.1611    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056    1.0343    1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2202   -0.8048   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -1.0097   -1.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853   -0.3238   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447    0.9871   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5576    1.4621    0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6482    0.6526    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983   -0.6723    0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -1.1489   -0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.0367    2.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0257   -1.4629   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721   -1.8643   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4352    1.7250   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327    2.5071    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5817    1.0226    0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -1.3064    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2521   -2.1884   -0.6054 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 NP0000419 (Cinnamic acid)


  Mrv1652306201922002D          

 11 11  0  0  0  0            999 V2000
10000.291310000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.116310000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.832010000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.545610000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.8320 9999.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.577710000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.863310000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.148710000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1487 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8632 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5777 9999.5878    0.0000 C   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  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
  1  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000419

> <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-SREVYHEPSA-N

> <FORMULA>
C9H8O2

> <MOLECULAR_WEIGHT>
148.1586

> <EXACT_MASS>
148.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.026333545368203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-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>
4.009231934706283

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
43.059900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-cinnamic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000419 (Cinnamic acid)

HMDB0000567
     RDKit          3D
Cinnamic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.0012    0.1928    0.3864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952    0.1611    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056    1.0343    1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2202   -0.8048   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9972   -1.0097   -1.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853   -0.3238   -0.5853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447    0.9871   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5576    1.4621    0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6482    0.6526    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983   -0.6723    0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -1.1489   -0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.0367    2.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0257   -1.4629   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721   -1.8643   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4352    1.7250   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327    2.5071    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5817    1.0226    0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -1.3064    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2521   -2.1884   -0.6054 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

PDB for NP0000419 (Cinnamic acid)

HEADER    PROTEIN                                 20-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-19         0                                  
HETATM    1  C   UNK     0    8667.2108668.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.7508668.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.0868667.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8671.4188668.207   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8670.0868665.899   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8665.8788667.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.5458668.207   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.2118667.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.2118665.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.5458665.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.8788665.897   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   11    1                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
Download

3D PDB for NP0000419 (Cinnamic acid)

COMPND    HMDB0000567
HETATM    1  O1  UNL     1      -4.001   0.193   0.386  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.695   0.161   0.271  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.006   1.034   1.046  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.220  -0.805  -0.652  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.997  -1.010  -1.003  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.185  -0.324  -0.585  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.345   0.987  -0.263  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.558   1.462   0.254  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.648   0.653   0.464  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.498  -0.672   0.138  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.324  -1.149  -0.365  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.143   1.037   2.040  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.026  -1.463  -1.124  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.872  -1.864  -1.755  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.435   1.725  -0.474  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.633   2.507   0.496  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.582   1.023   0.863  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.371  -1.306   0.306  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.252  -2.188  -0.605  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
Download

SMILES for NP0000419 (Cinnamic acid)

OC(=O)\C=C/C1=CC=CC=C1
Download

INCHI for NP0000419 (Cinnamic acid)

InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6-
Download
View in JSmol
Synonyms
ValueSource
(2Z)-3-Phenyl-2-propenoic acidChEBI
(2Z)-3-Phenylacrylic acidChEBI
(Z)-3-Phenyl-2-propenoic acidChEBI
(Z)-Cinnamic acidChEBI
cis-beta-CarboxystyreneChEBI
cis-ZimtsaeureChEBI
(2Z)-3-Phenyl-2-propenoateGenerator
(2Z)-3-PhenylacrylateGenerator
(Z)-3-Phenyl-2-propenoateGenerator
(Z)-CinnamateGenerator
cis-b-CarboxystyreneGenerator
cis-Β-carboxystyreneGenerator
CinnamateGenerator
Cinnamic acid, 1-(13)C-labeled CPDHMDB
Cinnamic acid, 13C-labeled CPDHMDB
trans-Cinnamic acidHMDB
(e)-Cinnamic acid, 2-(14)C-labeled CPDHMDB
Cinnamic acid, (Z)-isomerHMDB
Cinnamic acid, (trans)-(e)-isomerHMDB
Cinnamic acid, 14C-labeled CPDHMDB
Cinnamic acid, 3H-labeled CPD (Z)-isomerHMDB
Cinnamic acid, sodium saltHMDB
Cinnamic acid, sodium salt(Z)-isomerHMDB
Sodium cinnamateHMDB
e-Z Cinnamic acidHMDB
Cinnamic acid, 2-(13)C-labeled CPDHMDB
Cinnamic acid, 2-(14)C-labeled CPDHMDB
Cinnamic acid, 3-(14)C-labeled CPDHMDB
Cinnamic acid, radical ion(1-)HMDB
e-Cinnamic acidHMDB
Cinnamic acid, 1-14C-labeled CPDHMDB
Cinnamic acid, 14C-labeled CPD (e)-isomerHMDB
Cinnamic acid, 3H-labeled CPD (e)-isomerHMDB
Cinnamic acid, ion(1-)HMDB
Cinnamic acid, ion(1-)-(e)-isomerHMDB
Cinnamic acid, nickel (+2) saltHMDB
Cinnamic acid, potassium saltHMDB
Cinnamic acid, sodium salt(e)-isomerHMDB
Cinnamic acid, zinc salt(e)-isomerHMDB
Tritium labeled (e)-cinnamic acidHMDB
Tritium labeled (Z)-cinnamic acidHMDB
(e)-3-Phenyl-2-propenoateHMDB
(e)-3-Phenyl-2-propenoic acidHMDB
3-Phenyl-2-propenoateHMDB
3-Phenyl-2-propenoic acidHMDB
3-Phenyl-acrylateHMDB
3-Phenyl-acrylic acidHMDB
3-PhenylacrylateHMDB
3-Phenylacrylic acidHMDB
3-PhenylpropenoateHMDB
3-Phenylpropenoic acidHMDB
BenzenepropenoateHMDB
Benzenepropenoic acidHMDB
Benzylideneacetic acidHMDB
beta-Phenylacrylic acidHMDB
Cinnamylic acidHMDB
PhenylacrylateHMDB
Phenylacrylic acidHMDB
cis-CinnamateHMDB
(Z)-3-Phenylacrylic acidHMDB
Allocinnamic acidHMDB
Isocinnamic acidHMDB
cis-Cinnamic acidHMDB
Β-phenylacrylic acidHMDB
Cinnamic acidHMDB
Chemical FormulaC9H8O2
Average Mass148.1586 Da
Monoisotopic Mass148.05243 Da
IUPAC Name(2Z)-3-phenylprop-2-enoic acid
Traditional Namecis-cinnamic acid
CAS Registry Number621-82-9
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-SREVYHEPSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Aegle marmelosPlant
Alpinia spp.Plant
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
Artemisia judaicaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica napusPlant
Brassica napus var. napusFooDB
Brassica oleracea var. gongylodesPlant
Brassica oleracea var. italicaFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Catharanthus roseusPlant
CervidaeFooDB
Cervus canadensisFooDB
Cinnamomum aromaticumFooDB
Cinnamomum spp.Plant
Cinnamomum verumFooDB
Cistus ladaniferusPlant
Citrus paradisiPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
ColumbaFooDB
ColumbidaeFooDB
Coriandrum sativum L.FooDB
Curcuma longaFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dioscorea alataPlant
Dromaius novaehollandiaeFooDB
Ephedra sinicaPlant
Equus caballusFooDB
Erigeron breviscapusLOTUS Database
Erythroxylum cocaPlant
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Globularia spp.Plant
Glycine maxPlant
Gynerium sagittatumKNApSAcK Database
Helianthus annuus L.FooDB
Helianthus tuberosusPlant
Isotachis japonicaLOTUS Database
Lagopus mutaFooDB
Laurus nobilis L.FooDB
LeporidaeFooDB
Lepus timidusFooDB
Leucophyllum ambiguumPlant
Lilium candidumPlant
Liquidambar orientalisPlant
Magnolia denudataPlant
Magnolia liliifloraPlant
Malus pumilaFooDB
Medicago sativaPlant
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.Plant
Numida meleagrisFooDB
Ocimum basilicumPlant
OdocoileusFooDB
Olea europaeaFooDB
Origanum vulgareFooDB
OryctolagusFooDB
Ovis ariesFooDB
Paraburkholderia phymatum-
Parthenium argentatumPlant
Phaseolus aureusPlant
PhasianidaeFooDB
Phasianus colchicusFooDB
Piper nigrum L.FooDB
Pisum sativumPlant
Platostoma africanumLOTUS Database
Pleurocybella porrigensFungi
Polygonum minusPlant
Populus spp.Plant
Punica granatumFooDB
Pyrus communisFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Rubus idaeusFooDB
Scrophularia buergerianaPlant
Scrophularia ningpoensisPlant
Scrophularia nodosaPlant
Scrophularia striataPlant
Scrophularia takesimensisPlant
Senna spectabilisPlant
Solanum lycopersicum var. lycopersicumFooDB
Sophora flavescensPlant
Strobilanthes crispusPlant
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syringa persicaLOTUS Database
Tetrapanax papyriferPlant
Thymus capitatusPlant
