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Showing NP-Card for 3-Hydroxy-4-methoxycinnamic acid (NP0331730)

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Record Information
Version2.0
Created at2023-07-25 00:01:22 UTC
Updated at2024-09-03 04:16:40 UTC
NP-MRD IDNP0331730
Natural Product DOIhttps://doi.org/10.57994/0755
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxy-4-methoxycinnamic acid
DescriptionIsoferulic acid, also known as hesperetic acid or isoferulate, 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. Isoferulic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3-Hydroxy-4-methoxycinnamic acid was first documented in 2001 (PMID: 11368919). Based on a literature review a significant number of articles have been published on Isoferulic acid (PMID: 14690369) (PMID: 15693705) (PMID: 14756917) (PMID: 12906912) (PMID: 15971118) (PMID: 34208366).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0331730 (3-Hydroxy-4-methoxycinnamic acid)


  Mrv1652309272007392D          

 14 14  0  0  0  0            999 V2000
10000.732310000.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4470 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.161810000.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8766 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.161810001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.878910000.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8789 9998.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.021110000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.306610000.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592110000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5921 9999.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3065 9998.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0211 9999.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1644 9999.1765    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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  1  8  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
  7 14  1  0  0  0  0
M  END
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3D MOL for NP0331730 (3-Hydroxy-4-methoxycinnamic acid)

HMDB0000955
     RDKit          3D
Isoferulic acid
 24 24  0  0  0  0  0  0  0  0999 V2000
   -4.2839    1.1524   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3849    0.2770   -0.8237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511    0.1222   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4931    0.9454    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711    0.8609    0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -0.0473    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0904   -0.0913    0.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9659   -0.9153    0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3710   -0.9238    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1677   -1.7131   -0.0377 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7516   -0.0388    1.4414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -0.8654   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -0.7690   -1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7629   -1.5992   -2.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1443    1.3165   -0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7926    2.1565   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6286    0.9222    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492    1.6797    0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378    1.5049    1.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    0.5859    1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6409   -1.6071   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962    0.9038    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536   -1.5890   -1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594   -2.2681   -2.5687 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 14  1  0
 13  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
Download

3D SDF for NP0331730 (3-Hydroxy-4-methoxycinnamic acid)


  Mrv1652309272007392D          

 14 14  0  0  0  0            999 V2000
10000.732310000.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4470 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.161810000.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8766 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.161810001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.878910000.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8789 9998.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.021110000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.306610000.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592110000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5921 9999.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3065 9998.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0211 9999.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1644 9999.1765    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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  1  8  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
  7 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331730

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

> <INCHI_KEY>
QURCVMIEKCOAJU-HWKANZROSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.36264757677008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
1.6748496726666668

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.852538782041124

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.767472407589629

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889780749263311

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
51.50400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoferulic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0331730 (3-Hydroxy-4-methoxycinnamic acid)

HMDB0000955
     RDKit          3D
Isoferulic acid
 24 24  0  0  0  0  0  0  0  0999 V2000
   -4.2839    1.1524   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3849    0.2770   -0.8237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511    0.1222   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4931    0.9454    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711    0.8609    0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -0.0473    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0904   -0.0913    0.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9659   -0.9153    0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3710   -0.9238    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1677   -1.7131   -0.0377 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7516   -0.0388    1.4414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -0.8654   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -0.7690   -1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7629   -1.5992   -2.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1443    1.3165   -0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7926    2.1565   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6286    0.9222    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492    1.6797    0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378    1.5049    1.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    0.5859    1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6409   -1.6071   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962    0.9038    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536   -1.5890   -1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594   -2.2681   -2.5687 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 14  1  0
 13  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
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PDB for NP0331730 (3-Hydroxy-4-methoxycinnamic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.0348667.435   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3688666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.7028667.435   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8672.0368666.666   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8670.7028668.974   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.7078667.435   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8662.7078664.359   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8666.7068666.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.3728667.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.0398666.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0398665.128   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3728664.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.7068665.128   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.3748665.129   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6   10                                                            
CONECT    7   11   14                                                       
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    6                                                  
CONECT   11   10   12    7                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    7                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for NP0331730 (3-Hydroxy-4-methoxycinnamic acid)

COMPND    HMDB0000955
HETATM    1  C1  UNL     1      -4.284   1.152  -0.266  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.385   0.277  -0.824  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.051   0.122  -0.551  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.493   0.945   0.416  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.171   0.861   0.752  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.691  -0.047   0.151  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.090  -0.091   0.551  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.966  -0.915   0.035  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.371  -0.924   0.470  1.00  0.00           C  
HETATM   10  O2  UNL     1       5.168  -1.713  -0.038  1.00  0.00           O  
HETATM   11  O3  UNL     1       4.752  -0.039   1.441  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.134  -0.865  -0.811  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.221  -0.769  -1.146  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.763  -1.599  -2.116  1.00  0.00           O  
HETATM   15  H1  UNL     1      -5.144   1.317  -0.975  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.793   2.156  -0.195  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.629   0.922   0.753  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.149   1.680   0.915  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.238   1.505   1.501  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.442   0.586   1.313  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.641  -1.607  -0.734  1.00  0.00           H  
HETATM   22  H8  UNL     1       4.996   0.904   1.149  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.754  -1.589  -1.312  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.159  -2.268  -2.569  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   12
CONECT    7    8    8   20
CONECT    8    9   21
CONECT    9   10   10   11
CONECT   11   22
CONECT   12   13   13   23
CONECT   13   14
CONECT   14   24
END
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SMILES for NP0331730 (3-Hydroxy-4-methoxycinnamic acid)

COC1=C(O)C=C(\C=C\C(O)=O)C=C1
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INCHI for NP0331730 (3-Hydroxy-4-methoxycinnamic acid)

InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
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View in JSmol
Synonyms
ValueSource
3-Hydroxy-4-methoxycinnamic acidChEBI
Hesperetic acidChEBI
3-Hydroxy-4-methoxycinnamateGenerator
HesperetateGenerator
IsoferulateGenerator
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoateHMDB
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acidHMDB
3-Hydroxy-4-methoxy-cinnamateHMDB
3-Hydroxy-4-methoxy-cinnamic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acidHMDB
(e)-3-Hydroxy-4-methoxycinnamic acidHMDB
(e)-4-Methoxycaffeic acidHMDB
(e)-4-O-Methylcaffeic acidHMDB
(e)-Hesperetic acidHMDB
(e)-Isoferulic acidHMDB
4-Methoxycaffeic acidHMDB
4-O-Methylcaffeic acidHMDB
trans-3-Hydroxy-4-methoxycinnamic acidHMDB
trans-4-Methoxycaffeic acidHMDB
trans-4-O-Methylcaffeic acidHMDB
trans-Hesperetic acidHMDB
trans-Isoferulic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoateHMDB
3'-Hydroxy-4'-methoxycinnamic acidHMDB
(e)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidHMDB
Isoferulic acidHMDB
3-(3-Hydroxy-4-methoxyphenyl)acrylic acidHMDB
Chemical FormulaC10H10O4
Average Mass194.1840 Da
Monoisotopic Mass194.05791 Da
IUPAC Name(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
Traditional Nameisoferulic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C(\C=C\C(O)=O)C=C1
InChI Identifier
InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChI KeyQURCVMIEKCOAJU-HWKANZROSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-14View Spectrum
Species
Species of OriginNot Available
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
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • 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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.56ALOGPS
logP1.67ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.5 m³·mol⁻¹ChemAxon
Polarizability19.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000955
DrugBank IDDB07109
Phenol Explorer Compound ID485
FoodDB IDFDB002700
KNApSAcK IDC00002752
Chemspider ID643318
KEGG Compound IDC10470
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoferulic acid
METLIN ID5901
PubChem Compound736186
PDB IDNot Available
ChEBI ID27794
Good Scents IDrw1190521
References
General References
  1. Kern SM, Bennett RN, Needs PW, Mellon FA, Kroon PA, Garcia-Conesa MT: Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells. J Agric Food Chem. 2003 Dec 31;51(27):7884-91. [PubMed:14690369 ]
  2. Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38. [PubMed:15693705 ]
  3. Rechner AR, Spencer JP, Kuhnle G, Hahn U, Rice-Evans CA: Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free Radic Biol Med. 2001 Jun 1;30(11):1213-22. [PubMed:11368919 ]
  4. Hodgson JM, Chan SY, Puddey IB, Devine A, Wattanapenpaiboon N, Wahlqvist ML, Lukito W, Burke V, Ward NC, Prince RL, Croft KD: Phenolic acid metabolites as biomarkers for tea- and coffee-derived polyphenol exposure in human subjects. Br J Nutr. 2004 Feb;91(2):301-6. [PubMed:14756917 ]
  5. Wittemer SM, Veit M: Validated method for the determination of six metabolites derived from artichoke leaf extract in human plasma by high-performance liquid chromatography-coulometric-array detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Aug 15;793(2):367-75. [PubMed:12906912 ]
  6. Stromeier S, Petereit F, Nahrstedt A: Phenolic esters from the rhizomes of Cimicifuga racemosa do not cause proliferation effects in MCF-7 cells. Planta Med. 2005 Jun;71(6):495-500. [PubMed:15971118 ]
  7. Kalinowska M, Golebiewska E, Mazur L, Lewandowska H, Pruszynski M, Swiderski G, Wyrwas M, Pawluczuk N, Lewandowski W: Crystal Structure, Spectroscopic Characterization, Antioxidant and Cytotoxic Activity of New Mg(II) and Mn(II)/Na(I) Complexes of Isoferulic Acid. Materials (Basel). 2021 Jun 11;14(12). pii: ma14123236. doi: 10.3390/ma14123236. [PubMed:34208366 ]
  8. Hori K, Watanabe T, Devkota HP: Phenolic Acid Derivatives, Flavonoids and Other Bioactive Compounds from the Leaves of Cardiocrinum cordatum (Thunb.) Makino (Liliaceae). Plants (Basel). 2021 Feb 7;10(2). pii: plants10020320. doi: 10.3390/plants10020320. [PubMed:33562289 ]
  9. Jiang X, Tao L, Li C, You M, Li GQ, Zhang C, Hu F: Grouping, Spectrum-Effect Relationship and Antioxidant Compounds of Chinese Propolis from Different Regions Using Multivariate Analyses and Off-Line Anti-DPPH Assay. Molecules. 2020 Jul 16;25(14). pii: molecules25143243. doi: 10.3390/molecules25143243. [PubMed:32708723 ]
  10. Serreli G, Naitza MR, Zodio S, Leoni VP, Spada M, Melis MP, Boronat A, Deiana M: Ferulic Acid Metabolites Attenuate LPS-Induced Inflammatory Response in Enterocyte-like Cells. Nutrients. 2021 Sep 10;13(9):3152. doi: 10.3390/nu13093152. [PubMed:34579029 ]
  11. Serreli G, Le Sayec M, Thou E, Lacour C, Diotallevi C, Dhunna MA, Deiana M, Spencer JPE, Corona G: Ferulic Acid Derivatives and Avenanthramides Modulate Endothelial Function through Maintenance of Nitric Oxide Balance in HUVEC Cells. Nutrients. 2021 Jun 12;13(6):2026. doi: 10.3390/nu13062026. [PubMed:34204635 ]
  12. Kim MA, Lee HJ, Bae HG, Yang SO, Lee HJ, Kim MJ: Metabolite analysis and anti-obesity effects of celery seed in 3T3-L1 adipocytes. Food Sci Biotechnol. 2021 Feb 23;30(2):277-286. doi: 10.1007/s10068-020-00866-9. eCollection 2021 Feb. [PubMed:33732518 ]
  13. Huang JY, Zhang Q, Yang YL, Yang HJ, Dou MH, Li HH, DU SY, Bai J: [Analysis on quality value transfer of substance benchmarks of Qingwei San]. Zhongguo Zhong Yao Za Zhi. 2021 Feb;46(4):792-800. doi: 10.19540/j.cnki.cjcmm.20201102.301. [PubMed:33645083 ]
  14. Agullo V, Garcia-Viguera C, Dominguez-Perles R: Beverages Based on Second Quality Citrus Fruits and Maqui Berry, a Source of Bioactive (Poly)phenols: Sorting Out Urine Metabolites upon a Longitudinal Study. Nutrients. 2021 Jan 22;13(2):312. doi: 10.3390/nu13020312. [PubMed:33499139 ]
  15. Zhang Q, Huang JY, Zhong WL, Liu LL, Zhang YM, Yang LJ, Bai J, DU SY: [Characteristic spectrum and decoction process of classical prescription Qingwei San]. Zhongguo Zhong Yao Za Zhi. 2020 Dec;45(23):5607-5613. doi: 10.19540/j.cnki.cjcmm.20200706.307. [PubMed:33496098 ]
  16. Wohl J, Petersen M: Phenolic metabolism in the hornwort Anthoceros agrestis: 4-coumarate CoA ligase and 4-hydroxybenzoate CoA ligase. Plant Cell Rep. 2020 Sep;39(9):1129-1141. doi: 10.1007/s00299-020-02552-w. Epub 2020 May 13. [PubMed:32405654 ]
  17. Wu Y, Xu Y, Yang A, Shen S, Mi D, Cao Y, Hua Z, Min L, Li W: Comparative in vivo pharmacokinetics study of affeic acid, isoferulic acid and ferulic acid in crude and three different prepared Cimicifuga foetida L. Biomed Chromatogr. 2020 Sep;34(9):e4868. doi: 10.1002/bmc.4868. Epub 2020 Jul 4. [PubMed:32335934 ]
  18. Olech M, Pietrzak W, Nowak R: Characterization of Free and Bound Phenolic Acids and Flavonoid Aglycones in Rosa rugosa Thunb. Leaves and Achenes Using LC-ESI-MS/MS-MRM Methods. Molecules. 2020 Apr 15;25(8):1804. doi: 10.3390/molecules25081804. [PubMed:32326454 ]
  19. Jiang L, Xie M, Chen G, Qiao J, Zhang H, Zeng X: Phenolics and Carbohydrates in Buckwheat Honey Regulate the Human Intestinal Microbiota. Evid Based Complement Alternat Med. 2020 Feb 26;2020:6432942. doi: 10.1155/2020/6432942. eCollection 2020. [PubMed:32184894 ]
  20. Martinez MD, Riva DA, Garcia C, Duran FJ, Burton G: Synthesis and Antibacterial Activity of Difluoromethyl Cinnamoyl Amides. Molecules. 2020 Feb 12;25(4):789. doi: 10.3390/molecules25040789. [PubMed:32059479 ]
  21. Agullo V, Villano D, Garcia-Viguera C, Dominguez-Perles R: Anthocyanin Metabolites in Human Urine after the Intake of New Functional Beverages. Molecules. 2020 Jan 16;25(2):371. doi: 10.3390/molecules25020371. [PubMed:31963236 ]
  22. Moreira SA, Silva S, Costa EM, Saraiva JA, Pintado M: Effect of high hydrostatic pressure extraction on biological activities of stinging nettle extracts. Food Funct. 2020 Jan 29;11(1):921-931. doi: 10.1039/c9fo02442e. [PubMed:31950959 ]
  23. Long Z, Feng G, Zhao N, Wu L, Zhu H: Isoferulic acid inhibits human leukemia cell growth through induction of G2/M‑phase arrest and inhibition of Akt/mTOR signaling. Mol Med Rep. 2020 Mar;21(3):1035-1042. doi: 10.3892/mmr.2020.10926. Epub 2020 Jan 9. [PubMed:31922221 ]
  24. Oniszczuk A, Widelska G, Wojtowicz A, Oniszczuk T, Wojtunik-Kulesza K, Dib A, Matwijczuk A: Content of Phenolic Compounds and Antioxidant Activity of New Gluten-Free Pasta with the Addition of Chestnut Flour. Molecules. 2019 Jul 18;24(14):2623. doi: 10.3390/molecules24142623. [PubMed:31323897 ]
  25. Shen S, Wang J, Chen X, Liu T, Zhuo Q, Zhang SQ: Evaluation of cellular antioxidant components of honeys using UPLC-MS/MS and HPLC-FLD based on the quantitative composition-activity relationship. Food Chem. 2019 Sep 30;293:169-177. doi: 10.1016/j.foodchem.2019.04.105. Epub 2019 Apr 26. [PubMed:31151598 ]
  26. Si D, Sun X, Qi D, Chen X, Bi K: Determination and pharmacokinetics of isoferulic acid in rat plasma by high-performance liquid chromatography after oral administration of isoferulic acid and Rhizoma Cimicifugae extract. J Pharm Biomed Anal. 2008 May 12;47(1):140-5. doi: 10.1016/j.jpba.2007.12.044. Epub 2008 Jan 18. [PubMed:18314290 ]
  27. Farrell TL, Dew TP, Poquet L, Hanson P, Williamson G: Absorption and metabolism of chlorogenic acids in cultured gastric epithelial monolayers. Drug Metab Dispos. 2011 Dec;39(12):2338-46. doi: 10.1124/dmd.111.040147. Epub 2011 Sep 21. [PubMed:21937734 ]
  28. Wang X, Li X, Chen D: Evaluation of antioxidant activity of isoferulic acid in vitro. Nat Prod Commun. 2011 Sep;6(9):1285-8. [PubMed:21941899 ]