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Showing NP-Card for Ferulic acid (NP0003003)

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Record Information
Version2.0
Created at2020-11-23 19:46:31 UTC
Updated at2024-09-03 04:16:43 UTC
NP-MRD IDNP0003003
Natural Product DOIhttps://doi.org/10.57994/0774
Secondary Accession NumbersNone
Natural Product Identification
Common NameFerulic acid
Provided ByBMRBBMRB logo
DescriptionFerulic acid, also known as (e)-ferulate or trans-ferulate, 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. Ferulic acid exists in all living species, ranging from bacteria to plants to humans. Ferulic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Ferulic acid is found in Abeliophyllum distichum, Abies nephrolepis, Abies spectabilis, Actaea japonica, Actaea racemosa, Actaea simplex, Adenostoma sparsifolium, Ailanthus integrifolia, Aloe castellorum, Ammodendron bifolium, Anastatica hierochuntica, Andrographis paniculata, Anemone cernua, Angelica dahurica, Angelica sinensis, Anigozanthos preissii, Aristolochia elegans, Aristolochia kaempferi, Artemisia capillaris, Aruncus dioicus, Aspergillus unilateralis, Aster indicus, Astragalus onobrychis, Avena sativa, Blainvillea acmella, Broussonetia papyrifera, Buddleja asiatica, Calycanthus chinensis, Camellia reticulata, Campanula rotundifolia, Caragana spinosa, Centaurea africana, Chaerophyllum hirsutum, Chamaecyparis formosensis, Cinnamomum kotoense, Cinnamomum subavenium, Cinnamomum tenuifolium, Citrus medica, Citrus sinensis, Clematis terniflora, Coriandrum sativum, Cryptomeria japonica, Equisetum ramosissimum, Equisetum telmateia, Eriocaulon buergerianum, Euphorbia tithymaloides, Euphrasia officinalis, Ferula foetida, Glechoma hederacea, Glehnia littoralis, Gymnadenia conopsea, Gymnanthemum myrianthum, Gynerium sagittatum, Halimodendron halodendron, Haplopteris anguste-elongata, Hedychium coronarium, Helichrysum italicum, Heracleum sphondylium, Hibiscus taiwanensis, Hornstedtia reticulata, Hylocereus undatus, Hypericum laricifolium, Impatiens balsamina, Ipomoea nil, Iris ensata, Isodon japonicus, Kalanchoe pinnata, Kigelia africana, Larix sibirica, Ligularia nelumbifolia, Ligularia veitchiana, Ligusticum multivittatum, Ligusticum porteri, Lithospermum erythrorhizon, Macaranga triloba, Mallotus metcalfianus, Malus domestica, Marrubium cylleneum, Matricaria chamomilla, Magnolia compressa, Murraya paniculata, Hansenia forbesii, Oenanthe javanica, Opuntia ficus-indica, Peperomia heyneana, Petasites formosanus, Petunia axillaris, Phedimus kamtschaticus, Phellodendron amurense, Phellodendron chinense, Phragmites australis, Picea glauca, Picea neoveitchii, Plantago major, Populus tremuloides, Posidonia oceanica, Prunus africana, Pterogyne nitens, Quercus ilex, Ranunculus sieboldii, Reseda muricata, Rhodiola heterodonta, Rorippa indica, Sabia japonica, Salvia fruticosa, Sargentodoxa cuneata, Scrophularia buergeriana, Scutellaria albida, Silphium perfoliatum, Sophora alopecuroides, Sparganium stoloniferum, Tamarix aphylla, Taraxacum mongolicum, Triticum turgidum, Valeriana laxiflora, Verbesina gigantea, Viburnum dilatatum, Viscum album, Viscum coloratum, Vitex agnus-castus, Vitis vinifera, Xanthium strumarium, Xanthorhiza simplicissima, Zea mays and Ziziphora clinopodioides. Ferulic acid was first documented in 2021 (PMID: 34600676). Based on a literature review a small amount of articles have been published on Ferulic acid (PMID: 34597652) (PMID: 34595237) (PMID: 34580932).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0003003 (Ferulic acid)


