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Showing NP-Card for Isoferulic acid (NP0001157)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:16:01 UTC
NP-MRD IDNP0001157
Natural Product DOIhttps://doi.org/10.57994/0493
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001157 (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
Download

3D MOL for NP0001157 (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 NP0001157 (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>
NP0001157

> <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

$$$$
Download

3D-SDF for NP0001157 (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

PDB for NP0001157 (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 NP0001157 (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 NP0001157 (Isoferulic acid)

COC1=C(O)C=C(\C=C\C(O)=O)C=C1
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INCHI for NP0001157 (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 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 Number537-73-5
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)jtkp6n@mail.missouri.eduNot AvailableNot Available2023-02-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)jtkp6n@mail.missouri.eduNot AvailableNot Available2023-02-25View 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
Not Available
Species
Species of Origin
Species NameSourceReference
Abies firmaLOTUS Database
Actaea cimicifugaLOTUS Database
Actaea dahuricaLOTUS Database
Actaea heracleifoliaLOTUS Database
Actaea japonicaLOTUS Database
Actaea racemosaKNApSAcK Database
Actaea simplexLOTUS Database
Angelica pubescensLOTUS Database
Arachis hypogaeaFooDB
Artemisia capillarisLOTUS Database
Artemisia minorKNApSAcK Database
Astragalus onobrychisLOTUS Database
Blainvillea acmellaLOTUS Database
Bromelia pinguinLOTUS Database
Calligonum leucocladumKNApSAcK Database
Catalpa ovataKNApSAcK Database
Chondrilla junceaLOTUS Database
Chrysanthemum coronariumLOTUS Database
Cimicifuga racemosaKNApSAcK Database
Cynanchum thesioidesLOTUS Database
Cyperus conglomeratusLOTUS Database
Digitalis ferrugineaLOTUS Database
Ephedra sinicaKNApSAcK Database
Glycine maxFooDB
Halocharis hispidaLOTUS Database
Helianthus annuus L.FooDB
Hyssopus officinalis L.LOTUS Database
Imperata cylindricaLOTUS Database
Lemna aequinoctialisLOTUS Database
Lycopus europaeusLOTUS Database
Marrubium cylleneumLOTUS Database
Matricaria recutitaFooDB
Populus cathayanaLOTUS Database
Populus euphraticaLOTUS Database
Populus simoniiLOTUS Database
Potentilla erectaLOTUS Database
Salvia miltiorrhizaKNApSAcK Database
Sarcandra glabraKNApSAcK Database
Sibiraea angustataLOTUS Database
Tamarix aphyllaKNApSAcK Database
Tamarix niloticaLOTUS Database
Triticum aestivumFooDB
Urospermum picroidesLOTUS Database
Vaccinium myrtillusFooDB
Valeriana officinalisLOTUS Database
Viola arvensisLOTUS Database
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
StateSolid
Experimental 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
Predicted 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
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 ]