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Showing metabocard for 3-Hydroxymandelic acid (HMDB0000750)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:08 UTC
HMDB IDHMDB0000750
Secondary Accession Numbers
  • HMDB00750
Metabolite Identification
Common Name3-Hydroxymandelic acid
Description3-Hydroxymandelic acid, also known as m-hydroxymandelate or MHMA, is a 2-hydroxy monocarboxylic acid. 3-Hydroxymandelic acid is the dehydroxylated (positions 2 and 3’) derivative of phenylacetic acid. It is a white crystalline solid that is soluble in water and polar organic solvents. It derives from a mandelic acid. Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. Mandelate dehydrogenase is yet another enzyme on this pathway. Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated. Derivatives of mandelic acid, such as 3-hydroxymandelic acid, are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase.
Structure
Data?1676999708
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000750 (3-Hydroxymandelic acid)

<string xmlns="http://www.chemspider.com/">86957
  Mrv1652304222010582D          

 12 12  0  0  1  0            999 V2000
    3.0179    1.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -1.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    2.0113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1613    0.7738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -0.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    0.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    1.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3 12  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000750 (3-Hydroxymandelic acid)

HMDB0000750
     RDKit          3D
3-Hydroxymandelic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.0542   -1.4537    1.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.8883    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -1.6012   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177    0.4456    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    1.0010   -1.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396    0.3920    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304    1.5768   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.5244   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025    0.3660   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8438   -0.7727    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -1.9856    0.4118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -0.7621    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9508   -1.9163   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9259    1.1488    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    1.3719   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    2.5017   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345    2.4460   -0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    0.3197   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -2.0242    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -1.6899    0.5367 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
 10 11  1  0
 10 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
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for HMDB0000750 (3-Hydroxymandelic acid)

<string xmlns="http://www.chemspider.com/">86957
  Mrv1652304222010582D          

 12 12  0  0  1  0            999 V2000
    3.0179    1.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -1.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    2.0113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1613    0.7738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -0.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    0.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    1.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3 12  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000750

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
OLSDAJRAVOVKLG-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.549898712046303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(3-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.5922703229999999

> <ALOGPS_LOGS>
-1.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.370825435875659

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.303530000093164

> <JCHEM_PKA_STRONGEST_BASIC>
-4.132531240571596

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
40.6847

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
MHMA

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000750 (3-Hydroxymandelic acid)

HMDB0000750
     RDKit          3D
3-Hydroxymandelic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.0542   -1.4537    1.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.8883    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -1.6012   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177    0.4456    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    1.0010   -1.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396    0.3920    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304    1.5768   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.5244   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025    0.3660   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8438   -0.7727    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -1.9856    0.4118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -0.7621    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9508   -1.9163   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9259    1.1488    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    1.3719   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    2.5017   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345    2.4460   -0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    0.3197   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -2.0242    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -1.6899    0.5367 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
 10 11  1  0
 10 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
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

PDB for HMDB0000750 (3-Hydroxymandelic acid)

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">86957  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0       5.633   2.214   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.300  -3.176   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.301   3.754   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.634   1.444   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.967  -0.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.967   1.444   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.633  -0.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.301  -0.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.633  -2.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.301  -2.406   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.967  -3.176   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.301   2.214   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    6    7    8                                                  
CONECT    6    1    5   12                                                  
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    2    7   11                                                  
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    3    4    6                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0000750 (3-Hydroxymandelic acid)

