Hmdb loader

Showing metabocard for Isoferulic acid (HMDB0000955)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:20 UTC
HMDB IDHMDB0000955
Secondary Accession Numbers
  • HMDB00955
Metabolite Identification
Common NameIsoferulic acid
DescriptionIsoferulic acid (CAS: 537-73-5) is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids (e.g. caffeic acid, ferulic acid, and p-coumaric acid) with quinic acid. CGAs are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2-9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation (PMID:17884997 ).
Structure
Data?1676999720
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000955 (Isoferulic 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 HMDB0000955 (Isoferulic 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 HMDB0000955 (Isoferulic 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>
HMDB0000955

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0000955 (Isoferulic 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 HMDB0000955 (Isoferulic 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 HMDB0000955 (Isoferulic 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 HMDB0000955 (Isoferulic acid)

COC1=C(O)C=C(\C=C\C(O)=O)C=C1
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INCHI for HMDB0000955 (Isoferulic 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 JSmolView Stereo Labels
Synonyms
ValueSource
3-Hydroxy-4-methoxycinnamic acidChEBI
Hesperetic acidChEBI
3-Hydroxy-4-methoxycinnamateGenerator
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
Chemical FormulaC10H10O4
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
IUPAC Name(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
Traditional Nameisoferulic acid
CAS Registry Number25522-33-2
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 - 233 °CNot Available
Boiling Point409.00 to 411.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility7191 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.788 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.87 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+142.11632859911
AllCCS[M-H]-141.26232859911
DeepCCS[M+H]+147.21730932474
DeepCCS[M-H]-144.85930932474
DeepCCS[M-2H]-178.47930932474
DeepCCS[M+Na]+153.40630932474
AllCCS[M+H]+142.132859911
AllCCS[M+H-H2O]+137.932859911
AllCCS[M+NH4]+146.032859911
AllCCS[M+Na]+147.132859911
AllCCS[M-H]-141.332859911
AllCCS[M+Na-2H]-141.832859911
AllCCS[M+HCOO]-142.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isoferulic acidCOC1=C(O)C=C(\C=C\C(O)=O)C=C13520.8Standard polar33892256
Isoferulic acidCOC1=C(O)C=C(\C=C\C(O)=O)C=C11851.2Standard non polar33892256
Isoferulic acidCOC1=C(O)C=C(\C=C\C(O)=O)C=C11938.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoferulic acid,1TMS,isomer #1COC1=CC=C(/C=C/C(=O)O)C=C1O[Si](C)(C)C2026.7Semi standard non polar33892256
Isoferulic acid,1TMS,isomer #2COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C)C=C1O2046.3Semi standard non polar33892256
Isoferulic acid,2TMS,isomer #1COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C2081.6Semi standard non polar33892256
Isoferulic acid,1TBDMS,isomer #1COC1=CC=C(/C=C/C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2319.5Semi standard non polar33892256
Isoferulic acid,1TBDMS,isomer #2COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)C=C1O2311.5Semi standard non polar33892256
Isoferulic acid,2TBDMS,isomer #1COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2605.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-0900000000-b51b390a0727d3838cab2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7094000000-6021a908fd1b4eec8f002017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoferulic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-db5f99d89dd9e349c86c2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-004l-0900000000-ab3320c9d0dfcba00b6e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-001i-0900000000-2b9775043a4af5fdc0642012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-001i-0900000000-29fd32eacfaa527045592012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0006-0900000000-d26e8f9f43c25710a04d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-003r-0900000000-25d10f2b53d4679375242012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-001i-0900000000-b2f1dd5274585c5f6b0b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-001i-3900000000-2e21dbcbb598dba645252012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-001i-2900000000-7a28000b74f8c4f5b27f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 40V, Negative-QTOFsplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 10V, Negative-QTOFsplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 30V, Negative-QTOFsplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 50V, Negative-QTOFsplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF , Negative-QTOFsplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 20V, Negative-QTOFsplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 40V, Negative-QTOFsplash10-001i-0900000000-623ecba5385a03e0406b2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0900000000-205ebeb435685d894bcf2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 30V, Negative-QTOFsplash10-001i-0900000000-97eb2cfc1a86c4933f762017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF 50V, Negative-QTOFsplash10-001i-0900000000-49f1d1fd82311df297132017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoferulic acid ESI-TOF , Negative-QTOFsplash10-005l-0902100000-6fc8730bd28daa779b662017-09-12HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoferulic acid 10V, Positive-QTOFsplash10-002b-0900000000-eaa8fbddbddb5c585ea42017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoferulic acid 20V, Positive-QTOFsplash10-002b-1900000000-c2fa54dcd41f9ab16b8e2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoferulic acid 40V, Positive-QTOFsplash10-00fs-5900000000-a969ea13d0a4ad63b2a62017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoferulic acid 10V, Negative-QTOFsplash10-0006-0900000000-6b2f8b891907a56146d62017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoferulic acid 20V, Negative-QTOFsplash10-0006-0900000000-6139186c0691cc7b95bb2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoferulic acid 40V, Negative-QTOFsplash10-00o0-2900000000-8d4f500b0c438df01f412017-06-28Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.128 +/- 0.018 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.126 +/- 0.028 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.169 +/- 0.03 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.187 +/- 0.048 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.105 +/- 0.021 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.083 +/- 0.01 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.118 +/- 0.016 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified1.549 +/- 1.451 uMAdult (>18 years old)Male
Normal		 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected and Quantified18.591 +/- 1.0814 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified21.835 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified21.989 +/- 5.304 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0402 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0572 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
UrineDetected and Quantified0.394 +/- 0.075 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07109
Phenol Explorer Compound ID485
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1190521
References
Synthesis ReferenceMauthner, P. New synthesis of isoferulic acid. Journal fuer Praktische Chemie (Leipzig) (1922), 104 132-6.
Material Safety Data Sheet (MSDS)Download (PDF)
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. Monteiro M, Farah A, Perrone D, Trugo LC, Donangelo C: Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J Nutr. 2007 Oct;137(10):2196-201. [PubMed:17884997 ]