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Showing metabocard for Sinapic acid (HMDB0032616)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:50:48 UTC
Update Date2022-03-07 02:53:24 UTC
HMDB IDHMDB0032616
Secondary Accession Numbers
  • HMDB32616
Metabolite Identification
Common NameSinapic acid
DescriptionSinapic 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 is an odorless tasting compound. Sinapic acid is found, on average, in the highest concentration within a few different foods, such as sunflowers (Helianthus annuus), olives (Olea europaea), and garden onions (Allium cepa) and in a lower concentration in hard wheats (Triticum durum), rapes (Brassica napus var. napus), and garlics (Allium sativum). Sinapic acid has also been detected, but not quantified in, several different foods, such as chives (Allium schoenoprasum), teffs (Eragrostis tef), celeriacs (Apium graveolens var. rapaceum), yardlong beans (Vigna unguiculata ssp. sesquipedalis), and pepper (c. pubescens). This could make sinapic acid a potential biomarker for the consumption of these foods. Sinapic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Sinapic acid.
Structure
Data?1588108290
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032616 (Sinapic acid)


  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
Download

3D MOL for HMDB0032616 (Sinapic acid)

HMDB0032616
     RDKit          3D
Sinapic acid
 28 28  0  0  0  0  0  0  0  0999 V2000
   -1.4704    3.9531   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    2.7505   -0.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    1.5485   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1109    1.5164   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5648    0.2945    0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0129    0.3261    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -0.7564    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -0.6209    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024    0.4838    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0029   -1.7620    0.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617   -0.8714   -0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498   -0.8729   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -2.0321   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786   -3.3252   -0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1728    0.3540   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5684    0.3441   -0.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1474    4.8278   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8270    3.9900   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    3.9131    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442    2.4432    0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516    1.2877    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129   -1.7379    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6456   -2.6692    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225   -1.8397   -0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900   -3.9827    0.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -3.7185   -1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9220   -3.3643    0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1137   -0.4798   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15  3  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 10 23  1  0
 11 24  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
 16 28  1  0
M  END
Download

3D SDF for HMDB0032616 (Sinapic acid)


  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

$$$$
Download

3D-SDF for HMDB0032616 (Sinapic acid)

HMDB0032616
     RDKit          3D
Sinapic acid
 28 28  0  0  0  0  0  0  0  0999 V2000
   -1.4704    3.9531   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    2.7505   -0.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    1.5485   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1109    1.5164   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5648    0.2945    0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0129    0.3261    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -0.7564    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -0.6209    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024    0.4838    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0029   -1.7620    0.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617   -0.8714   -0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498   -0.8729   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -2.0321   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786   -3.3252   -0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1728    0.3540   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5684    0.3441   -0.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1474    4.8278   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8270    3.9900   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    3.9131    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442    2.4432    0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516    1.2877    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129   -1.7379    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6456   -2.6692    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225   -1.8397   -0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900   -3.9827    0.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -3.7185   -1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9220   -3.3643    0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1137   -0.4798   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 15  3  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
 10 23  1  0
 11 24  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
 16 28  1  0
M  END
Download

PDB for HMDB0032616 (Sinapic acid)

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
Download

3D PDB for HMDB0032616 (Sinapic acid)