  Mrv1652309272007352D          

 14 14  0  0  0  0            999 V2000
10000.732310000.4119    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
10002.161810000.4119    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
 9997.878910000.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1633 9999.9989    0.0000 C   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
10000.021210000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.306710000.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592210000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5922 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3066 9998.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0212 9999.1758    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
  6  7  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  1  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
Download

3D MOL for NP0003003 (Ferulic acid)

HMDB0000954
     RDKit          3D
Ferulic acid
 24 24  0  0  0  0  0  0  0  0999 V2000
   -3.0115    2.2634    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1116    0.9211   -0.2517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890    0.0809   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7503    0.5772    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068   -0.2078   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    0.4076    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -0.2739    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505    0.3100    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0924    1.5036    1.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976   -0.4310    0.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2249   -1.5045   -0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163   -2.0188   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356   -1.2338   -0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4049   -1.6994   -1.0339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5716    2.8884   -0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4290    2.4181    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    2.6293    0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970    1.6273    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6904    1.4559    0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032   -1.3255    0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8458   -0.5492    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -2.1497   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1062   -3.0430   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619   -2.6462   -1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  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
  6 19  1  0
  7 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
Download

3D SDF for NP0003003 (Ferulic acid)


  Mrv1652309272007352D          

 14 14  0  0  0  0            999 V2000
10000.732310000.4119    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
10002.161810000.4119    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
 9997.878910000.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1633 9999.9989    0.0000 C   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
10000.021210000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.306710000.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592210000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5922 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3066 9998.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0212 9999.1758    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
  6  7  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  1  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003003

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
KSEBMYQBYZTDHS-HWKANZROSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.180103670792548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.6748496726666668

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.982312921511172

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7673485922827705

> <JCHEM_PKA_STRONGEST_BASIC>
-4.89396153310966

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
51.504000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ferulic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0003003 (Ferulic acid)

HMDB0000954
     RDKit          3D
Ferulic acid
 24 24  0  0  0  0  0  0  0  0999 V2000
   -3.0115    2.2634    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1116    0.9211   -0.2517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890    0.0809   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7503    0.5772    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068   -0.2078   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    0.4076    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -0.2739    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505    0.3100    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0924    1.5036    1.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976   -0.4310    0.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2249   -1.5045   -0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163   -2.0188   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356   -1.2338   -0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4049   -1.6994   -1.0339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5716    2.8884   -0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4290    2.4181    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    2.6293    0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970    1.6273    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6904    1.4559    0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032   -1.3255    0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8458   -0.5492    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -2.1497   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1062   -3.0430   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619   -2.6462   -1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  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
  6 19  1  0
  7 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
M  END
Download

PDB for NP0003003 (Ferulic 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    8668.0348667.436   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    8670.7028667.436   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    8662.7078667.436   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8661.3718666.665   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8662.7078664.359   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8666.7068666.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3738667.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0398666.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0398665.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3728664.358   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.7068665.128   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   11                                                       
CONECT    7    6                                                            
CONECT    8   12                                                            
CONECT    9   10   14    1                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12    6                                                  
CONECT   12   11   13    8                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
Download

3D PDB for NP0003003 (Ferulic acid)

COMPND    HMDB0000954
HETATM    1  C1  UNL     1      -3.011   2.263   0.141  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.112   0.921  -0.252  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.989   0.081  -0.315  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.750   0.577   0.016  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.407  -0.208  -0.026  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.646   0.408   0.338  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.775  -0.274   0.321  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.050   0.310   0.682  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.092   1.504   1.024  1.00  0.00           O  
HETATM   10  O3  UNL     1       5.198  -0.431   0.651  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.225  -1.504  -0.419  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.016  -2.019  -0.755  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.136  -1.234  -0.707  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.405  -1.699  -1.034  1.00  0.00           O  
HETATM   15  H1  UNL     1      -2.572   2.888  -0.664  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.429   2.418   1.066  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.047   2.629   0.374  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.697   1.627   0.320  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.690   1.456   0.640  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.803  -1.325   0.029  1.00  0.00           H  
HETATM   21  H7  UNL     1       5.846  -0.549   1.417  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.099  -2.150  -0.465  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.106  -3.043  -1.057  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.562  -2.646  -1.324  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   11   11
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9    9   10
CONECT   10   21
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14
CONECT   14   24
END
Download

SMILES for NP0003003 (Ferulic acid)

COC1=C(O)C=CC(\C=C\C(O)=O)=C1
Download

INCHI for NP0003003 (Ferulic acid)

InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(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
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidChEBI
(e)-4'-Hydroxy-3'-methoxycinnamic acidChEBI
(e)-4-Hydroxy-3-methoxycinnamic acidChEBI
(e)-Ferulic acidChEBI
3-(4-Hydroxy-3-methoxyphenyl)propenoic acidChEBI
3-Methoxy-4-hydroxy-trans-cinnamic acidChEBI
4-Hydroxy-3-methoxycinnamic acidChEBI
trans-4-Hydroxy-3-methoxycinnamic acidChEBI
trans-Ferulic acidChEBI
3-Methoxy-4-hydroxy-trans-cinnamateKegg
4-Hydroxy-3-methoxycinnamateKegg
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoateGenerator
(e)-4'-Hydroxy-3'-methoxycinnamateGenerator
(e)-4-Hydroxy-3-methoxycinnamateGenerator
(e)-FerulateGenerator
3-(4-Hydroxy-3-methoxyphenyl)propenoateGenerator
trans-4-Hydroxy-3-methoxycinnamateGenerator
trans-FerulateGenerator
FerulateGenerator
8,8'-Diferulic acidHMDB
Ferulic acid, (e)-isomerHMDB
Ferulic acid, monosodium saltHMDB
Sodium ferulateHMDB
Ferulic acid, (Z)-isomerHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoateHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidHMDB
(e)-4-Hydroxy-3-methoxy-cinnamateHMDB
(e)-4-Hydroxy-3-methoxy-cinnamic acidHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acidHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acidHMDB
(e)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acidHMDB
Fumalic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidHMDB
3-Methoxy-4-hydroxycinnamic acidHMDB
4'-Hydroxy-3'-methoxycinnamic acidHMDB
Coniferic acidHMDB
Ferulaic acidHMDB
4’-hydroxy-3’-methoxycinnamic acidHMDB
Ferulic acidHMDB, KEGG
3-(4-Hydroxy-3-methoxyphenyl)acrylic acidHMDB
cis-Ferulic acidMeSH
Chemical FormulaC10H10O4
Average Mass194.1840 Da
Monoisotopic Mass194.05791 Da
IUPAC Name(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Traditional Nameferulic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(\C=C\C(O)=O)=C1
InChI Identifier
InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChI KeyKSEBMYQBYZTDHS-HWKANZROSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-26View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 600 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
Abeliophyllum distichum
Abelmoschus esculentus
Abies nephrolepis
Abies spectabilis
Actaea japonica
Actaea racemosa
Actaea simplex
Actinidia chinensis
Adenostoma sparsifolium
Agaricus bisporus
Agave
Ailanthus integrifolia
Allium ampeloprasumFooDB
Allium ascalonicum
Allium cepaFooDB
Allium cepa L.
Allium fistulosum
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosum
Aloe castellorum
Aloysia triphylla
Amaranthus
Amelanchier alnifolia
Ammodendron bifolium
Anacardium occidentale
Ananas comosusFooDB
Anastatica hierochuntica
Andrographis paniculata
Anemone cernua
Anethum graveolensFooDB
Angelica dahurica
Angelica keiskei
Angelica sinensis
Anigozanthos preissii
Annona cherimola
Annona muricata
Annona reticulata
Annona squamosa
Anthriscus cerefolium
Apium graveolensFooDB
Apium graveolens var. dulce
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Arachis hypogaeaFooDB
Arctium lappa
Aristolochia elegans
Aristolochia kaempferi
Armoracia rusticana
Artemisia capillaris
Artemisia dracunculusFooDB
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllus
Aruncus dioicus
Asparagus officinalis
Aspergillus unilateralis
Aster indicus
Astragalus onobrychis
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa
Avena sativa L.FooDB
Averrhoa carambola
Basella albaFooDB
Benincasa hispida
Bertholletia excelsa
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Blainvillea acmella
Borago officinalis
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napusFooDB
Brassica oleracea
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodes
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabauda
Brassica oleracea var. viridis
Brassica rapa
Brassica rapa ssp. chinensis
Brassica rapa var. pekinensis
Brassica rapa var. rapaFooDB
Brassica ruvo
Brosimum alicastrum
Broussonetia papyrifera
Buddleja asiatica
Byrsonima crassifolia
Cajanus cajanFooDB
Calycanthus chinensis
Camellia reticulata
Campanula rotundifolia
Canarium ovatum
Cantharellus cibarius
Capparis spinosa
Capsicum annuumFooDB
Capsicum annuum L.
Capsicum annuum var. annuumFooDB
Capsicum chinense
Capsicum pubescens
Caragana spinosa
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carvi
Carya
Carya illinoinensis
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Centaurea africana
Ceratonia siliquaFooDB
Chaerophyllum hirsutum
Chamaecyparis formosensis
Chamaemelum nobileFooDB
Chamerion angustifolium
Chenopodium albumFooDB
Chenopodium quinoa
Chrysanthemum coronarium
Cicer arietinumFooDB
Cichorium endivia
Cichorium intybusFooDB
Cinnamomum
Cinnamomum aromaticum
Cinnamomum kotoense
Cinnamomum subavenium
Cinnamomum tenuifolium
Cinnamomum verum
Cirsium
Citrullus lanatus
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifolia
Citrus latifolia
Citrus limonFooDB
Citrus maxima
Citrus medica
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus sinensis
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clematis terniflora
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculenta
Corchorus olitorius
Coriandrum sativum
Coriandrum sativum L.FooDB
Corylus
Corylus avellana
Crateva religiosa
Crocus sativus
Cryptomeria japonica
Cucumis meloFooDB
Cucumis metuliferus
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maxima
Cucurbita moschata
Cuminum cyminumFooDB
Curcuma longa
Cydonia oblongaFooDB
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • Adrian J. Parr, Annie Ng, and Keith W. Waldron Ester-Linked Phenolic Components of Carrot Cell Wa...
Dimocarpus longan
Dioscorea
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Durio zibethinus
Dysphania ambrosioides
Elaeis
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
Equisetum ramosissimum
Equisetum telmateia
Eragrostis tef
Eriobotrya japonica
Eriocaulon buergerianum
Eruca vesicaria subsp. Sativa
Eugenia javanica
Eugenia uniflora
Euphorbia tithymaloides
Euphrasia officinalis
Eutrema japonicum
Fagopyrum esculentumFooDB
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ferula foetida
Ficus caricaFooDB
Flammulina velutipes
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Garcinia mangostana
Gaylussacia baccataFooDB
Ginkgo biloba
Glechoma hederacea
Glehnia littoralis
Glycine maxFooDB
Gossypium
Grifola frondosa
Gymnadenia conopsea
Gymnanthemum myrianthum
Gynerium sagittatum
Halimodendron halodendron
Haplopteris anguste-elongata
Hedychium coronarium
Hedysarum alpinum
Helianthus annuus L.FooDB
Helianthus tuberosus
Helichrysum italicum
Heracleum sphondylium
Hibiscus sabbariffa
Hibiscus taiwanensis
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hornstedtia reticulata
Hylocereus undatus
Hypericum laricifolium
Hyssopus officinalis L.FooDB
Illicium verum
Impatiens balsamina
Ipomoea aquatica
Ipomoea batatas
Ipomoea nil
Iris ensata
Isodon japonicus
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.FooDB
Juglans regiaFooDB
Kalanchoe pinnata
Kigelia africana
Lablab purpureus
Lactuca sativaFooDB
Lagenaria siceraria
Larix sibirica
Lathyrus sativus
Laurus nobilis L.
Lens culinarisFooDB
Lentinus edodes
Lepidium sativum
Levisticum officinaleFooDB
Ligularia nelumbifolia
Ligularia veitchiana
Ligusticum multivittatum
Ligusticum porteri
Linum usitatissimumFooDB
Litchi chinensis
Lithospermum erythrorhizon
Luffa aegyptiaca
Lupinus
Lupinus albus
Macadamia
Macadamia tetraphylla
Macaranga triloba
Mallotus metcalfianus
Malpighia emarginata
Malus
Malus domestica
Malus pumilaFooDB
Mammea americana
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Marrubium cylleneum
Matricaria chamomilla
Matricaria recutitaFooDB
Matteuccia struthiopteris
Medicago sativa
Melissa officinalis L.FooDB
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicataFooDB
Mentha x piperita
Mespilus germanica
Metroxylon sagu
Michelia compressa
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigraFooDB
Murraya paniculata
Musa acuminata
Musa x paradisiaca
Myrica
Myristica fragrans
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
Notopterygium franchetii
Nuphar lutea
Ocimum basilicumFooDB
Oenanthe javanica
Oenothera biennisFooDB
Olea europaeaFooDB
Opuntia
Opuntia cochenillifera
Opuntia ficus-indica
Opuntia macrorhiza
Origanum majoranaFooDB
Origanum onites
Origanum vulgareFooDB
Origanum X majoricum
Oryza rufipogon
Oryza sativaFooDB
Pachyrhizus erosus
Panax ginseng
Pangium edule
Panicum miliaceum
Passiflora edulis
Pastinaca sativa
Pediomelum esculentum
Peperomia heyneana
Perideridia oregana
Persea americana
Petasites formosanus
Petasites japonicus
Petroselinum crispumFooDB
Petunia axillaris
Phaseolus coccineus
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phedimus kamtschaticus
Phellodendron amurense
Phellodendron chinense
Phoenix dactyliferaFooDB
Photinia melanocarpa
Phragmites australis
Phyllostachys edulisFooDB
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Picea glauca
Picea neoveitchii
Pimenta dioica
Pimpinella anisumFooDB
Pinus
Pinus edulis
Piper nigrum L.
Pistacia vera
Pisum sativumFooDB
Plantago major
Pleurotus ostreatus
Polygonum alpinum
Populus tremuloides
Portulaca oleraceaFooDB
Posidonia oceanica
Pouteria sapota
Prunus africana
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersica
Prunus persica var. persicaFooDB
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Pterogyne nitens
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifolia
Quercus
Quercus ilex
Ranunculus sieboldii
Raphanus sativusFooDB
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Reseda muricata
Rheum rhabarbarumFooDB
Rhodiola heterodonta
Ribes aureum
Ribes glandulosum
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Rorippa indica
Rosa
Rubus arcticus
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sabia japonica
Sagittaria latifolia
Salix pulchra
Salvia elegans
Salvia fruticosa
Salvia hispanica
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.
Sargentodoxa cuneata
Satureja hortensis L.
Satureja montana
Scorzonera hispanica
Scrophularia buergeriana
Scutellaria albida
Secale cerealeFooDB
Sechium edule
Sesamum indicumFooDB
Sesbania bispinosa
Silphium perfoliatum
Sinapis alba
Sisymbrium
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoense
Solanum tuberosumFooDB
Sophora alopecuroides
Sorbus aucuparia
Sorghum bicolor
Sparganium stoloniferum
Spinacia oleraceaFooDB
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Tamarix aphylla
Taraxacum mongolicum
Taraxacum officinaleFooDB
Tetragonia tetragonioides
Thelesperma
Theobroma cacaoFooDB
Thymus pulegioides
Thymus vulgarisFooDB
Tilia cordata
Tilia L.
Tragopogon porrifolius
Trigonella foenum-graecumFooDB
Triticum
Triticum aestivumFooDB
Triticum durumFooDB
Triticum spelta
Triticum turanicum
Triticum turgidum
Typha angustifolia
Vaccinium
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreum
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottii
Vaccinium macrocarponFooDB
Vaccinium myrtilloides
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosumFooDB
Vaccinium vitis-idaea
Valeriana laxiflora
Valerianella locusta
Vanilla
Verbena officinalis
Verbesina gigantea
Viburnum dilatatum
Viburnum edule
Vicia fabaFooDB
Vigna aconitifolia
Vigna angularis
Vigna mungo
Vigna radiataFooDB
Vigna umbellata
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
Viscum album
Viscum coloratum
Vitex agnus-castus
Vitis
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera
Vitis vinifera L.FooDB
Xanthium strumarium
Xanthorhiza simplicissima
Xanthosoma sagittifolium
Zea mays
Zea mays L.FooDB
Zingiber officinaleFooDB
Zizania
Zizania aquatica
Ziziphora clinopodioides
Ziziphus zizyphus
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-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
logP1.58ALOGPS
logP1.67ChemAxon
logS-2.3ALOGPS
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
Polarizability19.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000954
DrugBank IDDB07767
Phenol Explorer Compound ID499
FoodDB IDFDB030860
KNApSAcK IDC00002743
Chemspider ID393368
KEGG Compound IDC01494
BioCyc IDFERULIC-ACID
BiGG IDNot Available
Wikipedia LinkFerulic_Acid
METLIN ID4156
PubChem Compound445858
PDB IDNot Available
ChEBI ID17620
Good Scents IDrw1044121
References
General References
  1. Szutowska J, Gwiazdowska D, Rybicka I, Pawlak-Lemanska K, Bieganska-Marecik R, Gliszczynska-Swiglo A: Controlled fermentation of curly kale juice with the use of autochthonous starter cultures. Food Res Int. 2021 Nov;149:110674. doi: 10.1016/j.foodres.2021.110674. Epub 2021 Aug 28. [PubMed:34600676 ]
  2. Chen J, Wang Y, Wang S, Zhao X, Zhao L, Wang Y: Salvianolic acid B and ferulic acid synergistically promote angiogenesis in HUVECs and zebrafish via regulating VEGF signaling. J Ethnopharmacol. 2022 Jan 30;283:114667. doi: 10.1016/j.jep.2021.114667. Epub 2021 Sep 29. [PubMed:34597652 ]
  3. Guo X, Yu X, Zheng B, Zhang L, Zhang F, Zhang Y, Li J, Pu G, Zhang L, Wu H: Network Pharmacology-Based Identification of Potential Targets of Lonicerae japonicae Flos Acting on Anti-Inflammatory Effects. Biomed Res Int. 2021 Sep 20;2021:5507003. doi: 10.1155/2021/5507003. eCollection 2021. [PubMed:34595237 ]
  4. Yin X, Liu W, Chen H, Qi C, Chen H, Niu H, Yang J, Kwok KWH, Dong W: Effects of ferulic acid on muscle development and intestinal microbiota of zebrafish. J Anim Physiol Anim Nutr (Berl). 2022 Mar;106(2):429-440. doi: 10.1111/jpn.13631. Epub 2021 Sep 27. [PubMed:34580932 ]