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Showing metabocard for 3,5-Dihydroxycinnamic acid (HMDB0032131)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:48:02 UTC
Update Date2023-02-21 17:21:38 UTC
HMDB IDHMDB0032131
Secondary Accession Numbers
  • HMDB0125527
  • HMDB32131
Metabolite Identification
Common Name3,5-Dihydroxycinnamic acid
Description3,5-Dihydroxycinnamic acid (DHA) (CAS: 28374-93-8) is found in fruits. It can be isolated from peach buds. BioTransformer predicts that 3,5-dihydroxycinnamic acid is a product of 3,​4,​5-​trihydroxycinnamic acid metabolism via a -4p-dehydroxylation-of-substituted-benzene reaction occurring in human gut microbiota and catalyzed by a dehydroxylase enzyme (PMID: 30612223 ). 3,5-Dihydroxycinnamic acid is an alkylresorcinol metabolite. It is a potential urinary biomarker of whole grain intake (PMID: 28444884 ).
Structure
Data?1677000098
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032131 (3,5-Dihydroxycinnamic acid)


  Mrv1652308071918062D          

 13 13  0  0  0  0            999 V2000
    1.7860    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    0.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0715    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -2.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  4  1  0  0  0  0
  6 12  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
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3D MOL for HMDB0032131 (3,5-Dihydroxycinnamic acid)

HMDB0032131
     RDKit          3D
3,5-Dihydroxycinnamic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    4.0566   -2.1991   -0.6722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.1938   -0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2452   -0.2394    0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0416   -1.0813   -0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680   -0.0305    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319    0.1523    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -0.7172   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -0.5037   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546   -1.4428   -1.3750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    0.6354   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8549    1.5214    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116    2.6676    1.1244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5026    1.2907    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2200   -0.1478    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5355   -1.8574   -0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0883    0.6877    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -1.6127   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9548   -1.3557   -1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673    0.8061   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225    2.5985    2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    2.0216    1.1549 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  1  0
  8 10  2  0
 10 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
  9 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
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3D SDF for HMDB0032131 (3,5-Dihydroxycinnamic acid)


  Mrv1652308071918062D          

 13 13  0  0  0  0            999 V2000
    1.7860    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    0.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0715    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -2.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  4  1  0  0  0  0
  6 12  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032131

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h1-5,10-11H,(H,12,13)/b2-1+

> <INCHI_KEY>
MFFCZSWTQMCKFP-OWOJBTEDSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.159

> <EXACT_MASS>
180.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.360742979074175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.5289556166666665

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.167249502959805

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6346470217964715

> <JCHEM_PKA_STRONGEST_BASIC>
-5.6785511467900855

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
47.021699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0032131 (3,5-Dihydroxycinnamic acid)

HMDB0032131
     RDKit          3D
3,5-Dihydroxycinnamic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    4.0566   -2.1991   -0.6722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.1938   -0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2452   -0.2394    0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0416   -1.0813   -0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680   -0.0305    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319    0.1523    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -0.7172   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -0.5037   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546   -1.4428   -1.3750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    0.6354   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8549    1.5214    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116    2.6676    1.1244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5026    1.2907    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2200   -0.1478    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5355   -1.8574   -0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0883    0.6877    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -1.6127   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9548   -1.3557   -1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673    0.8061   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225    2.5985    2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    2.0216    1.1549 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  1  0
  8 10  2  0
 10 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
  9 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
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PDB for HMDB0032131 (3,5-Dihydroxycinnamic acid)

HEADER    PROTEIN                                 07-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-AUG-19         0                                  
HETATM    1  C   UNK     0       3.334   0.772   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.668   0.003   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.334   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.000   0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.666   0.771   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.668   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.001  -3.849   0.000  0.00  0.00           O+0
CONECT    1    2    3   10                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5    9   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    4                                                       
CONECT   10    1   11                                                       
CONECT   11   10    4                                                       
CONECT   12    6                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0032131 (3,5-Dihydroxycinnamic acid)

COMPND    HMDB0032131
HETATM    1  O1  UNL     1       4.057  -2.199  -0.672  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.502  -1.194  -0.173  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.245  -0.239   0.508  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.042  -1.081  -0.346  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.468  -0.030   0.176  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.032   0.152   0.049  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.813  -0.717  -0.599  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.191  -0.504  -0.699  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.955  -1.443  -1.375  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.693   0.635  -0.113  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.855   1.521   0.543  1.00  0.00           C  
HETATM   12  O4  UNL     1      -2.412   2.668   1.124  1.00  0.00           O  
HETATM   13  C9  UNL     1      -0.503   1.291   0.629  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.220  -0.148   0.249  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.536  -1.857  -0.884  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.088   0.688   0.699  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.415  -1.613  -1.059  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.955  -1.356  -1.487  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.767   0.806  -0.189  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.723   2.599   2.086  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.092   2.022   1.155  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   10   10
CONECT    9   18
CONECT   10   11   19
CONECT   11   12   13   13
CONECT   12   20
CONECT   13   21
END
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SMILES for HMDB0032131 (3,5-Dihydroxycinnamic acid)

OC(=O)\C=C\C1=CC(O)=CC(O)=C1
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INCHI for HMDB0032131 (3,5-Dihydroxycinnamic acid)

InChI=1S/C9H8O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h1-5,10-11H,(H,12,13)/b2-1+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3,5-DihydroxycinnamateGenerator
(2E)-3-(3,5-Dihydroxyphenyl)prop-2-enoateHMDB
(2E)-3-(3,5-Dihydroxyphenyl)-2-propenoic acidHMDB
(e)-3-(3,5-Dihydroxyphenyl)acrylic acidHMDB
3-(3,5-Dihydroxyphenyl)-2-propenoic acidHMDB
3-(3,5-Dihydroxyphenyl)prop-2-enoic acidHMDB
DHCAHMDB
3,5-Dihydroxycinnamic acidHMDB
Chemical FormulaC9H8O4
Average Molecular Weight180.159
Monoisotopic Molecular Weight180.042258738
IUPAC Name(2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid
Traditional Name(2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid
CAS Registry Number127791-54-2
SMILES
OC(=O)\C=C\C1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h1-5,10-11H,(H,12,13)/b2-1+
InChI KeyMFFCZSWTQMCKFP-OWOJBTEDSA-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
  • Styrene
  • Resorcinol
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point245 - 246 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.45 g/LALOGPS
logP1.47ALOGPS
logP1.53ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability17.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+136.9130932474
DeepCCS[M-H]-134.51530932474
DeepCCS[M-2H]-169.06830932474
DeepCCS[M+Na]+143.52730932474
AllCCS[M+H]+138.032859911
AllCCS[M+H-H2O]+133.732859911
AllCCS[M+NH4]+141.932859911
AllCCS[M+Na]+143.132859911
AllCCS[M-H]-134.132859911
AllCCS[M+Na-2H]-134.832859911
AllCCS[M+HCOO]-135.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 3.1 minutes32390414
Predicted by Siyang on May 30, 20229.7163 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.54 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid64.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1045.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid294.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid87.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid163.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid81.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid346.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid258.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)360.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid680.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid236.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid953.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid184.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid231.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate561.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA272.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water156.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,5-Dihydroxycinnamic acidOC(=O)\C=C\C1=CC(O)=CC(O)=C13863.7Standard polar33892256
3,5-Dihydroxycinnamic acidOC(=O)\C=C\C1=CC(O)=CC(O)=C11914.2Standard non polar33892256
3,5-Dihydroxycinnamic acidOC(=O)\C=C\C1=CC(O)=CC(O)=C12068.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,5-Dihydroxycinnamic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC(O)=CC(O)=C12126.2Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC(/C=C/C(=O)O)=C12099.2Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC(O)=CC(O[Si](C)(C)C)=C12160.9Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,2TMS,isomer #2C[Si](C)(C)OC1=CC(/C=C/C(=O)O)=CC(O[Si](C)(C)C)=C12123.2Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C12142.4Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC(O)=CC(O)=C12367.1Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C(=O)O)=C12355.7Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C12685.5Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C12648.1Semi standard non polar33892256
3,5-Dihydroxycinnamic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C12887.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dihydroxycinnamic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00di-7049000000-ce53965ec25e00b0ce9b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dihydroxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-d1d04d41b41d04d6945f2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dihydroxycinnamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dihydroxycinnamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 10V, Positive-QTOFsplash10-03di-0900000000-c1e096bdfab218e1788c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 20V, Positive-QTOFsplash10-03dr-0900000000-3929e25bd302c5c206fc2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 40V, Positive-QTOFsplash10-00kr-6900000000-c72175f2a9a913be8c642019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 10V, Negative-QTOFsplash10-004i-0900000000-9ece1386317b857876d92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 20V, Negative-QTOFsplash10-01ti-0900000000-d7db5e5f87f2edb1249b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 40V, Negative-QTOFsplash10-08gu-1900000000-0e0d1ce16d754f6cbdef2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 10V, Negative-QTOFsplash10-004r-0900000000-7f3073eac44d6b5f62422021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 20V, Negative-QTOFsplash10-000i-0900000000-98a352782abfdde7d3ea2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 40V, Negative-QTOFsplash10-000x-9600000000-cb090793e1bcf572facb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 10V, Positive-QTOFsplash10-03di-0900000000-3102fe8873d972cc4dd92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 20V, Positive-QTOFsplash10-01p9-1900000000-462d2391c15d8c9c830a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 40V, Positive-QTOFsplash10-0ftu-9700000000-a51ee75ddeef062d742e2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031414
KNApSAcK IDNot Available
Chemspider ID4947733
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3,5-Dihydroxycinnamic acid
METLIN IDNot Available
PubChem Compound6443769
PDB IDNot Available
ChEBI ID189723
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]
  2. Wierzbicka R, Zamaratskaia G, Kamal-Eldin A, Landberg R: Novel urinary alkylresorcinol metabolites as biomarkers of whole grain intake in free-living Swedish adults. Mol Nutr Food Res. 2017 Jul;61(7). doi: 10.1002/mnfr.201700015. Epub 2017 Jun 14. [PubMed:28444884 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .