Hmdb loader

Showing metabocard for p-Hydroxymandelic acid (HMDB0000822)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:13 UTC
HMDB IDHMDB0000822
Secondary Accession Numbers
  • HMDB00822
Metabolite Identification
Common Namep-Hydroxymandelic acid
Descriptionp-Hydroxymandelic acid, also known as 4-hydroxymandelate or 4-hydroxyphenylglycolate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. p-Hydroxymandelic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make p-hydroxymandelic acid a potential biomarker for the consumption of these foods. p-Hydroxymandelic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on p-Hydroxymandelic acid.
Structure
Data?1676999712
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000822 (p-Hydroxymandelic acid)


  Mrv1652305231920442D          

 12 12  0  0  1  0            999 V2000
    0.7145   -0.4125    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    0.4125    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    0.4125    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
    2.1433   -0.4125    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
    2.1433    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  2  1  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  0  0  0  0
  5 12  1  0  0  0  0
  2  6  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000822 (p-Hydroxymandelic acid)

HMDB0000822
     RDKit          3D
p-Hydroxymandelic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.1668   -0.6077   -1.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.6047   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6113   -1.8016    0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105    0.5582    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    1.5697   -0.9041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    0.3204    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801   -0.9420   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -1.1635   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019   -0.0933   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -0.2783   -0.0501 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0110    1.2041    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6397    1.3871    0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4516   -2.0223    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189    0.8678    1.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263    2.4010   -0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379   -1.8366   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0365   -2.1941   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406   -1.2270   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881    2.0466    0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    2.4163    0.0513 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
  4  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  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for HMDB0000822 (p-Hydroxymandelic acid)


  Mrv1652305231920442D          

 12 12  0  0  1  0            999 V2000
    0.7145   -0.4125    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    0.4125    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    0.4125    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
    2.1433   -0.4125    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
    2.1433    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  2  1  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  0  0  0  0
  5 12  1  0  0  0  0
  2  6  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000822

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)

> <INCHI_KEY>
YHXHKYRQLYQUIH-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.644347996836352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(4-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
0.5922703229999999

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.475213707677849

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3028147671822787

> <JCHEM_PKA_STRONGEST_BASIC>
-4.105652938089659

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
40.6847

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxymandelic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000822 (p-Hydroxymandelic acid)

HMDB0000822
     RDKit          3D
p-Hydroxymandelic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.1668   -0.6077   -1.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.6047   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6113   -1.8016    0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105    0.5582    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    1.5697   -0.9041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    0.3204    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801   -0.9420   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -1.1635   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019   -0.0933   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -0.2783   -0.0501 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0110    1.2041    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6397    1.3871    0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4516   -2.0223    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189    0.8678    1.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263    2.4010   -0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379   -1.8366   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0365   -2.1941   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406   -1.2270   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881    2.0466    0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    2.4163    0.0513 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
  4  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  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

PDB for HMDB0000822 (p-Hydroxymandelic acid)

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    8    2    3                                                  
CONECT    2    1    6                                                       
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   12    6                                                  
CONECT    6    2    5                                                       
CONECT    7    8    9   10                                                  
CONECT    8    1    7   11                                                  
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for HMDB0000822 (p-Hydroxymandelic acid)

COMPND    HMDB0000822
HETATM    1  O1  UNL     1      -3.167  -0.608  -1.486  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.502  -0.605  -0.393  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.611  -1.802   0.320  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.711   0.558   0.046  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.913   1.570  -0.904  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.234   0.320   0.020  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.280  -0.942  -0.010  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.638  -1.164  -0.034  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.502  -0.093  -0.027  1.00  0.00           C  
HETATM   10  O4  UNL     1       3.885  -0.278  -0.050  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.011   1.204   0.004  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.640   1.387   0.027  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.452  -2.022   0.834  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.019   0.868   1.061  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.226   2.401  -0.451  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.338  -1.837  -0.019  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.036  -2.194  -0.058  1.00  0.00           H  
HETATM   18  H6  UNL     1       4.241  -1.227  -0.072  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.688   2.047   0.009  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.252   2.416   0.051  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    6   14
CONECT    5   15
CONECT    6    7    7   12
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   11
CONECT   10   18
CONECT   11   12   12   19
CONECT   12   20
END
Download

SMILES for HMDB0000822 (p-Hydroxymandelic acid)

OC(C(O)=O)C1=CC=C(O)C=C1
Download

INCHI for HMDB0000822 (p-Hydroxymandelic acid)

InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-Hydroxyphenylglycolic acidChEBI
4-HydroxyphenylglycolateGenerator
4-HydroxymandelateGenerator
p-HydroxymandelateGenerator
(+/-)-alpha,4-dihydroxy-benzeneacetateHMDB
(+/-)-alpha,4-dihydroxy-benzeneacetic acidHMDB
(R)-4-HydroxymandelateHMDB
(RS)-p-HydroxymandelateHMDB
(RS)-p-Hydroxymandelic acidHMDB
(S)-4-HydroxymandelateHMDB
2-(4-Hydroxyphenyl)-2-hydroxyacetateHMDB
2-(4-Hydroxyphenyl)-2-hydroxyacetic acidHMDB
3-Dimethylallyl-4-hydroxymandelateHMDB
3-Dimethylallyl-4-hydroxymandelic acidHMDB
4-Hydroxy-DL-mandelateHMDB
4-Hydroxy-DL-mandelic acidHMDB
alpha,4-Dihydroxy-benzeneacetateHMDB
alpha,4-Dihydroxy-benzeneacetic acidHMDB
alpha,4-DihydroxybenzeneacetateHMDB
alpha,4-Dihydroxybenzeneacetic acidHMDB
D-4-HydroxymandelateHMDB
D-p-HydroxymandelateHMDB
delta-4-HydroxymandelateHMDB
delta-p-HydroxymandelateHMDB
DL-4-HydroxymandelateHMDB
DL-4-Hydroxymandelic acidHMDB
DL-p-HydroxymandelateHMDB
DL-p-Hydroxymandelic acidHMDB
DL-p-HydroxyphenylglycolateHMDB
DL-p-Hydroxyphenylglycolic acidHMDB
Hydroxy(4-hydroxyphenyl)acetateHMDB
Hydroxy(4-hydroxyphenyl)acetic acidHMDB
L-4-HydroxymandelateHMDB
L-p-HydroxymandelateHMDB
p-Hydroxy-mandelateHMDB
p-Hydroxy-mandelic acidHMDB
p-HydroxyphenylglycolateHMDB
p-Hydroxyphenylglycolic acidHMDB
Para-hydroxymandelic acidHMDB
4-Hydroxymandelic acid, (D)-isomerHMDB
Pisolithin bHMDB
2-Hydroxy-2-(4'-hydroxyphenyl)acetic acidHMDB
2-Hydroxy-2-(4-hydroxyphenyl)acetic acidHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-2-(4-hydroxyphenyl)acetic acid
Traditional Name4-hydroxymandelic acid
CAS Registry Number1198-84-1
SMILES
OC(C(O)=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
InChI KeyYHXHKYRQLYQUIH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point103 - 106 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.69 g/LALOGPS
logP0.86ALOGPS
logP0.59ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.68 m³·mol⁻¹ChemAxon
Polarizability15.64 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
DarkChem[M+H]+137.54331661259
DarkChem[M-H]-131.66231661259
AllCCS[M+H]+136.84532859911
AllCCS[M-H]-132.56432859911
DeepCCS[M+H]+132.07530932474
DeepCCS[M-H]-129.2530932474
DeepCCS[M-2H]-165.3930932474
DeepCCS[M+Na]+140.35830932474
AllCCS[M+H]+136.832859911
AllCCS[M+H-H2O]+132.532859911
AllCCS[M+NH4]+140.932859911
AllCCS[M+Na]+142.132859911
AllCCS[M-H]-132.632859911
AllCCS[M+Na-2H]-133.632859911
AllCCS[M+HCOO]-134.832859911

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. Predicted by Afia on May 17, 2022.2.11 minutes32390414
Predicted by Siyang on May 30, 20229.2475 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.96 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid112.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid917.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid291.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid85.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid169.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid62.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid262.8 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 Acid269.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)360.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid604.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid140.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid858.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid191.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid206.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate543.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA307.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water214.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-Hydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C=C13474.2Standard polar33892256
p-Hydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C=C11700.9Standard non polar33892256
p-Hydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C=C11655.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Hydroxymandelic acid,1TMS,isomer #1C[Si](C)(C)OC(C(=O)O)C1=CC=C(O)C=C11792.1Semi standard non polar33892256
p-Hydroxymandelic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C=C11735.2Semi standard non polar33892256
p-Hydroxymandelic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C11720.5Semi standard non polar33892256
p-Hydroxymandelic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O)C=C11810.3Semi standard non polar33892256
p-Hydroxymandelic acid,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C)C(=O)O)C=C11740.7Semi standard non polar33892256
p-Hydroxymandelic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C)C=C11732.9Semi standard non polar33892256
p-Hydroxymandelic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C11779.9Semi standard non polar33892256
p-Hydroxymandelic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C(=O)O)C1=CC=C(O)C=C12047.1Semi standard non polar33892256
p-Hydroxymandelic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C=C11992.6Semi standard non polar33892256
p-Hydroxymandelic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C12005.0Semi standard non polar33892256
p-Hydroxymandelic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C12265.3Semi standard non polar33892256
p-Hydroxymandelic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C12259.0Semi standard non polar33892256
p-Hydroxymandelic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12235.6Semi standard non polar33892256
p-Hydroxymandelic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12424.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - p-Hydroxymandelic acid GC-EI-TOF (Non-derivatized)splash10-014i-1970000000-156d51ef8c0ad0f76d642017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Hydroxymandelic acid GC-EI-TOF (Non-derivatized)splash10-014i-1970000000-156d51ef8c0ad0f76d642018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-8900000000-b062f43216386832dded2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1091000000-70622b0e5331b2fe290f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Hydroxymandelic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxymandelic acid 10V, Negative-QTOFsplash10-014i-0900000000-34b31ac9e80ec28f0bbc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxymandelic acid 40V, Negative-QTOFsplash10-00dl-4900000000-776e3b6ee256d0fe5cb42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxymandelic acid 20V, Negative-QTOFsplash10-00di-4900000000-9dd6f152de533ac938a22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxymandelic acid 40V, Positive-QTOFsplash10-014i-9000000000-415c5d4c2ea88934e2c42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxymandelic acid 35V, Negative-QTOFsplash10-00di-0900000000-9c790106a25e9dd43e942021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxymandelic acid 20V, Positive-QTOFsplash10-0006-9300000000-73afdd4e3b6cbc4726e92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Hydroxymandelic acid 10V, Positive-QTOFsplash10-014i-4900000000-48da404afde1f15d26912021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 10V, Positive-QTOFsplash10-0v4i-0900000000-da456e31e91f9a9b7c342015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 20V, Positive-QTOFsplash10-00di-1900000000-bb2667f5c8ef34847d412015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 40V, Positive-QTOFsplash10-00fv-9600000000-c7c25ea1fa9244b02d822015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 10V, Negative-QTOFsplash10-01b9-0900000000-0853088e78547b0023942015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 20V, Negative-QTOFsplash10-00r7-4900000000-4fd0952fc81ec79b040f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 40V, Negative-QTOFsplash10-0006-9200000000-6c7af63bb32592f280fa2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 10V, Positive-QTOFsplash10-0v4i-0900000000-bc65c2527a8df7d8147a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 20V, Positive-QTOFsplash10-0pba-4900000000-9f3e7769f03e19541e952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 40V, Positive-QTOFsplash10-014i-9000000000-3bd2d0f928f8e1b0e0b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 10V, Negative-QTOFsplash10-014i-4900000000-a948bbe144908fb34a342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 20V, Negative-QTOFsplash10-0596-5900000000-a99429838637eb5a45ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Hydroxymandelic acid 40V, Negative-QTOFsplash10-0006-9100000000-a202d17e840c1184fce52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Retina
  • Vitreous humor
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified1.844 (0.511-6.0959) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified4.1 (0.1-4.9) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified3.7 (1.3-6.8) umol/mmol creatinineChildren (1-13 years old)Both
Normal		 details
UrineDetected and Quantified4.3 (1.4-10.0) umol/mmol creatinineChildren (1-13 years old)Both
Normal		 details
UrineDetected and Quantified0.91-1.7 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.98-1.5 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 IDFDB022267
KNApSAcK IDNot Available
Chemspider ID321
KEGG Compound IDC11527
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxymandelic acid
METLIN ID5785
PubChem Compound328
PDB IDNot Available
ChEBI ID16388
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWang, Bing; Zhang, Guofeng. Synthesis and purity determination of p-hydroxymandelic acid. Qingdao Daxue Xuebao, Gongcheng Jishuban (1999), 14(1), 14-16.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]
  3. Crowley JR, Couch MW, Williams CM, Threatte RM, Fregly MJ: Normal excretion of m-hydroxymandelic acid in hypertensive patients. Clin Chim Acta. 1981 Jan 22;109(2):125-31. [PubMed:7471493 ]
  4. Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738 ]
  5. Couch MW, Greer DM, Williams CM: Excretion of octopamine metabolites in neuroblastoma. Clin Chim Acta. 1986 Jul 15;158(1):109-14. [PubMed:3091293 ]
  6. Niwa T, Ohki T, Maeda K, Saito A, Ohta K, Kobayashi K: A gas chromatographic-mass spectrometric assay for nine hydroxyphenolic acids in uremic serum. Clin Chim Acta. 1979 Sep 3;96(3):247-54. [PubMed:487594 ]
  7. Arai K, Jin D, Kusu F, Takamura K: Determination of p-hydroxymandelic acid enantiomers in urine by high-performance liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1997 Jun;15(9-10):1509-14. [PubMed:9226583 ]