NP-MRD: Showing NP-Card for (E)-caffeic acid (NP0031100)

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Record Information

Version

1.0

Created at

2021-06-19 22:16:38 UTC

Updated at

2021-08-20 00:00:22 UTC

NP-MRD ID

NP0031100

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(E)-caffeic acid

Provided By

JEOL Database JEOL Logo

Description

Caffeic acid, also known as trans-caffeate or sodium caffeate, 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. Caffeic acid has been detected, but not quantified in, several different foods, such as breakfast cereal, arabica coffees (Coffea arabica), peanuts (Arachis hypogaea), yellow wax beans (Phaseolus vulgaris), and fruits. This could make caffeic acid a potential biomarker for the consumption of these foods. Caffeic 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. (E)-caffeic acid is found in Abies spectabilis, Abutilon indicum, Acalypha australis, Acanthospermum australe, Achyrocline alata, Achyrocline flaccida, Achyrocline satureioides, Achyrocline tomentosa, Actaea cimicifuga, Actaea dahurica, Actaea simplex, Adenocaulon himalaicum, Ageratina glechonophylla, Ajania fruticulosa, Alchemilla tianschanica, Aleuritopteris formosana, Alibertia macrophylla, Aloe castellorum, Alsophila spinulosa, Althaea armeniaca, Althaea officinalis, Amelanchier sanguinea, Anchusa strigosa, Androsace septentrionalis, Anemone cernua, Angelica pubescens, Antennaria dioica, Antennaria microphylla, Anthoceros punctatus, Apis mellifera, Aralia continentalis, Arbutus unedo, Aristolochia heterophylla, Armeria maritima, Artemisia absinthium, Artemisia cina, Artemisia gmelinii, Artemisia rubripes, Artemisia scoparia, Artemisia sieversiana, Arum maculatum, Aspalathus linearis, Galium odoratum, Astragalus asper, Astragalus membranaceus, Astragalus wagneri, Avena sativa, Balanophora laxiflora, Balanophora tobiracola, Balbisia calycina, Berberis integerrima, Betonica officinalis, Betula pubescens, Betula obscura, Bistorta officinalis, Brassica napus, Brassica oleracea, Brassica rapa, Brickellia californica, Buddleja asiatica, Cacalia hastata, Cajanus cajan, Calliandra haematocephala, Callisia fragrans, Calluna vulgaris, Camchaya loloana, Campanula persicifolia, Canna indica, Caragana spinosa, Carthamus tinctorius, Castanea dentata, Centaurea cyanus, Centaurea jacea, Centaurea pseudomaculosa, Cephalaria gigantea, Cestrum parqui, Chelidonium majus, Chondrilla juncea, Tanacetum coccineum, Glebionis coronaria, Chrysanthemum morifolium, Leucanthemum vulgare, Cinchona pubescens, Citrus aurantium, Clematis vitalba, Colchicum kotschyi, Plectranthus scutellarioides, Convolvulus microphyllus, Corchorus capsularis, Cordia sebestena, Coriandrum sativum, Cotoneaster orbicularis, Crataegus laevigata, Crataegus rhipidophylla, Crepis vesicaria, Crinum asiaticum, Croton menthodorus, Cuscuta chinensis, Cyamopsis tetragonoloba, Cyclocarya paliurus, Cynara cardunculus, Cynara cornigera, Davallia mariesii, Dipsacus inermis, Dolichlasium lagascae, Echinacea angustifolia, Echinacea purpurea, Elaeagnus angustifolia, Eleutherococcus senticosus, Elsholtzia bodinieri, Ephedra foeminea, Equisetum arvense, Eremochloa ophiuroides, Erica arborea, Erigeron breviscapus, Erigeron canadensis, Erodium moschatum, Eryngium campestre, Eschenbachia blinii, Euonymus alatus, Eupatorium cannabinum, Euphorbia hirta, Euphorbia tithymaloides, Euphrasia stricta, Festuca ovina, Fibraurea tinctoria, Ficaria verna, Forsythia suspensa, Fraxinus ornus, Fumaria officinalis, Fumaria vaillantii, Galinsoga parviflora, Galinsoga quadriradiata, Galium palustre, Gardenia jasminoides, Gaultheria procumbens, Scorzonera latifolia, Geranium pusillum, Geranium robertianum, Geum japonicum, Geum rivale, Ginkgo biloba, Glechoma hederacea, Gonocaryum calleryanum, Haematoxylum brasiletto, Haematoxylum campechianum, Halocharis hispida, Hamamelis virginiana, Harpagophytum zeyheri, Hedeoma drummondii, Hedera helix, Hedera hibernica, Hedera rhombea, Sorbus thuringiaca, Helianthus annuus, Helichrysum arenarium, Helichrysum italicum, Helichrysum stoechas, Heliopsis helianthoides, Helleborus atrorubens, Hieracium gymnocephalum, Houttuynia cordata, Hydrophyllum tenuipes, Hylotelephium populifolium, Hypericum hirsutum, Hypericum perforatum, Hypericum sampsonii, Hypericum ternum, Ilex brevicuspis, Ilex hainanensis, Ilex pubescens, Ipomoea nil, Ipomoea orizabensis, Isodon japonicus, Isodon sculponeatus, Ixora javanica, Kalanchoe delagoensis, Kalanchoe pinnata, Kandelia candel, Keiskea japonica, Kigelia africana, Lactuca formosana, Lactuca viminea, Lagerstroemia speciosa, Lamium amplexicaule, Lantana trifolia, Lapsana communis, Larix sibirica, Lasthenia californica, Lavandula angustifolia, Leontodon taraxacoides, Lepidaploa remotiflora, Leucanthemum maximum, Ligularia dentata, Ligularia nelumbifolia, Ligularia pleurocaulis, Ligustrum japonicum, Ligustrum obtusifolium, Linaria macroura, Lonicera bournei, Lotus creticus, Lychnophora pinaster, Lycopus europaeus, Lythrum salicaria, Malus domestica, Malus sylvestris, Manihot esculenta, Matteuccia struthiopteris, Matthiola incana, Melissa officinalis, Menyanthes trifoliata, Monascus pilosus, Morella rubra, Morina nepalensis var. alba, Mosla chinensis, Murraya euchrestifolia, Mus musculus, Myosotis scorpioides, Myrica gale, Myrtus communis, Nardostachys jatamansi, Ocimum tenuiflorum, Oenothera elata, Oenothera speciosa, Ophioceras dolichostomum, Origanum dictamnus, Osmanthus fortunei, Osmanthus fragrans, Osmanthus heterophyllus, Ostericum grosseserratum, Oxalis pes-caprae, Oxyphyllum ulicinum, Panzerina lanata, Paronychia kapela, Paulownia tomentosa, Pavetta indica, Pelargonium incrassatum, Perilla frutescens, Persicaria lapathifolia, Petasites formosanus, Petasites japonicus, Petunia axillaris, Phedimus kamtschaticus, Phyllostachys nigra, Picea obovata, Pinus pinaster, Plantago depressa, Platanus orientalis, Poa huecu, Populus canadensis, Populus ciliata, Populus euphratica, Populus laurifolia, Populus nigra, Populus suaveolens, Populus szechuanica, Populus tremuloides, Populus yunnanensis, Potentilla erecta, Dasiphora fruticosa, Protea obtusifolia, Prunella vulgaris, Prunus serrulata, Pyrrosia petiolosa, Pyrus calleryana, Quercus ilex, Quercus suber, Reichardia tingitana, Reseda muricata, Rhodiola crenulata, Rhodiola rosea, Rhododendron ponticum, Salix cheilophila, Salvia przewalskii, Salvia trijuga, Salvia viridis, Salvinia molesta, Sanicula graveolens, Scolochloa festucacea, Scrophularia frutescens, Scrophularia nodosa, Scutellaria albida, Secamone afzelii, Sempervivum ruthenicum, Senna obtusifolia, Sibiraea angustata, Silphium integrifolium, Silphium perfoliatum, Smilax corbularia, Solanum angustifolium, Solanum cernuum, Solanum incanum, Solanum lyratum, Solanum nigrum, Solidago canadensis, Solidago virgaurea, Sonchus maritimus, Spathodea campanulata, Stachys palustris, Stereospermum acuminatissimum, Streptocaulon juventas, Symphyotrichum salignum, Symphytum officinale, Symplocarpus renifolius, Syringa reticulata, Tagetes lucida, Tanacetum corymbosum, Tecoma stans, Thalictrum atriplex, Tocoyena formosa, Tragopogon orientalis, Triticum turgidum, Tropicoporus linteus, Trypanosoma brucei, Typha domingensis, Urospermum picroides, Vaccinium dunalianum, Valeriana amurensis, Viburnum dilatatum, Viburnum opulus, Vincetoxicum scandens, Viscum album, Vitis vinifera and Ziziphora clinopodioides. It was first documented in 1994 (PMID: 8087979). Based on a literature review a significant number of articles have been published on Caffeic acid (PMID: 10706426) (PMID: 16614403) (PMID: 12207832) (PMID: 11479533).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100163D          

 21 21  0  0  0  0            999 V2000
    1.6454   -2.0982    1.1823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -1.7851    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -1.9289    1.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963   -1.2184   -0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.9823   -1.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7937   -0.4310   -2.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562   -0.8169   -3.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767   -0.3056   -4.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340    0.6047   -5.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944    1.1419   -6.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9880    1.0041   -4.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694    1.9080   -5.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8618    0.5012   -3.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395   -2.3057    1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3865   -1.0236   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936   -1.2211   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -1.5302   -3.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -0.6279   -5.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726    0.7710   -7.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601    2.1161   -5.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    0.8536   -2.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  1  0  0  0  0
  6  5  1  0  0  0  0
 13  6  2  0  0  0  0
  5  4  2  0  0  0  0
  9 11  2  0  0  0  0
  4  2  1  0  0  0  0
  6  7  1  0  0  0  0
  2  3  1  0  0  0  0
  7  8  2  0  0  0  0
  2  1  2  0  0  0  0
  8 18  1  0  0  0  0
 13 21  1  0  0  0  0
  7 17  1  0  0  0  0
 10 19  1  0  0  0  0
 12 20  1  0  0  0  0
  5 16  1  0  0  0  0
  4 15  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031100

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

> <INCHI_KEY>
QAIPRVGONGVQAS-DUXPYHPUSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.335364136589572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.5289556166666665

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.276437669500657

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6438401388538604

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283746523508147

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
47.021699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caffeic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       1.645  -2.098   1.182  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.655  -1.785   0.551  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.585  -1.929   1.045  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.596  -1.218  -0.802  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.735  -0.982  -1.471  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.794  -0.431  -2.832  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.856  -0.817  -3.669  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.977  -0.306  -4.966  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.034   0.605  -5.423  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.094   1.142  -6.679  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.988   1.004  -4.597  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.069   1.908  -5.051  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.862   0.501  -3.308  0.00  0.00           C+0
HETATM   14  H   UNK     0      -0.440  -2.306   1.938  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.387  -1.024  -1.211  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.694  -1.221  -1.013  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.599  -1.530  -3.316  0.00  0.00           H+0
HETATM   18  H   UNK     0       3.804  -0.628  -5.590  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.873   0.771  -7.129  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.360   2.116  -5.961  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.043   0.854  -2.688  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   14                                                       
CONECT    4    5    2   15                                                  
CONECT    5    6    4   16                                                  
CONECT    6    5   13    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    9    7   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   19                                                       
CONECT   11   13   12    9                                                  
CONECT   12   11   20                                                       
CONECT   13   11    6   21                                                  
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16    5                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19   10                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydroxy-trans-cinnamate	ChEBI
3,4-Dihydroxycinnamic acid	ChEBI
trans-Caffeate	ChEBI
3,4-Dihydroxy-trans-cinnamic acid	Generator
3,4-Dihydroxycinnamate	Generator
trans-Caffeic acid	Generator
Caffeate	Generator
Caffeic acid, monosodium salt	HMDB
Caffeic acid, (e)-isomer	HMDB
Sodium caffeate	HMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3,4-Dihydroxycinnamic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acid	HMDB
(e)-Caffeic acid	HMDB
3,4-Dihydroxybenzeneacrylic acid	HMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
3-(3,4-Dihydroxyphenyl)propenoic acid	HMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene	HMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene	HMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzene	HMDB
DHCA	HMDB
trans-3,4-Dihydroxycinnamic acid	HMDB
3',4'-Dihydroxycinnamic acid	HMDB
3-(3,4-Dihydroxyphenyl)acrylic acid	HMDB
CAFFEIC ACID	ChEBI
Caffeic acid	HMDB

Chemical Formula

C₉H₈O₄

Average Mass

180.1574 Da

Monoisotopic Mass

180.04226 Da

IUPAC Name

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Traditional Name

caffeic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\[H])=C(/[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

InChI Key

QAIPRVGONGVQAS-DUXPYHPUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies spectabilis	LOTUS Database	35616633
Abutilon indicum	LOTUS Database	35616633
Acalypha australis	LOTUS Database	35616633
Acanthospermum australe	LOTUS Database	35616633
Achillea millefolium	KNApSAcK Database	22123792
Achyrocline alata	LOTUS Database	35616633
Achyrocline flaccida	LOTUS Database	35616633
Achyrocline satureioides	LOTUS Database	35616633
Achyrocline tomentosa	LOTUS Database	35616633
Actaea cimicifuga	LOTUS Database	35616633
Actaea dahurica	LOTUS Database	35616633
Actaea racemosa	KNApSAcK Database	22123792
Actaea simplex	LOTUS Database	35616633
Actinidia arguta	KNApSAcK Database	22123792
Actinidia callosa var.henryi	KNApSAcK Database	22123792
Actinidia chinensis	KNApSAcK Database	22123792
Actinidia chrysantha	KNApSAcK Database	22123792
Actinidia deliciosa	KNApSAcK Database	22123792
Actinidia eriantha	KNApSAcK Database	22123792
Actinidia glaucophylla	KNApSAcK Database	22123792
Actinidia latifolia	KNApSAcK Database	22123792
Actinidia polygana	KNApSAcK Database	22123792
Adenocaulon adhaerescens	KNApSAcK Database	22123792
Adenocaulon himalaicum	LOTUS Database	35616633
Aeschynomene americana	KNApSAcK Database	22123792
Ageratina glechonophylla	LOTUS Database	35616633
Agrimonia pilosa var.japonica	KNApSAcK Database	22123792
Ajania fruticulosa	LOTUS Database	35616633
Alchemilla tianschanica	LOTUS Database	35616633
Aleuritopteris formosana	LOTUS Database	35616633
Alibertia macrophylla	LOTUS Database	35616633
Allium ampeloprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium fistulosum	FooDB	PHENOL EXPLORER
Allium sativum	KNApSAcK Database	22123792
Allium schoenoprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Aloe castellorum	LOTUS Database	35616633
Alsophila spinulosa	LOTUS Database	35616633
Althaea armeniaca	LOTUS Database	35616633
Althaea officinalis	LOTUS Database	35616633
Amelanchier sanguinea	LOTUS Database	35616633
Amphibolis antarctica	KNApSAcK Database	22123792
Amphibolis griffithii	KNApSAcK Database	22123792
Ananas comosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anchusa strigosa	LOTUS Database	35616633
Andrographis paniculata	KNApSAcK Database	22123792
Androsace septentrionalis	LOTUS Database	35616633
Anemone cernua	LOTUS Database	35616633
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Angelica pubescens	LOTUS Database	35616633
Anigozanthos preissii	KNApSAcK Database	22123792
Annona muricata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anser anser	FooDB	FooDB
Antennaria dioica	LOTUS Database	35616633
Antennaria microphylla	LOTUS Database	35616633
Anthemis nobilis	KNApSAcK Database	22123792
Anthoceros punctatus	LOTUS Database	35616633
Apis mellifera	LOTUS Database	35616633
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis glabrata	KNApSAcK Database	22123792
Arachis hypogaea	KNApSAcK Database	22123792
Aralia continentalis	LOTUS Database	35616633
Arbutus unedo	LOTUS Database	35616633
Arctium lappa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Aristolochia heterophylla	LOTUS Database	35616633
Armeria maritima	LOTUS Database	35616633
Armoracia rusticana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia absinthium	LOTUS Database	35616633
Artemisia capillaris	KNApSAcK Database	22123792
Artemisia cina	LOTUS Database	35616633
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia gmelinii	LOTUS Database	35616633
Artemisia minor	KNApSAcK Database	22123792
Artemisia rubripes	LOTUS Database	35616633
Artemisia scoparia	LOTUS Database	35616633
Artemisia sieversiana	LOTUS Database	35616633
Arum maculatum	LOTUS Database	35616633
Aruncus diocus	KNApSAcK Database	22123792
Aspalathus linearis	LOTUS Database	35616633
Asperula odorata	LOTUS Database	35616633
Aster salignus	KNApSAcK Database	22123792
Astragalus arguricus	KNApSAcK Database	22123792
Astragalus asper	LOTUS Database	35616633
Astragalus ciceroides	KNApSAcK Database	22123792
Astragalus flexus	KNApSAcK Database	22123792
Astragalus floccosifolius	KNApSAcK Database	22123792
Astragalus levieri	KNApSAcK Database	22123792
Astragalus membranaceus	LOTUS Database	35616633
Astragalus onobrychis	KNApSAcK Database	22123792
Astragalus quisqualis	KNApSAcK Database	22123792
Astragalus saganlugensis	KNApSAcK Database	22123792
Astragalus wagneri	LOTUS Database	35616633
Avena sativa	LOTUS Database	35616633
Avena sativa L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Balanophora japonica	KNApSAcK Database	22123792
Balanophora laxiflora	LOTUS Database	35616633
Balanophora tobiracola	LOTUS Database	35616633
Balbisia calycina	LOTUS Database	35616633
Begonia nantoensis	KNApSAcK Database	22123792
Berberis integerrima	LOTUS Database	35616633
Beta vulgaris	KNApSAcK Database	22123792
Beta vulgaris ssp. cicla	FooDB	PHENOL EXPLORER
Betonica officinalis	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Betula x obscura	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bistorta officinalis	LOTUS Database	35616633
Blechnum orientale	KNApSAcK Database	22123792
Boehmeria holosericea	KNApSAcK Database	22123792
Boehmeria tricuspis	KNApSAcK Database	22123792
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brainea insignis	KNApSAcK Database	22123792
Brassica napus	LOTUS Database	35616633
Brassica oleracea	LOTUS Database	35616633
Brassica oleracea var. botrytis	FooDB	PHENOL EXPLORER
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gemmifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gongylodes	KNApSAcK Database	22123792
Brassica oleracea var. italica	FooDB	9416471
Brassica rapa	LOTUS Database	35616633
Brassica rapa var. rapa	FooDB	PHENOL EXPLORER
Brickellia californica	LOTUS Database	35616633
Bryophyllum pinnatum	KNApSAcK Database	22123792
Bubalus bubalis	FooDB	FooDB
Buddleja asiatica	LOTUS Database	35616633
Cacalia hastata	LOTUS Database	35616633
Cajanus cajan	LOTUS Database	35616633
Calliandra haematocephala	LOTUS Database	35616633
Calligonum leucocladum	KNApSAcK Database	22123792
Callisia fragrans	LOTUS Database	35616633
Calluna vulgaris	LOTUS Database	35616633
Camchaya loloana	LOTUS Database	35616633
Campanula persicifolia	LOTUS Database	35616633