COMPND    HMDB0032616
HETATM    1  C1  UNL     1      -1.470   3.953  -0.140  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.193   2.751  -0.198  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.485   1.549  -0.144  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.111   1.516  -0.037  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.565   0.295   0.014  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.013   0.326   0.127  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.764  -0.756   0.184  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.222  -0.621   0.298  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.802   0.484   0.344  1.00  0.00           O  
HETATM   10  O3  UNL     1       5.003  -1.762   0.357  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.162  -0.871  -0.044  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.550  -0.873  -0.152  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.278  -2.032  -0.210  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.779  -3.325  -0.173  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.173   0.354  -0.199  1.00  0.00           C  
HETATM   16  O5  UNL     1      -3.568   0.344  -0.308  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.147   4.828  -0.100  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.827   3.990  -1.061  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.836   3.913   0.771  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.444   2.443   0.007  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.552   1.288   0.170  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.313  -1.738   0.148  1.00  0.00           H  
HETATM   23  H7  UNL     1       4.646  -2.669   0.629  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.323  -1.840  -0.007  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.590  -3.983   0.258  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.439  -3.718  -1.151  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.922  -3.364   0.531  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.114  -0.480  -0.351  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   15
CONECT    4    5   20
CONECT    5    6   11   11
CONECT    6    7    7   21
CONECT    7    8   22
CONECT    8    9    9   10
CONECT   10   23
CONECT   11   12   24
CONECT   12   13   15   15
CONECT   13   14
CONECT   14   25   26   27
CONECT   15   16
CONECT   16   28
END
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SMILES for HMDB0032616 (Sinapic acid)

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O
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INCHI for HMDB0032616 (Sinapic acid)