Thymus vulgarisFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Vaccinium oxycoccosFooDB
Vaccinium vitis-idaeaFooDB
Vitis rupestrisPlant
Vitis vinifera L.FooDB
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 Point132 - 135 °CNot Available
Boiling Point265.00 to 266.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.57 mg/mL at 25 °CNot 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)4.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000567
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012698
KNApSAcK IDC00034743
Chemspider ID10286933
KEGG Compound IDC10438
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinnamic acid
METLIN ID310
PubChem Compound5372954
PDB IDNot Available
ChEBI ID35699
Good Scents IDrw1123131
References
General References
  1. Kukongviriyapan V, Phromsopha N, Tassaneeyakul W, Kukongviriyapan U, Sripa B, Hahnvajanawong V, Bhudhisawasdi V: Inhibitory effects of polyphenolic compounds on human arylamine N-acetyltransferase 1 and 2. Xenobiotica. 2006 Jan;36(1):15-28. [PubMed:16507510 ]
  2. Agnello AM, Combs DB, Filgueiras CC, Willett DS, Mafra-Neto A: Reduced Infestation by Xylosandrus germanus (Coleoptera: Curculionidae: Scolytinae) in Apple Trees Treated with Host Plant Defense Compounds. J Econ Entomol. 2021 Aug 11. pii: 6347851. doi: 10.1093/jee/toab153. [PubMed:34378779 ]
  3. Jantaruk P, Pabuprapap W, Nakaew A, Kunthalert D, Suksamrarn A: 4-methoxybenzalacetone, the cinnamic acid analog as a potential quorum sensing inhibitor against Chromobacterium violaceum and Pseudomonas aeruginosa. World J Microbiol Biotechnol. 2021 Aug 16;37(9):153. doi: 10.1007/s11274-021-03119-x. [PubMed:34398287 ]
  4. Zheng Y, Zhang X, Liu X, Qin N, Xu K, Zeng R, Liu J, Song Y: Nitrogen Supply Alters Rice Defense Against the Striped Stem Borer Chilo suppressalis. Front Plant Sci. 2021 Jul 26;12:691292. doi: 10.3389/fpls.2021.691292. eCollection 2021. [PubMed:34381479 ]
  5. Yang KM, Poolpak T, Pokethitiyook P, Kruatrachue M, Saengwilai P: Responses of oil degrader enzyme activities, metabolism and degradation kinetics to bean root exudates during rhizoremediation of crude oil contaminated soil. Int J Phytoremediation. 2021 Aug 11:1-9. doi: 10.1080/15226514.2021.1926912. [PubMed:34378998 ]
  6. Flachbart LK, Gertzen CGW, Gohlke H, Marienhagen J: Development of a Biosensor Platform for Phenolic Compounds Using a Transition Ligand Strategy. ACS Synth Biol. 2021 Aug 9. doi: 10.1021/acssynbio.1c00165. [PubMed:34369151 ]
  7. Gopalakrishnan S, Ismail A: Aromatic monophenols from cinnamon bark act as proteasome inhibitors by upregulating ER stress, suppressing FoxM1 expression, and inducing apoptosis in prostate cancer cells. Phytother Res. 2021 Aug 6. doi: 10.1002/ptr.7236. [PubMed:34363252 ]
  8. Touzani S, Imtara H, Katekhaye S, Mechchate H, Ouassou H, Alqahtani AS, Noman OM, Nasr FA, Fearnley H, Fearnley J, Paradkar A, ElArabi I, Lyoussi B: Determination of Phenolic Compounds in Various Propolis Samples Collected from an African and an Asian Region and Their Impact on Antioxidant and Antibacterial Activities. Molecules. 2021 Jul 29;26(15). pii: molecules26154589. doi: 10.3390/molecules26154589. [PubMed:34361742 ]
  9. Kimani BG, Kerekes EB, Szebenyi C, Krisch J, Vagvolgyi C, Papp T, Tako M: In Vitro Activity of Selected Phenolic Compounds against Planktonic and Biofilm Cells of Food-Contaminating Yeasts. Foods. 2021 Jul 17;10(7). pii: foods10071652. doi: 10.3390/foods10071652. [PubMed:34359522 ]
  10. Nguyen PD, Sayagh C, Massiot G, Lavaud C: Phenyl glycosides from the leaves of Flacourtia indica (Burm. f.) Merr (Salicaceae). Phytochemistry. 2021 Aug 3;190:112891. doi: 10.1016/j.phytochem.2021.112891. [PubMed:34358899 ]
  11. Tyagi A, Shabbir U, Chelliah R, Daliri EB, Chen X, Oh DH: Limosilactobacillus reuteri Fermented Brown Rice: A Product with Enhanced Bioactive Compounds and Antioxidant Potential. Antioxidants (Basel). 2021 Jul 5;10(7). pii: antiox10071077. doi: 10.3390/antiox10071077. [PubMed:34356310 ]
  12. Abbasi S, Higashino H, Sato Y, Minami K, Kataoka M, Yamashita S, Harashima H: Maximizing the Oral Bioavailability of Poorly Water-Soluble Drugs Using Novel Oil-Like Materials in Lipid-Based Formulations. Mol Pharm. 2021 Aug 5. doi: 10.1021/acs.molpharmaceut.1c00197. [PubMed:34351769 ]
  13. Kalb V, Seewald T, Hofmann T, Granvogl M: Investigations into the Ability to Reduce Cinnamic Acid as Undesired Precursor of Toxicologically Relevant Styrene in Wort by Different Barley to Wheat Ratios (Grain Bill) during Mashing. J Agric Food Chem. 2021 Aug 18;69(32):9443-9450. doi: 10.1021/acs.jafc.1c03018. Epub 2021 Aug 5. [PubMed:34351749 ]