You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:50:48 UTC

Update Date

2021-09-07 17:05:32 UTC

HMDB ID

HMDB0032616

Secondary Accession Numbers

HMDB32616

Metabolite Identification

Common Name

Sinapic acid

Description

Sinapic acid, also known as sinapinate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Sinapic acid has been detected, but not quantified, in several different foods, such as strawberry guava, purple lavers, common verbena, ryes, and lupines. This could make sinapic acid a potential biomarker for the consumption of these foods. A sinapic acid in which the double bond has trans-configuration.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306171921372D          

 16 16  0  0  0  0            999 V2000
   -1.6293   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440   -1.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6293   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -0.5024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730   -1.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440   -2.5653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0585   -2.9777    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  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  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
 10 12  1  0  0  0  0
  3  7  1  0  0  0  0
  4 13  1  0  0  0  0
  7 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032616

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+

> <INCHI_KEY>
PCMORTLOPMLEFB-ONEGZZNKSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.21

> <EXACT_MASS>
224.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.323224439789968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.5171784069999998

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.405618194181288

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.606694294741961

> <JCHEM_PKA_STRONGEST_BASIC>
-4.604716708653556

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
57.967200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sinapinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/COC1=CC(%5CC=C%5CC(O)=O)=CC(OC)...
 OpenBabel09142113243D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:27})
 28 28  0  0  0  0  0  0  0  0999 V2000
    2.6308    3.2901    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    1.9197    0.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486    0.9842    0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244    1.3785    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.4150    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    0.8304   -0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792   -0.1011   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0392    0.2997   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -0.6306   -0.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3248    1.4821   -0.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -0.9450    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662   -1.3317    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884   -2.6531    0.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051   -3.5849    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3737   -0.3701    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774   -0.7542    0.0085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    3.9297    0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0370    3.4916   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0332    3.4943    0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4729    2.4289    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542    1.8802   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -1.1508    0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9105   -0.2618   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410   -1.6912    0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074   -3.4314    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -3.4334   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999   -4.6009    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -0.8699   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  2  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  7 22  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 23  1  0  0  0  0
 11 12  1  0  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  2  0  0  0  0
 13 14  1  0  0  0  0
 14 25  1  0  0  0  0
 14 26  1  0  0  0  0
 14 27  1  0  0  0  0
 15 16  1  0  0  0  0
 16 28  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 17-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.043  -0.168   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.960   1.372   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.294  -0.938   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -7.043  -3.248   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.377  -0.938   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.375  -4.789   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.709  -5.558   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    1                                                       
CONECT    7    3   14                                                       
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    4                                                            
CONECT   14    7                                                            
CONECT   15    5   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/COC1=CC(%5CC=C%5CC(O)=O)=CC(OC)... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       2.631   3.290   0.006  1.00  0.00           C  
HETATM    2  O   UNL     1       3.036   1.920   0.009  1.00  0.00           O  
HETATM    3  C   UNL     1       2.049   0.984   0.009  1.00  0.00           C  
HETATM    4  C   UNL     1       0.724   1.379   0.005  1.00  0.00           C  
HETATM    5  C   UNL     1      -0.291   0.415   0.004  1.00  0.00           C  
HETATM    6  C   UNL     1      -1.701   0.830  -0.000  1.00  0.00           C  
HETATM    7  C   UNL     1      -2.679  -0.101  -0.001  1.00  0.00           C  
HETATM    8  C   UNL     1      -4.039   0.300  -0.005  1.00  0.00           C  
HETATM    9  O   UNL     1      -5.017  -0.631  -0.006  1.00  0.00           O  
HETATM   10  O   UNL     1      -4.325   1.482  -0.008  1.00  0.00           O  
HETATM   11  C   UNL     1       0.040  -0.945   0.006  1.00  0.00           C  
HETATM   12  C   UNL     1       1.366  -1.332   0.010  1.00  0.00           C  
HETATM   13  O   UNL     1       1.688  -2.653   0.012  1.00  0.00           O  
HETATM   14  C   UNL     1       0.605  -3.585   0.011  1.00  0.00           C  
HETATM   15  C   UNL     1       2.374  -0.370   0.005  1.00  0.00           C  
HETATM   16  O   UNL     1       3.677  -0.754   0.009  1.00  0.00           O  
HETATM   17  H   UNL     1       3.513   3.930   0.007  1.00  0.00           H  
HETATM   18  H   UNL     1       2.037   3.492  -0.885  1.00  0.00           H  
HETATM   19  H   UNL     1       2.033   3.494   0.895  1.00  0.00           H  
HETATM   20  H   UNL     1       0.473   2.429   0.004  1.00  0.00           H  
HETATM   21  H   UNL     1      -1.954   1.880  -0.002  1.00  0.00           H  
HETATM   22  H   UNL     1      -2.426  -1.151   0.001  1.00  0.00           H  
HETATM   23  H   UNL     1      -5.910  -0.262  -0.009  1.00  0.00           H  
HETATM   24  H   UNL     1      -0.741  -1.691   0.006  1.00  0.00           H  
HETATM   25  H   UNL     1      -0.007  -3.431   0.899  1.00  0.00           H  
HETATM   26  H   UNL     1      -0.003  -3.433  -0.881  1.00  0.00           H  
HETATM   27  H   UNL     1       1.000  -4.601   0.013  1.00  0.00           H  
HETATM   28  H   UNL     1       4.055  -0.870  -0.874  1.00  0.00           H  
CONECT    1    2   17   18   19                                       
CONECT    2    1    3                                                 
CONECT    3    2    4    4   15                                       
CONECT    4    3    3    5   20                                       
CONECT    5    4    6   11   11                                       
CONECT    6    5    7    7   21                                       
CONECT    7    6    6    8   22                                       
CONECT    8    7    9   10   10                                       
CONECT    9    8   23                                                 
CONECT   10    8    8                                                 
CONECT   11    5    5   12   24                                       
CONECT   12   11   13   15   15                                       
CONECT   13   12   14                                                 
CONECT   14   13   25   26   27                                       
CONECT   15   12   12    3   16                                       
CONECT   16   15   28                                                 
CONECT   17    1                                                      
CONECT   18    1                                                      
CONECT   19    1                                                      
CONECT   20    4                                                      
CONECT   21    6                                                      
CONECT   22    7                                                      
CONECT   23    9                                                      
CONECT   24   11                                                      
CONECT   25   14                                                      
CONECT   26   14                                                      
CONECT   27   14                                                      
CONECT   28   16                                                      
MASTER        0    0    0    0    0    0    0    0   28    0   28    0
END

https://cactus.nci.nih.gov/chemical/structure/COC1=CC(%5CC=C%5CC(O)=O)=CC(OC)...
 OpenBabel09142113243D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:27})
 28 28  0  0  0  0  0  0  0  0999 V2000
    2.6308    3.2901    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    1.9197    0.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486    0.9842    0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244    1.3785    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.4150    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    0.8304   -0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792   -0.1011   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0392    0.2997   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -0.6306   -0.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3248    1.4821   -0.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -0.9450    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662   -1.3317    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884   -2.6531    0.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051   -3.5849    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3737   -0.3701    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774   -0.7542    0.0085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134    3.9297    0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0370    3.4916   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0332    3.4943    0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4729    2.4289    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542    1.8802   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -1.1508    0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9105   -0.2618   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410   -1.6912    0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074   -3.4314    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -3.4334   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999   -4.6009    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -0.8699   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  2  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  7 22  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 23  1  0  0  0  0
 11 12  1  0  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  2  0  0  0  0
 13 14  1  0  0  0  0
 14 25  1  0  0  0  0
 14 26  1  0  0  0  0
 14 27  1  0  0  0  0
 15 16  1  0  0  0  0
 16 28  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	ChEBI
SINAPINATE	ChEBI
Sinapinic acid	ChEBI
3,5-Dimethoxy-4-hydroxycinnamic acid	Kegg
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoate	Generator
3,5-Dimethoxy-4-hydroxycinnamate	Generator
Sinapate	Generator
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid	HMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(2E)-2-propenoic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(e)-2-propenoic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid	HMDB
4-Hydroxy-3,5-dimethoxy-(e)-cinnamic acid	HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid	HMDB
trans-3,5-Dimethoxy-4-hydroxycinnamic acid	HMDB
trans-Sinapate	HMDB
(e)-Sinapic acid	HMDB
Synapitic acid	HMDB
trans-Sinapinic acid	HMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acid	HMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid	HMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid	HMDB
e-Sinapinic acid	HMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid	HMDB
trans-Sinapic acid	HMDB
Sinapic acid	ChEBI