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+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidChEBI
SINAPINATEChEBI
Sinapinic acidChEBI
3,5-Dimethoxy-4-hydroxycinnamic acidKegg
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoateGenerator
3,5-Dimethoxy-4-hydroxycinnamateGenerator
SinapateGenerator
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidHMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acidHMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(2E)-2-propenoic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(e)-2-propenoic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acidHMDB
4-Hydroxy-3,5-dimethoxy-(e)-cinnamic acidHMDB
4-Hydroxy-3,5-dimethoxycinnamic acidHMDB
trans-3,5-Dimethoxy-4-hydroxycinnamic acidHMDB
Sinapic acidChEBI
trans-SinapateGenerator, HMDB
(e)-Sinapic acidMeSH, HMDB
Synapitic acidMeSH, HMDB
trans-Sinapinic acidMeSH, HMDB
(E)-3,5-Dimethoxy-4-hydroxycinnamic acidHMDB
(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acidHMDB
(E)-Sinapic acidHMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acidHMDB
E-Sinapinic acidHMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acidHMDB
trans-Sinapic acidHMDB
Chemical FormulaC11H12O5
Average Molecular Weight224.21
Monoisotopic Molecular Weight224.068473494
IUPAC Name(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
Traditional Namesinapinic acid
CAS Registry Number7362-37-0
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 KeyPCMORTLOPMLEFB-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
  • 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid (CHEBI:15714 )
  • Sinapate derivatives (C00482 )
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Biological roleIndirect biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point192 °CNot Available
Boiling Point403.41 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility7082 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.286 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.63 g/LALOGPS
logP1.63ALOGPS
logP1.52ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.97 m³·mol⁻¹ChemAxon
Polarizability22.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+152.60130932474
DeepCCS[M-H]-150.24330932474
DeepCCS[M-2H]-183.72930932474
DeepCCS[M+Na]+158.7230932474
AllCCS[M+H]+149.632859911
AllCCS[M+H-H2O]+145.632859911
AllCCS[M+NH4]+153.332859911
AllCCS[M+Na]+154.332859911
AllCCS[M-H]-148.232859911
AllCCS[M+Na-2H]-148.632859911
AllCCS[M+HCOO]-149.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sinapic acidCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1O3815.2Standard polar33892256
Sinapic acidCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1O2004.3Standard non polar33892256
Sinapic acidCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1O2149.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sinapic acid,1TMS,isomer #1COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1O2214.3Semi standard non polar33892256
Sinapic acid,1TMS,isomer #2COC1=CC(/C=C/C(=O)O)=CC(OC)=C1O[Si](C)(C)C2169.8Semi standard non polar33892256
Sinapic acid,2TMS,isomer #1COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C2201.5Semi standard non polar33892256
Sinapic acid,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O2477.7Semi standard non polar33892256
Sinapic acid,1TBDMS,isomer #2COC1=CC(/C=C/C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C2451.1Semi standard non polar33892256
Sinapic acid,2TBDMS,isomer #1COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C2735.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Sinapic acid GC-MS (2 TMS)splash10-00kr-3759000000-26099df97cd2adef2dc32014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapic acid EI-B (Non-derivatized)splash10-00di-4390000000-ce04c31c3e4023faa7ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized)splash10-00kr-2759000000-404687968a18ced29cd92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized)splash10-00kr-1869000000-618d42ab9681ecb062282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized)splash10-00di-9535000000-dc1aa60962d61ce2d9bb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized)splash10-00di-9636000000-15691f6a00fd74dadf7a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapic acid GC-MS (Non-derivatized)splash10-00kr-3759000000-26099df97cd2adef2dc32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapic acid GC-EI-TOF (Non-derivatized)splash10-000i-1966000000-84b6d21b3c65f74d1b2d2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinapic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-05di-1950000000-308e223e0595ec83666c2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinapic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0umi-8196000000-afceb35e7a5f28ec225c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinapic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-5590000000-92339c0e84f7bfd7f8552015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid DI-ESI-qTof , Positive-QTOFsplash10-002e-0900000000-c7f7d78d04b4c61a02e12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid DI-ESI-qTof , Negative-QTOFsplash10-0007-0900000000-76cfe991af651e6cec192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOFsplash10-00di-0290000000-475d3684fdd4228e9c5d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOFsplash10-08fr-0940000000-780771eea370a78b609a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOFsplash10-0002-1900000000-3e127fbdcf11519a02f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOFsplash10-00dl-3900000000-d41ed2853570e017a98c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QQ , negative-QTOFsplash10-006x-9600000000-668bfef76d2c295142162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QTOF , negative-QTOFsplash10-00di-1950000000-845dcc12144449b6b8c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QTOF , negative-QTOFsplash10-074m-1940000000-4eaf9a539449ae53a9702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QTOF , positive-QTOFsplash10-0a4i-1590000000-f69ac29a002b25accd732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid LC-ESI-QTOF , positive-QTOFsplash10-0ar4-3940000000-64d09640303051f3b7742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOFsplash10-0006-9500000000-8fb01ded8d8100c7badf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOFsplash10-0006-9100000000-6b4758d6474e1684747b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOFsplash10-00dl-2900000000-512d339f4cd5c1a36d792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOFsplash10-00di-2900000000-f1f1c513515bb228b4102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOFsplash10-08mm-0930000000-725b42822634411b06e12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid 6V, Positive-QTOFsplash10-00kf-9400000000-e70224cdae252d3c8e182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid 40V, Positive-QTOFsplash10-0006-9200000000-45fe03024d3082fc695e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapic acid 20V, Negative-QTOFsplash10-0btc-0940000000-61107acc0e4d467950bf2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapic acid 10V, Positive-QTOFsplash10-056r-0190000000-6e81a94093485194a43f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapic acid 20V, Positive-QTOFsplash10-004i-1960000000-18717b9e874f0901ea682016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapic acid 40V, Positive-QTOFsplash10-06vj-2900000000-254ee08e710708eb65452016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapic acid 10V, Negative-QTOFsplash10-00di-0190000000-89ae701e731ef1f24fd72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapic acid 20V, Negative-QTOFsplash10-00di-0890000000-74c0bdbe7769b328017a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapic acid 40V, Negative-QTOFsplash10-0a4i-1910000000-69bbc48ce24397a342a22016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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
DrugBank IDDB08587
Phenol Explorer Compound ID464
FooDB IDFDB010557
KNApSAcK IDC00002776
Chemspider ID553361
KEGG Compound IDC00482
BioCyc IDSINAPATE
BiGG IDNot Available
Wikipedia LinkSinapinic_acid
METLIN IDNot Available
PubChem Compound637775
PDB IDNot Available
ChEBI ID15714
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1548161
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .