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 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 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 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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.3 (1.4-10.0) umol/mmol creatinineChildren (1-13 years old)Both
Normal		 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 ]