Showing metabocard for Cinnamic acid (MMDBc0048010)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-19 21:49:38 UTC
Update Date2024-04-30 20:34:59 UTC
Metabolite IDMMDBc0048010
Metabolite 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005634c28bca70>


  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
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3D MOL for #<Metabolite:0x00005634c28bca70>

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
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3D SDF for #<Metabolite:0x00005634c28bca70>


  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>
MMDBc0048010

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00005634c28bca70>

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
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PDB for #<Metabolite:0x00005634c28bca70>

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
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3D PDB for #<Metabolite:0x00005634c28bca70>

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
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SMILES for #<Metabolite:0x00005634c28bca70>

OC(=O)\C=C/C1=CC=CC=C1
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INCHI for #<Metabolite:0x00005634c28bca70>

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
(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
Molecular FormulaC9H8O2
Average Mass148.1586
Monoisotopic Mass148.0524295
IUPAC Name(2Z)-3-phenylprop-2-enoic acid
Traditional Namecis-cinnamic acid
CAS Registry NumberNot Available
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