Chemical Formula

C₁₁H₁₂O₅

Average Molecular Weight

224.21

Monoisotopic Molecular Weight

224.068473494

IUPAC Name

(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

Traditional Name

sinapinic acid

CAS Registry Number

7362-37-0

SMILES

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+

InChI Key

PCMORTLOPMLEFB-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid (CHEBI:15714 )
Sinapate derivatives (C00482 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	192 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.97 m³·mol⁻¹	ChemAxon
Polarizability	22.32 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Sinapic acid,1TMS,#1	2214.299	https://arxiv.org/abs/1905.12712
Sinapic acid,1TMS,#2	2169.7712	https://arxiv.org/abs/1905.12712
Sinapic acid,2TMS,#1	2201.4788	https://arxiv.org/abs/1905.12712
Sinapic acid,1TBDMS,#1	2477.673	https://arxiv.org/abs/1905.12712
Sinapic acid,1TBDMS,#2	2451.1287	https://arxiv.org/abs/1905.12712
Sinapic acid,2TBDMS,#1	2735.2854	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00kr-3759000000-26099df97cd2adef2dc3	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-4390000000-ce04c31c3e4023faa7ee	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kr-2759000000-404687968a18ced29cd9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kr-1869000000-618d42ab9681ecb06228	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9535000000-dc1aa60962d61ce2d9bb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9636000000-15691f6a00fd74dadf7a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00kr-3759000000-26099df97cd2adef2dc3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-1966000000-84b6d21b3c65f74d1b2d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05di-1950000000-308e223e0595ec83666c	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0umi-8196000000-afceb35e7a5f28ec225c	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-5590000000-92339c0e84f7bfd7f855	2015-03-01	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-002e-0900000000-c7f7d78d04b4c61a02e1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0007-0900000000-76cfe991af651e6cec19	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0290000000-475d3684fdd4228e9c5d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-08fr-0940000000-780771eea370a78b609a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-1900000000-3e127fbdcf11519a02f3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00dl-3900000000-d41ed2853570e017a98c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-006x-9600000000-668bfef76d2c29514216	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-1950000000-845dcc12144449b6b8c5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-074m-1940000000-4eaf9a539449ae53a970	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-1590000000-f69ac29a002b25accd73	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ar4-3940000000-64d09640303051f3b774	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-9500000000-8fb01ded8d8100c7badf	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-9100000000-6b4758d6474e1684747b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00dl-2900000000-512d339f4cd5c1a36d79	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-2900000000-f1f1c513515bb228b410	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-08mm-0930000000-725b42822634411b06e1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0190000000-6e81a94093485194a43f	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1960000000-18717b9e874f0901ea68	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06vj-2900000000-254ee08e710708eb6545	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0190000000-89ae701e731ef1f24fd7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0890000000-74c0bdbe7769b328017a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1910000000-69bbc48ce24397a342a2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0290000000-9de305bfb1242c5c3e10	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0980000000-368fb5936979c9a6e99d	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-3900000000-395e080ff0323f7c60bc	2021-09-07	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)	2015-03-12	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 464	12771321	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 464	12592675	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 464	14733499	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB08587

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Sinapinic_acid

METLIN ID

Not Available

PubChem Compound

637775

PDB ID

Not Available

ChEBI ID

15714

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yun KJ, Koh DJ, Kim SH, Park SJ, Ryu JH, Kim DG, Lee JY, Lee KT: Anti-inflammatory effects of sinapic acid through the suppression of inducible nitric oxide synthase, cyclooxygase-2, and proinflammatory cytokines expressions via nuclear factor-kappaB inactivation. J Agric Food Chem. 2008 Nov 12;56(21):10265-72. doi: 10.1021/jf802095g. Epub 2008 Oct 9. [PubMed:18841975 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Sinapic acid (HMDB0032616)

MOL for HMDB0032616 (Sinapic acid)

3D MOL for HMDB0032616 (Sinapic acid)

3D SDF for HMDB0032616 (Sinapic acid)

3D-SDF for HMDB0032616 (Sinapic acid)

PDB for HMDB0032616 (Sinapic acid)

3D PDB for HMDB0032616 (Sinapic acid)

SMILES for HMDB0032616 (Sinapic acid)

INCHI for HMDB0032616 (Sinapic acid)

Structure for HMDB0032616 (Sinapic acid)

3D Structure for HMDB0032616 (Sinapic acid)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR