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Showing metabocard for 4-Methoxycinnamic acid (HMDB0002040)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2023-02-21 17:16:05 UTC
HMDB IDHMDB0002040
Secondary Accession Numbers
  • HMDB02040
Metabolite Identification
Common Name4-Methoxycinnamic acid
Description4-Methoxycinnamic acid, also known as para-methoxycinnamate or O-methyl-p-coumarate, 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. Outside of the human body, 4-Methoxycinnamic acid is found, on average, in the highest concentration within turmerics. 4-Methoxycinnamic acid has also been detected, but not quantified in cow milk and wild celeries. This could make 4-methoxycinnamic acid a potential biomarker for the consumption of these foods.
Structure
Data?1676999765
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002040 (4-Methoxycinnamic acid)


  Mrv1652306141922352D          

 13 13  0  0  0  0            999 V2000
    1.7862    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -0.2061    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
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
  9 10  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
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3D MOL for HMDB0002040 (4-Methoxycinnamic acid)

HMDB0002040
     RDKit          3D
4-Methoxycinnamic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -4.2689    0.5623    0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5344   -0.5471    0.4335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630   -0.5223    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147   -1.6741   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532   -1.6886   -0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6270   -0.5427   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689   -0.5964   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    0.4221   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.2955   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -0.7802   -0.9183 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1367    1.3864   -0.3571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574    0.5683    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4112    0.6039    0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    0.6204    1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3516    0.4846    0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9253    1.5132    0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0983   -2.5827   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -2.5720   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435   -1.5231   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729    1.3604    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768    2.2349    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    1.4764    0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292    1.5009    0.7630 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 13  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
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3D SDF for HMDB0002040 (4-Methoxycinnamic acid)


  Mrv1652306141922352D          

 13 13  0  0  0  0            999 V2000
    1.7862    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -0.2061    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
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
  9 10  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002040

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(\C=C\C(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+

> <INCHI_KEY>
AFDXODALSZRGIH-QPJJXVBHSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.34403874731484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-methoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.978414994333333

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.109550179068184

> <JCHEM_PKA_STRONGEST_BASIC>
-4.823943867272176

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
49.523100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-methoxy-cinnamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002040 (4-Methoxycinnamic acid)

HMDB0002040
     RDKit          3D
4-Methoxycinnamic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -4.2689    0.5623    0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5344   -0.5471    0.4335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630   -0.5223    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147   -1.6741   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532   -1.6886   -0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6270   -0.5427   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689   -0.5964   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    0.4221   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.2955   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -0.7802   -0.9183 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1367    1.3864   -0.3571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574    0.5683    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4112    0.6039    0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    0.6204    1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3516    0.4846    0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9253    1.5132    0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0983   -2.5827   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3785   -2.5720   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435   -1.5231   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729    1.3604    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768    2.2349    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    1.4764    0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292    1.5009    0.7630 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 13  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
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PDB for HMDB0002040 (4-Methoxycinnamic acid)

HEADER    PROTEIN                                 14-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JUN-19         0                                  
HETATM    1  C   UNK     0       3.334   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.000  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.668   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.002   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.336   1.925   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.336   3.465   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.669   1.155   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.667  -1.155   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0002040 (4-Methoxycinnamic acid)

COMPND    HMDB0002040
HETATM    1  C1  UNL     1      -4.269   0.562   0.859  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.534  -0.547   0.434  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.163  -0.522   0.229  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.515  -1.674  -0.195  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.153  -1.689  -0.408  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.627  -0.543  -0.206  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.069  -0.596  -0.443  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.890   0.422  -0.283  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.312   0.295  -0.537  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.821  -0.780  -0.918  1.00  0.00           O  
HETATM   11  O3  UNL     1       5.137   1.386  -0.357  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.057   0.568   0.212  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.411   0.604   0.431  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.216   0.620   1.951  1.00  0.00           H  
HETATM   15  H2  UNL     1      -5.352   0.485   0.586  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.925   1.513   0.355  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.098  -2.583  -0.361  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.379  -2.572  -0.739  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.544  -1.523  -0.777  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.473   1.360   0.046  1.00  0.00           H  
HETATM   21  H8  UNL     1       4.877   2.235   0.113  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.496   1.476   0.383  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.929   1.501   0.763  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7   12
CONECT    7    8    8   19
CONECT    8    9   20
CONECT    9   10   10   11
CONECT   11   21
CONECT   12   13   13   22
CONECT   13   23
END
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SMILES for HMDB0002040 (4-Methoxycinnamic acid)

COC1=CC=C(\C=C\C(O)=O)C=C1
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INCHI for HMDB0002040 (4-Methoxycinnamic acid)

InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-MethoxycinnamateGenerator
3-(4-Methoxyphenyl)acrylic acidChEMBL, HMDB
Para-methoxycinnamic acidChEMBL, HMDB
3-(4-Methoxyphenyl)acrylateGenerator, HMDB
Para-methoxycinnamateGenerator, HMDB
(e)-3-(4-Methoxyphenyl)acrylateHMDB
(e)-3-(4-Methoxyphenyl)acrylic acidHMDB
3-(4-Methoxy-phenyl)-acrylateHMDB
3-(4-Methoxy-phenyl)-acrylic acidHMDB
3-(4-Methoxyphenyl)-2-propenoateHMDB
3-(4-Methoxyphenyl)-2-propenoic acidHMDB
4-Methoxy cinnamateHMDB
4-Methoxy cinnamic acidHMDB
O-Methyl-P-coumarateHMDB
O-Methyl-P-coumaric acidHMDB
P-Hydroxy methyl cinnamateHMDB
P-Methoxy ciannamateHMDB
P-Methoxy ciannamic acidHMDB
P-MethoxycinnamateHMDB
P-Methoxycinnamic acidHMDB
trans-4-MethoxycinnamateHMDB
trans-4-Methoxycinnamic acidHMDB
4-Methoxycinnamate, aluminum saltMeSH, HMDB
4-Methoxycinnamate, (e)-isomerMeSH, HMDB
4-Methoxycinnamate, (Z)-isomerMeSH, HMDB
4-Methoxycinnamate, zinc saltMeSH, HMDB
4-Methoxycinnamate, zirconium saltMeSH, HMDB
e-P-Methoxycinnamic acidMeSH, HMDB
4-Methoxycinnamate, calcium saltMeSH, HMDB
4-Methoxycinnamate, magnesium saltMeSH, HMDB
4-Methoxycinnamate, potassium saltMeSH, HMDB
4-Methoxycinnamate, sodium saltMeSH, HMDB
(2E)-3-(4-Methoxyphenyl)prop-2-enoateGenerator, HMDB
4-Methoxycinnamic acidMeSH
(2E)-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
(E)-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
(E)-3-(4-Methoxyphenyl)acrylic acidHMDB
(E)-4-Methoxycinnamic acidHMDB
(E)-p-Methoxycinnamic acidHMDB
3-(4-Methoxyphenyl)propenoic acidHMDB
4'-Methoxycinnamic acidHMDB
4-Methyoxycinnamic acidHMDB
4’-Methoxycinnamic acidHMDB
O-Methyl-p-coumaric acidHMDB
p-Methoxycinnamic acidHMDB
trans-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
trans-p-Methoxycinnamic acidHMDB
trans-p-MethoxycinnamateGenerator, HMDB
Chemical FormulaC10H10O3
Average Molecular Weight178.1846
Monoisotopic Molecular Weight178.062994186
IUPAC Name(2E)-3-(4-methoxyphenyl)prop-2-enoic acid
Traditional Namep-methoxy-cinnamic acid
CAS Registry Number943-89-5
SMILES
COC1=CC=C(\C=C\C(O)=O)C=C1
InChI Identifier
InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+
InChI KeyAFDXODALSZRGIH-QPJJXVBHSA-N
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
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point173 - 175 °CNot Available
Boiling Point342.59 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.71 mg/mL at 25 °CNot Available
LogP2.68HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg146.27930932474
[M+H]+MetCCS_train_pos140.84930932474
[M-H]-Not Available146.279http://allccs.zhulab.cn/database/detail?ID=AllCCS00000433
[M+H]+Not Available141.375http://allccs.zhulab.cn/database/detail?ID=AllCCS00000433
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
logP2.37ALOGPS
logP1.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.11ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.52 m³·mol⁻¹ChemAxon
Polarizability18.34 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
DarkChem[M+H]+142.3131661259
DarkChem[M-H]-141.87831661259
DeepCCS[M+H]+140.28830932474
DeepCCS[M-H]-137.91630932474
DeepCCS[M-2H]-173.13930932474
DeepCCS[M+Na]+148.4530932474
AllCCS[M+H]+138.232859911
AllCCS[M+H-H2O]+133.932859911
AllCCS[M+NH4]+142.232859911
AllCCS[M+Na]+143.332859911
AllCCS[M-H]-138.332859911
AllCCS[M+Na-2H]-139.132859911
AllCCS[M+HCOO]-140.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.13 minutes32390414
Predicted by Siyang on May 30, 202212.1115 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.14 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1864.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid387.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid150.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid236.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid164.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid455.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid463.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)112.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1084.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid402.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1080.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid280.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid372.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate403.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA334.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water32.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Methoxycinnamic acidCOC1=CC=C(\C=C\C(O)=O)C=C13147.1Standard polar33892256
4-Methoxycinnamic acidCOC1=CC=C(\C=C\C(O)=O)C=C11638.9Standard non polar33892256
4-Methoxycinnamic acidCOC1=CC=C(\C=C\C(O)=O)C=C11776.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Methoxycinnamic acid,1TMS,isomer #1COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C)C=C11834.6Semi standard non polar33892256
4-Methoxycinnamic acid,1TBDMS,isomer #1COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)C=C12088.7Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.693 +/- 0.228 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.475 +/- 0.218 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.752 +/- 0.225 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.762 +/- 0.324 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.52 +/- 0.192 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.555 +/- 0.17 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.435 +/- 0.204 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified2.941 +/- 2.612 uMAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.02 +/- 0.006 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002667
KNApSAcK IDNot Available
Chemspider ID609479
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6453
PubChem Compound699414
PDB IDNot Available
ChEBI ID260249
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1417131
References
Synthesis ReferencePuscaru, E.; Zotta, V.; Serper, Ana; Popescu, Margareta; Hociung, Jana; Gasmet, Ana; Spataru, Rodica. The N-methyl series of piperazine. II. Cinnamic acid derivatives. Farmacia (Bucharest, Romania) (1961), 9 345-50.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Methoxycinnamic acid → 3,4,5-trihydroxy-6-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic aciddetails