Canna indica	LOTUS Database	35616633
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Caragana spinosa	LOTUS Database	35616633
Carica papaya	KNApSAcK Database	22123792
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Carthamus tinctorius	LOTUS Database	35616633
Carum carvi	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Castanea dentata	LOTUS Database	35616633
Castanea sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Centaurea bracteata Scop.	KNApSAcK Database	22123792
Centaurea cyanus	LOTUS Database	35616633
Centaurea jacea	LOTUS Database	35616633
Centaurea pseudomaculosa	LOTUS Database	35616633
Cephalaria gigantea	LOTUS Database	35616633
Ceratostigma willmottianum	KNApSAcK Database	22123792
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Cestrum parqui	LOTUS Database	35616633
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chelidonium majus	LOTUS Database	35616633
Chondrilla juncea	LOTUS Database	35616633
Chrysanthemum coccineum	LOTUS Database	35616633
Chrysanthemum coronarium	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Chrysanthemum vulgare	LOTUS Database	35616633
Cibotium barometz	KNApSAcK Database	22123792
Cicer arietinum	KNApSAcK Database	22123792
Cichorium endivia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cichorium intybus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cimicifuga dahurica	KNApSAcK Database	22123792
Cimicifuga foetida	KNApSAcK Database	22123792
Cinchona cuprea	KNApSAcK Database	22123792
Cinchona pubescens	LOTUS Database	35616633
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrullus lanatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus aurantium	LOTUS Database	35616633
Citrus limon	KNApSAcK Database	22123792
Citrus paradisi	FooDB	PHENOL EXPLORER
Citrus sinensis	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clematis vitalba	LOTUS Database	35616633
Coffea arabica	KNApSAcK Database	22123792
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Colchicum kotschyi	LOTUS Database	35616633
Coleus blumei	LOTUS Database	35616633
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Conium maculatum	KNApSAcK Database	22123792
Convolvulus microphyllus	LOTUS Database	35616633
Conyza blinii	KNApSAcK Database	22123792
Corchorus capsularis	LOTUS Database	35616633
Cordia macleodii	KNApSAcK Database	22123792
Cordia sebestena	LOTUS Database	35616633
Coriandrum sativum	LOTUS Database	35616633
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cotoneaster orbicularis	LOTUS Database	35616633
Crataegus laevigata	LOTUS Database	35616633
Crataegus pinnatifida	KNApSAcK Database	22123792
Crataegus rhipidophylla	LOTUS Database	35616633
Crepis vesicaria	LOTUS Database	35616633
Crinum asiaticum	LOTUS Database	35616633
Croton menthodorus	LOTUS Database	35616633
Cucumis melo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita	FooDB	PHENOL EXPLORER
Cuminum cyminum	FooDB	PHENOL EXPLORER
Curcuma longa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cuscuta australis	KNApSAcK Database	22123792
Cuscuta chinensis	LOTUS Database	35616633
Cyamopsis tetragonoloba	LOTUS Database	35616633
Cyclocarya paliurus	LOTUS Database	35616633
Cymodocea rotundata	KNApSAcK Database	22123792
Cymodocea serrulata	KNApSAcK Database	22123792
Cynara cardunculus	LOTUS Database	35616633
Cynara cornigera	LOTUS Database	35616633
Datura innoxia	KNApSAcK Database	22123792
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Davallia mariesii	LOTUS Database	35616633
Dichrocephala bicolor	KNApSAcK Database	22123792
Digitalis purpurea	KNApSAcK Database	22123792
Dipsacus asper	KNApSAcK Database	22123792
Dipsacus inermis	LOTUS Database	35616633
Dodonaea viscosa	KNApSAcK Database	22123792
Dolichlasium lagascae	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Echinacea angustifolia	LOTUS Database	35616633
Echinacea purpurea	LOTUS Database	35616633
Elaeagnus angustifolia	LOTUS Database	35616633
Elettaria cardamomum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Eleutherococcus senticosus	LOTUS Database	35616633
Elsholtzia bodinieri	LOTUS Database	35616633
Elsholtzia rugulosa Hemsl.	KNApSAcK Database	22123792
Ephedra foeminea	LOTUS Database	35616633
Ephedra sinica	KNApSAcK Database	22123792
Equisetum arvense	LOTUS Database	35616633
Equisetum hiemale	KNApSAcK Database	22123792
Equus caballus	FooDB	FooDB
Eremochloa ophiuroides	LOTUS Database	35616633
Erica arborea	LOTUS Database	35616633
Erigeron breviscapus	LOTUS Database	35616633
Erigeron canadensis	LOTUS Database	35616633
Eriobotrya japonica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Erodium moschatum	LOTUS Database	35616633
Eryngium campestre	LOTUS Database	35616633
Eryngium yuccifolium	KNApSAcK Database	22123792
Erythrina variegata	KNApSAcK Database	22123792
Eschenbachia blinii	LOTUS Database	35616633
Eucalyptus globulus	KNApSAcK Database	22123792
Eucommia ulmoides	KNApSAcK Database	22123792
Euonymus alatus	LOTUS Database	35616633
Eupatorium cannabinum	LOTUS Database	35616633
Euphorbia hirta	LOTUS Database	35616633
Euphorbia tithymaloides	LOTUS Database	35616633
Euphrasia stricta	LOTUS Database	35616633
Evolvulus alsinoides	KNApSAcK Database	22123792
Fagopyrum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Falcaria vulgaris	KNApSAcK Database	22123792
Festuca ovina	LOTUS Database	35616633
Fibraurea tinctoria	LOTUS Database	35616633
Ficaria verna	LOTUS Database	35616633
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Forsythia intermedia	KNApSAcK Database	22123792
Forsythia suspensa	LOTUS Database	35616633
Fragaria x ananassa	FooDB	PHENOL EXPLORER
Fraxinus ornus	LOTUS Database	35616633
Fumaria officinalis	LOTUS Database	35616633
Fumaria vaillantii	LOTUS Database	35616633
Galinsoga parviflora	LOTUS Database	35616633
Galinsoga quadriradiata	LOTUS Database	35616633
Galium palustre	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Gardenia jasminoides	LOTUS Database	35616633
Gaultheria procumbens	LOTUS Database	35616633
Gaylussacia baccata	FooDB	PHENOL EXPLORER
Gelasia latifolia	LOTUS Database	35616633
Geranium pusillum	LOTUS Database	35616633
Geranium robertianum	LOTUS Database	35616633
Geum japonicum	LOTUS Database	35616633
Geum rivale	LOTUS Database	35616633
Ginkgo biloba	LOTUS Database	35616633
Glechoma hederacea	LOTUS Database	35616633
Glehnia littoralis	KNApSAcK Database	22123792
Glycine max	KNApSAcK Database	22123792
Gonocaryum calleryanum	LOTUS Database	35616633
Gossypium barbadense	KNApSAcK Database	22123792
Haematoxylum brasiletto	LOTUS Database	35616633
Haematoxylum campechianum	LOTUS Database	35616633
Halocharis hispida	LOTUS Database	35616633
Halodule uninervis	KNApSAcK Database	22123792
Halodule wrightii	KNApSAcK Database	22123792
Halophila engelmannii	KNApSAcK Database	22123792
Halophila hawaiiana	KNApSAcK Database	22123792
Halophila minor	KNApSAcK Database	22123792
Hamamelis virginiana	LOTUS Database	35616633
Harpagophytum procumbens	KNApSAcK Database	22123792
Harpagophytum zeyheri	LOTUS Database	35616633
Hedeoma drummondii	LOTUS Database	35616633
Hedera helix	LOTUS Database	35616633
Hedera hibernica	LOTUS Database	35616633
Hedera rhombea	LOTUS Database	35616633
Hedlundia x thuringiaca	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helichrysum arenarium	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Helichrysum stoechas	LOTUS Database	35616633
Heliopsis helianthoides	LOTUS Database	35616633
Helleborus atrorubens	LOTUS Database	35616633
Hibiscus taiwanensis	KNApSAcK Database	22123792
Hieracium gymnocephalum	LOTUS Database	35616633
Hippophae rhamnoides	FooDB	PHENOL EXPLORER
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Houttuynia cordata	LOTUS Database	35616633
Humulus lupulus	KNApSAcK Database	22123792
Hydrophyllum tenuipes	LOTUS Database	35616633
Hylotelephium populifolium	LOTUS Database	35616633
Hypericum hirsutum	LOTUS Database	35616633
Hypericum laricifolium	KNApSAcK Database	22123792
Hypericum perforatum	LOTUS Database	35616633
Hypericum sampsonii	LOTUS Database	35616633
Hypericum ternum	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ilex brevicuspis	LOTUS Database	35616633
Ilex chinensis	KNApSAcK Database	22123792
Ilex hainanensis	LOTUS Database	35616633
Ilex paraguariensis	KNApSAcK Database	22123792
Ilex pubescens	LOTUS Database	35616633
Illicium verum	FooDB	PHENOL EXPLORER
Inula britannica	KNApSAcK Database	22123792
Ipomoea batatas	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ipomoea nil	LOTUS Database	35616633
Ipomoea orizabensis	LOTUS Database	35616633
Isodon japonicus	LOTUS Database	35616633
Isodon sculponeatus	LOTUS Database	35616633
Ixora javanica	LOTUS Database	35616633
Juglans nigra L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans regia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Kalanchoe delagoensis	LOTUS Database	35616633
Kalanchoe pinnata	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Keiskea japonica	LOTUS Database	35616633
Kigelia africana	LOTUS Database	35616633
Lactuca formosana	LOTUS Database	35616633
Lactuca sativa	FooDB	16666434
Lactuca viminea	LOTUS Database	35616633
Lagerstroemia speciosa	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Lamium amplexicaule	LOTUS Database	35616633
Lantana trifolia	LOTUS Database	35616633
Lapsana communis L.	LOTUS Database	35616633
Larix sibirica	LOTUS Database	35616633
Lasthenia californica	LOTUS Database	35616633
Lathyrus spp.	KNApSAcK Database	22123792
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lavandula angustifolia	LOTUS Database	35616633
Leontodon taraxacoides	LOTUS Database	35616633
Lepidaploa remotiflora	LOTUS Database	35616633
Leporidae	FooDB	FooDB
Leptolaena diospyroidea	KNApSAcK Database	22123792
Leptolaena pauciflora	KNApSAcK Database	22123792
Lepus timidus	FooDB	FooDB
Lespedeza bicolor	KNApSAcK Database	22123792
Leucanthemum maximum	LOTUS Database	35616633
Levisticum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ligularia dentata	LOTUS Database	35616633
Ligularia nelumbifolia	LOTUS Database	35616633
Ligularia pleurocaulis	LOTUS Database	35616633
Ligusticum chuanxiong	KNApSAcK Database	22123792
Ligustrum japonicum	LOTUS Database	35616633
Ligustrum obtusifolium	LOTUS Database	35616633
Linaria macroura	LOTUS Database	35616633
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lithospermum erythrorhizon	KNApSAcK Database	22123792
Lonicera bournei Hemsl.	LOTUS Database	35616633
Lonicera fulvotomentosa	KNApSAcK Database	22123792
Lonicera japonica	KNApSAcK Database	22123792
Lonicera similis	KNApSAcK Database	22123792
Lotus corniculatus	KNApSAcK Database	22123792
Lotus creticus	LOTUS Database	35616633
Lotus japonicus	KNApSAcK Database	22123792
Lychnophora pinaster	LOTUS Database	35616633
Lycopus europaeus	LOTUS Database	35616633
Lythrum salicaria	LOTUS Database	35616633
Magnolia denudata	KNApSAcK Database	22123792
Magnolia liliiflora	KNApSAcK Database	22123792
Malus domestica	LOTUS Database	35616633
Malus pumila	FooDB	9818410
Malus sylvestris	LOTUS Database	35616633
Mangifera indica	KNApSAcK Database	22123792
Manihot esculenta	LOTUS Database	35616633
Matricaria chamomilla	KNApSAcK Database	22123792
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Matteuccia struthiopteris	LOTUS Database	35616633
Matthiola incana	LOTUS Database	35616633
Medicago sativa	KNApSAcK Database	22123792
Medicago truncatula	KNApSAcK Database	22123792
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Melilotus officinalis	KNApSAcK Database	22123792
Melissa officinalis	LOTUS Database	35616633
Melissa officinalis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha haplocalyx	KNApSAcK Database	22123792
Mentha piperitae	KNApSAcK Database	22123792
Mentha spicata	FooDB	PHENOL EXPLORER
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Menyanthes trifoliata	LOTUS Database	35616633
Momordica charantia	KNApSAcK Database	22123792
Monascus pilosus	LOTUS Database	35616633
Morella rubra	LOTUS Database	35616633
Morina nepalensis var. alba	JEOL database	Teng, R. W., et al, Magn. Reson. Chem. 43, 92 (2005)
Moringa oleifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mosla chinensis	LOTUS Database	35616633
Murraya euchrestifolia	LOTUS Database	35616633
Murraya paniculata	KNApSAcK Database	22123792
Mus musculus	LOTUS Database	35616633
Myosotis scorpioides	LOTUS Database	35616633
Myrica gale	LOTUS Database	35616633
Myristica fragrans	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Myrtus communis	LOTUS Database	35616633
Nardostachys jatamansi	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Ocimum basilicum	KNApSAcK Database	22123792
Ocimum sanctum	KNApSAcK Database	22123792
Ocimum tenuiflorum	LOTUS Database	35616633
Odocoileus	FooDB	FooDB
Oenothera biennis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Oenothera elata	LOTUS Database	35616633
Oenothera speciosa	LOTUS Database	35616633
Olea europaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Onobrychis arenaria	KNApSAcK Database	22123792
Onopordum acanthium	KNApSAcK Database	22123792
Ophioceras dolichostomum	LOTUS Database	35616633
Origanum dictamnus	LOTUS Database	35616633
Origanum majorana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum X majoricum	FooDB	PHENOL EXPLORER
Orthosiphon stamineus	KNApSAcK Database	22123792
Oryctolagus	FooDB	FooDB
Oryza sativa	FooDB	PHENOL EXPLORER
Osmanthus fortunei	LOTUS Database	35616633
Osmanthus fragrans	LOTUS Database	35616633
Osmanthus heterophyllus	LOTUS Database	35616633
Ostericum grosseserratum	LOTUS Database	35616633
Ovis aries	FooDB	FooDB
Oxalis pes-caprae	LOTUS Database	35616633
Oxyphyllum ulicinum	LOTUS Database	35616633
Panicum virgatum	KNApSAcK Database	22123792
Panzerina lanata	LOTUS Database	35616633
Papaver somniferum	KNApSAcK Database	22123792
Paronychia kapela	LOTUS Database	35616633
Paulownia tomentosa	LOTUS Database	35616633
Pavetta indica	LOTUS Database	35616633
Pelargonium incrassatum	LOTUS Database	35616633
Pelargonium reniforme	KNApSAcK Database	22123792
Pellia epiphylla	KNApSAcK Database	22123792
Perilla frutescens	LOTUS Database	35616633
Perilla frutescens var.acuta.	KNApSAcK Database	22123792
Persea americana	FooDB	F. W. Knapp. Some Characteristics of Eggplant and Avocado Poiyphenolases. J. Food Science. 30(6),...
Persicaria lapathifolia	LOTUS Database	35616633
Petasites formosanus	LOTUS Database	35616633
Petasites japonicus	LOTUS Database	35616633
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Petunia axillaris	LOTUS Database	35616633
Pharbitis nil	KNApSAcK Database	22123792
Phaseolus vulgaris	KNApSAcK Database	22123792
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phedimus kamtschaticus	LOTUS Database	35616633
Phellodendron japonicum MAXIM	KNApSAcK Database	22123792
Phlomis tuberosa	KNApSAcK Database	22123792
Phoenix dactylifera	FooDB	PHENOL EXPLORER
Photinia melanocarpa	FooDB	PHENOL EXPLORER
Phyllanthus sellowianus	KNApSAcK Database	22123792
Phyllospadix scouleri	KNApSAcK Database	22123792
Phyllospadix serrulatus	KNApSAcK Database	22123792
Phyllospadix torreyi	KNApSAcK Database	22123792
Phyllostachys nigra	LOTUS Database	35616633
Picea obovata	LOTUS Database	35616633
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pinus pinaster	LOTUS Database	35616633
Pinus sibirica	KNApSAcK Database	22123792
Pinus spp.	KNApSAcK Database	22123792
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pisum sativum	KNApSAcK Database	22123792
Plantago depressa	LOTUS Database	35616633
Plantago lanceolata	KNApSAcK Database	22123792
Plantago major	KNApSAcK Database	22123792
Plantago media	KNApSAcK Database	22123792
Platanus orientalis	LOTUS Database	35616633
Poa huecu	LOTUS Database	35616633
Polygonum aviculare	KNApSAcK Database	22123792
Populus canadensis	LOTUS Database	35616633
Populus ciliata	LOTUS Database	35616633
Populus deltoides	KNApSAcK Database	22123792
Populus euphratica	LOTUS Database	35616633
Populus laurifolia	LOTUS Database	35616633
Populus nigra	LOTUS Database	35616633
Populus pseudosimonii	KNApSAcK Database	22123792
Populus spp.	KNApSAcK Database	22123792
Populus suaveolens	LOTUS Database	35616633
Populus szechuanica	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633
Populus trichocarpa	KNApSAcK Database	22123792
Populus yunnanensis	LOTUS Database	35616633
Portulaca oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Posidonia australis	KNApSAcK Database	22123792
Posidonia oceanica	KNApSAcK Database	22123792
Potentilla erecta	LOTUS Database	35616633
Potentilla fruticosa	LOTUS Database	35616633
Protea obtusifolia	LOTUS Database	35616633
Prunella vulgaris	LOTUS Database	35616633
Prunus armeniaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus avium	KNApSAcK Database	22123792
Prunus cerasus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus domestica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus dulcis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica var. persica	FooDB	PHENOL EXPLORER
Prunus serrulata	LOTUS Database	35616633
Pteris multifida	KNApSAcK Database	22123792
Pterocaulon virgatum	KNApSAcK Database	22123792
Pueraria Phaseoloides	KNApSAcK Database	22123792
Punica granatum	KNApSAcK Database	22123792
Pyrrosia petiolosa	LOTUS Database	35616633
Pyrrosia sheareri	KNApSAcK Database	22123792
Pyrus communis	FooDB	18778075
Pyrus kawakamii	LOTUS Database	35616633
Quercus ilex	LOTUS Database	35616633
Quercus suber	LOTUS Database	35616633
Ranunculus baudotii	KNApSAcK Database	22123792
Raphanus sativus	KNApSAcK Database	22123792
Reichardia tingitana (L.) Roth	LOTUS Database	35616633
Reseda muricata	LOTUS Database	35616633
Reseda muricata C.Presl.	KNApSAcK Database	22123792
Rhaponticum carthamoides	KNApSAcK Database	22123792
Rheum rhabarbarum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rhodiola crenulata	LOTUS Database	35616633
Rhodiola crenulata (HOOK.f.et Thoms.) H.OHBA	KNApSAcK Database	22123792
Rhodiola rosea	LOTUS Database	35616633
Rhodiola sachalinensis	KNApSAcK Database	22123792
Rhodiola sacra	KNApSAcK Database	22123792
Rhododendron ponticum	LOTUS Database	35616633
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes rubrum	FooDB	PHENOL EXPLORER
Rosmarinus officinalis	KNApSAcK Database	22123792
Rubus chamaemorus	FooDB	PHENOL EXPLORER
Rubus idaeus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rubus occidentalis	FooDB	PHENOL EXPLORER
Salix cheilophila	LOTUS Database	35616633
Salvia albimaculata	KNApSAcK Database	22123792
Salvia bowleyana	KNApSAcK Database	22123792
Salvia calycina	KNApSAcK Database	22123792
Salvia chinensis	KNApSAcK Database	22123792
Salvia horminum	KNApSAcK Database	22123792
Salvia limbata	KNApSAcK Database	22123792
Salvia miltiorrhiza	KNApSAcK Database	22123792
Salvia officinalis	KNApSAcK Database	22123792
Salvia plebeia	KNApSAcK Database	22123792
Salvia przewalskii	LOTUS Database	35616633
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia sonchifolia	KNApSAcK Database	22123792
Salvia trijuga	LOTUS Database	35616633
Salvia triloba	KNApSAcK Database	22123792
Salvia viridis L.	LOTUS Database	35616633
Salvinia molesta	LOTUS Database	35616633
Salvinia molesta D.S.Mitch.	KNApSAcK Database	22123792
Sambucus formosana	KNApSAcK Database	22123792
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sanicula europaea	KNApSAcK Database	22123792
Sanicula graveolens	LOTUS Database	35616633
Sarcandra glabra	KNApSAcK Database	22123792
Satureja montana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Satureja subspicata	KNApSAcK Database	22123792
Scolochloa festucacea	LOTUS Database	35616633
Scrophularia buergeriana	KNApSAcK Database	22123792
Scrophularia frutescens	LOTUS Database	35616633
Scrophularia nodosa	LOTUS Database	35616633
Scutellaria albida	LOTUS Database	35616633
Scutellaria albida subsp.albida	KNApSAcK Database	22123792
Secale cereale	FooDB	PHENOL EXPLORER
Secamone afzelii	LOTUS Database	35616633
Sedum takesimense Nakai	KNApSAcK Database	22123792
Sempervivum ruthenicum	LOTUS Database	35616633
Senna obtusifolia	LOTUS Database	35616633
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sibiraea angustata	LOTUS Database	35616633
Sideritis catillaris	KNApSAcK Database	22123792
Silphium integrifolium	LOTUS Database	35616633
Silphium perfoliatum	LOTUS Database	35616633
Smilax corbularia	LOTUS Database	35616633
Solanum acaule	KNApSAcK Database	22123792
Solanum angustifolium	LOTUS Database	35616633
Solanum bulbocastanum	KNApSAcK Database	22123792
Solanum canasense	KNApSAcK Database	22123792
Solanum cardiophyllum	KNApSAcK Database	22123792
Solanum cernuum	LOTUS Database	35616633
Solanum chacoense	KNApSAcK Database	22123792
Solanum commersonii	KNApSAcK Database	22123792
Solanum fendleri	KNApSAcK Database	22123792
Solanum habrochaites	KNApSAcK Database	22123792
Solanum hougasii	KNApSAcK Database	22123792
Solanum incanum	LOTUS Database	35616633
Solanum lycopersicum	KNApSAcK Database	22123792
Solanum lycopersicum var. cerasiforme	FooDB	PHENOL EXPLORER
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum lyratum	LOTUS Database	35616633
Solanum melongena	FooDB	F. W. Knapp. Some Characteristics of Eggplant and Avocado Poiyphenolases. J. Food Science. 30(6),...
Solanum multidissectum	KNApSAcK Database	22123792
Solanum neorickii	KNApSAcK Database	22123792
Solanum nigrum	LOTUS Database	35616633
Solanum parviflorum	KNApSAcK Database	22123792
Solanum pennellii	KNApSAcK Database	22123792
Solanum phureja	KNApSAcK Database	22123792
Solanum pimpinellifollium	KNApSAcK Database	22123792
Solanum pinnacritisectum	KNApSAcK Database	22123792
Solanum tarijense	KNApSAcK Database	22123792
Solanum tuberosum	KNApSAcK Database	22123792
Solidago altissima L.	KNApSAcK Database	22123792
Solidago canadensis	LOTUS Database	35616633
Solidago virgaurea	LOTUS Database	35616633
Solidago virgaurea var.leiocarpa	KNApSAcK Database	22123792
Sonchus maritimus	LOTUS Database	35616633
Sophora flavescens	KNApSAcK Database	22123792
Sophora japonica	KNApSAcK Database	22123792
Spartium junceum	KNApSAcK Database	22123792
Spathodea campanulata	LOTUS Database	35616633
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Stachys palustris	LOTUS Database	35616633
Stereospermum acuminatissimum	LOTUS Database	35616633
Streptocaulon juventas	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Symphyotrichum x salignum	LOTUS Database	35616633
Symphytum officinale	LOTUS Database	35616633
Symplocarpus renifolius	LOTUS Database	35616633
Syringa reticulata	LOTUS Database	35616633
Syringodium filiforme	KNApSAcK Database	22123792
Syringodium isoetifolium	KNApSAcK Database	22123792
Syzygium aromaticum	FooDB	PHENOL EXPLORER
Tagetes lucida	LOTUS Database	35616633
Tanacetum corymbosum	LOTUS Database	35616633
Taraxacum formosanum	KNApSAcK Database	22123792
Taraxacum mongolicum	KNApSAcK Database	22123792
Taraxacum officinale	KNApSAcK Database	22123792
Taxus baccata	KNApSAcK Database	22123792
Tecoma stans	LOTUS Database	35616633
Tephrosia candida	KNApSAcK Database	22123792
Tephrosia purpurea	KNApSAcK Database	22123792
Tetrapleura tetraptera	KNApSAcK Database	22123792
Thalassia ciliatum	KNApSAcK Database	22123792
Thalassia hemprichii	KNApSAcK Database	22123792
Thalassia testudinum	KNApSAcK Database	22123792
Thalassodendron ciliatum	KNApSAcK Database	22123792
Thalictrum atriplex	LOTUS Database	35616633
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Thymus vulgaris	KNApSAcK Database	22123792
Tilia L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tocoyena formosa	LOTUS Database	35616633
Toona ciliata	KNApSAcK Database	22123792
Tragopogon orientalis	LOTUS Database	35616633
Trigonella foenum-graecum	FooDB	PHENOL EXPLORER
Triticum aestivum	KNApSAcK Database	22123792
Triticum durum	FooDB	PHENOL EXPLORER
Triticum turgidum	LOTUS Database	35616633
Tropicoporus linteus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633
Typha domingensis	LOTUS Database	35616633
Typha domingensis P.	KNApSAcK Database	22123792
Uncaria sinensis	KNApSAcK Database	22123792
Urospermum picroides	LOTUS Database	35616633
Urtica dioica	KNApSAcK Database	22123792
Vaccinium angustifolium	FooDB	PHENOL EXPLORER
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	PHENOL EXPLORER
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium deliciosum	FooDB	PHENOL EXPLORER
Vaccinium dunalianum	LOTUS Database	35616633
Vaccinium macrocarpon	FooDB	PHENOL EXPLORER
Vaccinium myrtillus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium ovalifolium	FooDB	PHENOL EXPLORER
Vaccinium ovatum	FooDB	PHENOL EXPLORER
Vaccinium oxycoccos	FooDB	PHENOL EXPLORER
Vaccinium parvifolium	FooDB	PHENOL EXPLORER
Vaccinium uliginosum	FooDB	PHENOL EXPLORER
Vaccinium vitis-idaea	FooDB	PHENOL EXPLORER
Valeriana amurensis	LOTUS Database	35616633
Valeriana jatamansii	KNApSAcK Database	22123792
Valeriana officinalis	KNApSAcK Database	22123792
Verbena officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Viburnum dilatatum	LOTUS Database	35616633
Viburnum opulus	LOTUS Database	35616633
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vincetoxicum scandens	LOTUS Database	35616633
Viscum album	LOTUS Database	35616633
Viscum coloratum	KNApSAcK Database	22123792
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Woodwardia orientalis	KNApSAcK Database	22123792
Woodwardia prolifera	KNApSAcK Database	22123792
Xanthium strumarium	KNApSAcK Database	22123792
Zea mays	KNApSAcK Database	22123792
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ziziphora clinopodioides	LOTUS Database	35616633
Zostera capricorni	KNApSAcK Database	22123792
Zostera marina	KNApSAcK Database	22123792
Zostera muelleri	KNApSAcK Database	22123792
Zostera noltii	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Inonotus obliquus	KNApSAcK Database	22123792
Monascus pilosus BCRC38072	KNApSAcK Database	22123792
Phellinus igniarius	KNApSAcK Database	22123792

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

caffeic acid (CHEBI:16433 )
Caffeate derivatives (C01197 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	194.00 to 198.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	416.00 to 417.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	54070 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.150	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.67	ALOGPS
logP	1.53	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	17.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001964

DrugBank ID

DB01880

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Caffeic_acid

METLIN ID

Not Available

PubChem Compound

689043

PDB ID

Not Available

ChEBI ID

16433

Good Scents ID

rw1622341

References

General References

Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [PubMed:10706426 ]
Lafay S, Gil-Izquierdo A, Manach C, Morand C, Besson C, Scalbert A: Chlorogenic acid is absorbed in its intact form in the stomach of rats. J Nutr. 2006 May;136(5):1192-7. [PubMed:16614403 ]
Quiles JL, Farquharson AJ, Simpson DK, Grant I, Wahle KW: Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells. Br J Nutr. 2002 Sep;88(3):225-34; discussion 223-4. [PubMed:12207832 ]
Uno J, Tanaka R, Branchini ML, Aoki FH, Yarita K, Sano A, Fukushima K, Mikami Y, Nishimura K, Miyaji M: Atypical Cryptococcus neoformans isolate from an HIV-infected patient in Brazil. Nihon Ishinkin Gakkai Zasshi. 2001;42(3):127-32. [PubMed:11479533 ]
Teng, R. W., et al. (2005). Teng, R. W., et al, Magn. Reson. Chem. 43, 92 (2005). Mag. Reson. Chem..

Showing NP-Card for (E)-caffeic acid (NP0031100)

MOL for NP0031100 ((E)-caffeic acid)

3D MOL for NP0031100 ((E)-caffeic acid)

3D SDF for NP0031100 ((E)-caffeic acid)

3D-SDF for NP0031100 ((E)-caffeic acid)

PDB for NP0031100 ((E)-caffeic acid)

3D PDB for NP0031100 ((E)-caffeic acid)

SMILES for NP0031100 ((E)-caffeic acid)

INCHI for NP0031100 ((E)-caffeic acid)

Structure for NP0031100 ((E)-caffeic acid)

3D Structure for NP0031100 ((E)-caffeic acid)