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Showing metabocard for 3-(2-Hydroxyphenyl)propanoic acid (HMDB0033752)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:30:47 UTC
Update Date2023-02-21 17:23:34 UTC
HMDB IDHMDB0033752
Secondary Accession Numbers
  • HMDB33752
Metabolite Identification
Common Name3-(2-Hydroxyphenyl)propanoic acid
Description3-(2-Hydroxyphenyl)propanoic acid, also known as melilotic acid or melilotate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(2-Hydroxyphenyl)propanoic acid exists in all living organisms, ranging from bacteria to humans. 3-(2-Hydroxyphenyl)propanoic acid has been detected, but not quantified in, several different foods, such as bilberries (Vaccinium myrtillus), chinese cinnamons (Cinnamomum aromaticum), herbs and spices, pulses, and red beetroots (Beta vulgaris var. rubra). This could make 3-(2-hydroxyphenyl)propanoic acid a potential biomarker for the consumption of these foods. 3-(2-Hydroxyphenyl)propanoic 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. Based on a literature review a significant number of articles have been published on 3-(2-Hydroxyphenyl)propanoic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033752 (3-(2-Hydroxyphenyl)propanoic acid)

  Mrv0541 05061307202D          

 12 12  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    1.4289    0.8250    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    0.8250    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
   -2.1434    1.2375    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
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
M  END
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3D MOL for HMDB0033752 (3-(2-Hydroxyphenyl)propanoic acid)

HMDB0033752
     RDKit          3D
3-(2-Hydroxyphenyl)propanoic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.3316   -0.5121    1.5120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354    0.0192    0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    1.1922    1.2373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -0.6761   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -0.0248   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    0.1407   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    1.3510   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9527    1.4994    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7621    0.4219    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3288   -0.8114    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1049   -0.9639   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -2.2149   -0.9093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271    2.0636    0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303   -0.6866   -1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8685   -1.7361   -0.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8488   -0.6285   -2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    0.9722   -1.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917    2.2254   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704    2.4620    0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305    0.5449    1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950   -1.6473    0.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144   -2.9908   -0.7767 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
M  END
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3D SDF for HMDB0033752 (3-(2-Hydroxyphenyl)propanoic acid)

  Mrv0541 05061307202D          

 12 12  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    1.4289    0.8250    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    0.8250    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
   -2.1434    1.2375    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
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033752

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCC1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-4,10H,5-6H2,(H,11,12)

> <INCHI_KEY>
CJBDUOMQLFKVQC-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.770918778532902

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.7519974486666663

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.373582561278479

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216609444542158

> <JCHEM_PKA_STRONGEST_BASIC>
-6.002420957773741

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
43.947500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melilotic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0033752 (3-(2-Hydroxyphenyl)propanoic acid)

HMDB0033752
     RDKit          3D
3-(2-Hydroxyphenyl)propanoic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.3316   -0.5121    1.5120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354    0.0192    0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    1.1922    1.2373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -0.6761   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -0.0248   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    0.1407   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    1.3510   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9527    1.4994    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7621    0.4219    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3288   -0.8114    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1049   -0.9639   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -2.2149   -0.9093 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271    2.0636    0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303   -0.6866   -1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8685   -1.7361   -0.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8488   -0.6285   -2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    0.9722   -1.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917    2.2254   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704    2.4620    0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7305    0.5449    1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950   -1.6473    0.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144   -2.9908   -0.7767 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0033752 (3-(2-Hydroxyphenyl)propanoic acid)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    3    5    8                                                  
CONECT    8    4    7   10                                                  
CONECT    9    6   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0033752 (3-(2-Hydroxyphenyl)propanoic acid)

COMPND    HMDB0033752
HETATM    1  O1  UNL     1       3.332  -0.512   1.512  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.435   0.019   0.766  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.903   1.192   1.237  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.095  -0.676  -0.473  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.048  -0.025  -1.311  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.265   0.141  -0.646  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.717   1.351  -0.187  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.953   1.499   0.433  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.762   0.422   0.601  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.329  -0.811   0.146  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.105  -0.964  -0.468  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.707  -2.215  -0.909  1.00  0.00           O  
HETATM   13  H1  UNL     1       2.327   2.064   0.959  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.030  -0.687  -1.109  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.869  -1.736  -0.257  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.849  -0.628  -2.241  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.352   0.972  -1.698  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.092   2.225  -0.313  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.270   2.462   0.778  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.731   0.545   1.087  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.995  -1.647   0.296  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.314  -2.991  -0.777  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7    7   11
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   10   20
CONECT   10   11   11   21
CONECT   11   12
CONECT   12   22
END
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SMILES for HMDB0033752 (3-(2-Hydroxyphenyl)propanoic acid)

OC(=O)CCC1=CC=CC=C1O
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INCHI for HMDB0033752 (3-(2-Hydroxyphenyl)propanoic acid)

InChI=1S/C9H10O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-4,10H,5-6H2,(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-(2-hydroxyphenyl)propanoic acid
Traditional Namemelilotic acid
CAS Registry Number495-78-3
SMILES
OC(=O)CCC1=CC=CC=C1O
InChI Identifier
InChI=1S/C9H10O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-4,10H,5-6H2,(H,11,12)
InChI KeyCJBDUOMQLFKVQC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point82 - 83 °CNot Available
Boiling Point335.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility17370 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.100 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available134.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00002154
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011887
KNApSAcK IDC00002756
Chemspider ID850
KEGG Compound IDC01198
BioCyc IDMELILOTATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound873
PDB IDNot Available
ChEBI ID16104
Food Biomarker OntologyNot Available
VMH IDMELT
MarkerDB IDNot Available
Good Scents IDrw1185661
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. 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
3-(2-Hydroxyphenyl)propanoic acid → 6-[2-(2-carboxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(2-Hydroxyphenyl)propanoic acid → 3,4,5-trihydroxy-6-{[3-(2-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails