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Showing metabocard for cis-Caffeic acid (HMDB0003501)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 22:05:42 UTC
Update Date2021-09-07 16:45:35 UTC
HMDB IDHMDB0003501
Secondary Accession Numbers
  • HMDB0006494
  • HMDB03501
  • HMDB06494
Metabolite Identification
Common Namecis-Caffeic acid
DescriptionCaffeic acid, also known as 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 exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in fats and oils and nuts. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g).
Structure
Data?1582752279
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003501 (cis-Caffeic acid)


  Mrv1652307301920012D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -1.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -1.6157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -0.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
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3D MOL for HMDB0003501 (cis-Caffeic acid)

HMDB0003501
     RDKit          3D
cis-Caffeic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.7190    1.8108    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277    1.0116    1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    1.5552    1.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573   -0.3950    0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -1.0672    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -0.6116   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346   -1.2367   -1.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -0.9788   -1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3248   -0.0969   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6372    0.1566   -1.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    0.5286    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463    1.4155    0.9299 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782    0.2469    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    2.0980    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5940   -0.9837    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796   -2.1762    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3307   -1.9397   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9603   -1.4650   -2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678   -0.2654   -2.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    1.6720    0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757    0.7211    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

3D SDF for HMDB0003501 (cis-Caffeic acid)


  Mrv1652307301920012D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -1.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -1.6157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -0.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003501

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)\C=C/C1=CC(O)=C(O)C=C1

> <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-RQOWECAXSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.84830373844111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.5289556166666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.276436861456105

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.143840947271056

> <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

> <JCHEM_TRADITIONAL_IUPAC>
caffeicacid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0003501 (cis-Caffeic acid)

HMDB0003501
     RDKit          3D
cis-Caffeic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.7190    1.8108    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277    1.0116    1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    1.5552    1.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573   -0.3950    0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -1.0672    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -0.6116   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346   -1.2367   -1.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -0.9788   -1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3248   -0.0969   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6372    0.1566   -1.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    0.5286    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463    1.4155    0.9299 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782    0.2469    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    2.0980    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5940   -0.9837    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796   -2.1762    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3307   -1.9397   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9603   -1.4650   -2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678   -0.2654   -2.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    1.6720    0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757    0.7211    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
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PDB for HMDB0003501 (cis-Caffeic acid)

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.197  -2.111   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.443  -3.016   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.197  -0.571   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2   11                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8    9                                                  
CONECT    8    5    7   10                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0003501 (cis-Caffeic acid)

COMPND    HMDB0003501
HETATM    1  O1  UNL     1      -1.719   1.811   0.797  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.628   1.012   1.001  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.801   1.555   1.596  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.657  -0.395   0.717  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.653  -1.067   0.226  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.336  -0.612  -0.116  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.235  -1.237  -1.243  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.519  -0.979  -1.618  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.325  -0.097  -0.917  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.637   0.157  -1.316  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.799   0.529   0.190  1.00  0.00           C  
HETATM   12  O4  UNL     1       2.546   1.415   0.930  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.478   0.247   0.556  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.629   2.098   2.434  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.594  -0.984   0.921  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.880  -2.176   0.057  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.331  -1.940  -1.844  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.960  -1.465  -2.496  1.00  0.00           H  
HETATM   19  H6  UNL     1       4.068  -0.265  -2.105  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.485   1.672   0.743  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.176   0.721   1.487  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7   13
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   11
CONECT   10   19
CONECT   11   12   13   13
CONECT   12   20
CONECT   13   21
END
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SMILES for HMDB0003501 (cis-Caffeic acid)

OC(=O)\C=C/C1=CC(O)=C(O)C=C1
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INCHI for HMDB0003501 (cis-Caffeic acid)

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-
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3,4-Dihydroxycinnamic acidChEBI
CaffeateChEBI
Caffeic acidChEBI
3,4-DihydroxycinnamateGenerator
cis-CaffeateGenerator
3,4-DihydroxybenzeneacrylateHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
Caffeic acid pureHMDB
CaffeicacidHMDB
(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(Z)-Caffeic acidHMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
3-(3,4-Dihydroxyphenyl)propenoic acidHMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzeneHMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzeneHMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzeneHMDB
DHCAHMDB
Isocaffeic acidHMDB
cis-3,4-Dihydroxycinnamic acidHMDB
cis-Caffeic acidHMDB
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Namecaffeicacid
CAS Registry Number4361-87-9
SMILES
OC(=O)\C=C/C1=CC(O)=C(O)C=C1
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 KeyQAIPRVGONGVQAS-RQOWECAXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.35Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available130.714http://allccs.zhulab.cn/database/detail?ID=AllCCS00000431
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP1.53ChemAxon
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+139.55830932474
DeepCCS[M-H]-137.16330932474
DeepCCS[M-2H]-171.30230932474
DeepCCS[M+Na]+145.78230932474
AllCCS[M+H]+138.432859911
AllCCS[M+H-H2O]+134.232859911
AllCCS[M+NH4]+142.432859911
AllCCS[M+Na]+143.532859911
AllCCS[M-H]-135.632859911
AllCCS[M+Na-2H]-136.332859911
AllCCS[M+HCOO]-137.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-Caffeic acidOC(=O)\C=C/C1=CC(O)=C(O)C=C13629.6Standard polar33892256
cis-Caffeic acidOC(=O)\C=C/C1=CC(O)=C(O)C=C11854.3Standard non polar33892256
cis-Caffeic acidOC(=O)\C=C/C1=CC(O)=C(O)C=C11936.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis-Caffeic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C1=CC=C(O)C(O)=C12182.0Semi standard non polar33892256
cis-Caffeic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC(/C=C\C(=O)O)=CC=C1O2036.4Semi standard non polar33892256
cis-Caffeic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O)C=C1O2059.3Semi standard non polar33892256
cis-Caffeic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C(O)=C12100.4Semi standard non polar33892256
cis-Caffeic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)/C=C\C1=CC=C(O)C(O[Si](C)(C)C)=C12086.1Semi standard non polar33892256
cis-Caffeic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O)C=C1O[Si](C)(C)C2090.2Semi standard non polar33892256
cis-Caffeic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12131.4Semi standard non polar33892256
cis-Caffeic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=C(O)C(O)=C12426.0Semi standard non polar33892256
cis-Caffeic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O)=CC=C1O2319.3Semi standard non polar33892256
cis-Caffeic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O)C=C1O2338.2Semi standard non polar33892256
cis-Caffeic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12644.7Semi standard non polar33892256
cis-Caffeic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12606.5Semi standard non polar33892256
cis-Caffeic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2647.2Semi standard non polar33892256
cis-Caffeic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12874.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - cis-Caffeic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9341000000-6dc8d392552b88bd4d8c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-Caffeic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9351000000-50a6f144c73d7ab2794e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-Caffeic acid GC-MS (3 TMS)splash10-014i-2793000000-251334452407128b38bd2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-Caffeic acid GC-EI-TOF (Non-derivatized)splash10-00di-9341000000-6dc8d392552b88bd4d8c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-Caffeic acid GC-EI-TOF (Non-derivatized)splash10-00di-9351000000-50a6f144c73d7ab2794e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-Caffeic acid GC-MS (Non-derivatized)splash10-014i-2793000000-251334452407128b38bd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-Caffeic acid GC-EI-TOF (Non-derivatized)splash10-014i-0692000000-32624fa3a157a1f11cef2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Caffeic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-0900000000-c3283a4b6f6f11b66cfb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Caffeic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00e9-5039000000-d55c6a31e04536d33b582017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Caffeic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Caffeic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-4900000000-3c93f113512b8284301d2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-0900000000-298c46c83441485d1d702012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kr-9800000000-942c1934d3c7c395499e2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-9000000000-e9bdfc2dec7a449ccb112012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-004i-0900000000-b07143eccfcbf1caba0c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-0900000000-8f21d50b78f0d9fde98a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-000i-0900000000-4013461a961ebed6fd992012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0019-2900000000-b41600c20a73cd258d402012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-001r-8900000000-81ea3878c2912bdddf712012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-0900000000-a1680074d0439bcd4c202012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-0900000000-096221135a729c5d6aac2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOFsplash10-0019-0900000000-98893b92962a162b2fb02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-03dr-2900000000-fc2581b0410dd8cb6e712012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-000i-9200000000-0fd7b8f57372dc8172d52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-03dr-2900000000-454a31169c27631fb00c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-0900000000-eb2466a330b617695c802012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ , negative-QTOFsplash10-004i-0900000000-31b407ecba8c8e813fd02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-8f21d50b78f0d9fde98a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-4013461a961ebed6fd992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Caffeic acid LC-ESI-QQ , negative-QTOFsplash10-0019-2900000000-71ad48cc68ef0b7fe30d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Caffeic acid 10V, Positive-QTOFsplash10-03di-0900000000-4d70eb21dfd5dcee33602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Caffeic acid 20V, Positive-QTOFsplash10-01wr-0900000000-eb4ac130dea5eced36c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Caffeic acid 40V, Positive-QTOFsplash10-0100-9800000000-68217b65b3cfbf1771962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Caffeic acid 10V, Negative-QTOFsplash10-004i-0900000000-28ed8e427213908fdd9f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Caffeic acid 20V, Negative-QTOFsplash10-01ti-0900000000-5913f01901b92071e2fc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Caffeic acid 40V, Negative-QTOFsplash10-090u-1900000000-2454d377d14f50d8c9b22017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012666
KNApSAcK IDNot Available
Chemspider ID1266077
KEGG Compound IDC01481
BioCyc IDCPD-8098
BiGG IDNot Available
Wikipedia LinkCaffeic acid
METLIN ID3316
PubChem Compound1549111
PDB IDNot Available
ChEBI ID17395
Food Biomarker OntologyNot Available
VMH ID34DHCINM
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mennen LI, Sapinho D, Ito H, Bertrais S, Galan P, Hercberg S, Scalbert A: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. Br J Nutr. 2006 Jul;96(1):191-8. [PubMed:16870009 ]
  2. Kawaguchi H, Katsuyama Y, Danyao D, Kahar P, Nakamura-Tsuruta S, Teramura H, Wakai K, Yoshihara K, Minami H, Ogino C, Ohnishi Y, Kondo A: Caffeic acid production by simultaneous saccharification and fermentation of kraft pulp using recombinant Escherichia coli. Appl Microbiol Biotechnol. 2017 Jul;101(13):5279-5290. doi: 10.1007/s00253-017-8270-0. Epub 2017 Apr 10. [PubMed:28396925 ]

Enzymes

Enzyme Details
1. Tyrosinase
General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
Enzyme Details
2. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
cis-Caffeic acid → Ferulic aciddetails
Enzyme Details
3. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
cis-Caffeic acid → 6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
cis-Caffeic acid → 6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
cis-Caffeic acid → 6-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Enzyme Details
4. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
cis-Caffeic acid → Caffeic acid 3-O-sulfatedetails