COMPND    HMDB0000750
HETATM    1  O1  UNL     1      -2.054  -1.454   1.499  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.263  -0.888   0.393  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.015  -1.601  -0.533  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.718   0.446   0.157  1.00  0.00           C  
HETATM    5  O3  UNL     1      -2.181   1.001  -1.050  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.240   0.392   0.066  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.430   1.577  -0.269  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.799   1.524  -0.367  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.503   0.366  -0.148  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.844  -0.773   0.175  1.00  0.00           C  
HETATM   11  O4  UNL     1       2.481  -1.986   0.412  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.463  -0.762   0.283  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.951  -1.916  -0.324  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.926   1.149   1.000  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.405   1.372  -1.523  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.116   2.502  -0.443  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.335   2.446  -0.629  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.590   0.320  -0.225  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.472  -2.024   0.341  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.047  -1.690   0.537  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   18
CONECT   10   11   12   12
CONECT   11   19
CONECT   12   20
END
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SMILES for HMDB0000750 (3-Hydroxymandelic acid)

OC(C(O)=O)C1=CC(O)=CC=C1
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INCHI for HMDB0000750 (3-Hydroxymandelic acid)

InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Hydroxy-2-(3-hydroxyphenyl)acetic acidChEBI
m-Hydroxymandelic acidChEBI
2-Hydroxy-2-(3-hydroxyphenyl)acetateGenerator
2-Hydroxy-2-(3-hydroxyphenyl)ethanoateGenerator
m-HydroxymandelateGenerator
3-HydroxymandelateGenerator
3-Hydroxyphenylglycolic acidHMDB
alpha,3-Dihydroxybenzeneacetic acidHMDB
DL-3-HydroxymandelateHMDB
DL-3-Hydroxymandelic acidHMDB
DL-Hydroxy(m-hydroxyphenyl)acetic acidHMDB
Hydroxy(3-hydroxyphenyl)acetic acidHMDB
m-Hydroxy-(6ci,7ci,8ci)mandelateHMDB
m-Hydroxy-(6ci,7ci,8ci)mandelic acidHMDB
Meta-hydroxymandelic acidHMDB
MHMAHMDB
2-Hydroxy-2-(3'-hydroxyphenyl)acetic acidHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-2-(3-hydroxyphenyl)acetic acid
Traditional NameMHMA
CAS Registry Number17119-15-2
SMILES
OC(C(O)=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
InChI KeyOLSDAJRAVOVKLG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility31 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP0.89ALOGPS
logP0.59ChemAxon
logS-1.2ALOGPS
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
Polarizability15.55 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]+136.81331661259
DarkChem[M-H]-131.36431661259
AllCCS[M+H]+136.62532859911
AllCCS[M-H]-131.3132859911
DeepCCS[M+H]+131.03230932474
DeepCCS[M-H]-128.44730932474
DeepCCS[M-2H]-164.21530932474
DeepCCS[M+Na]+139.27830932474
AllCCS[M+H]+136.632859911
AllCCS[M+H-H2O]+132.232859911
AllCCS[M+NH4]+140.732859911
AllCCS[M+Na]+141.932859911
AllCCS[M-H]-131.332859911
AllCCS[M+Na-2H]-132.332859911
AllCCS[M+HCOO]-133.532859911

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, 2022.2.42 minutes32390414
Predicted by Siyang on May 30, 20229.3562 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.04 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid112.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid958.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid294.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid86.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid171.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid69.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid271.5 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 Acid274.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)339.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid621.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid150.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid858.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid194.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid211.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate512.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA309.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water201.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxymandelic acidOC(C(O)=O)C1=CC(O)=CC=C13401.0Standard polar33892256
3-Hydroxymandelic acidOC(C(O)=O)C1=CC(O)=CC=C11690.0Standard non polar33892256
3-Hydroxymandelic acidOC(C(O)=O)C1=CC(O)=CC=C11662.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxymandelic acid,1TMS,isomer #1C[Si](C)(C)OC(C(=O)O)C1=CC=CC(O)=C11734.8Semi standard non polar33892256
3-Hydroxymandelic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(O)C1=CC=CC(O)=C11705.8Semi standard non polar33892256
3-Hydroxymandelic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=CC(C(O)C(=O)O)=C11687.9Semi standard non polar33892256
3-Hydroxymandelic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=CC(O)=C11729.4Semi standard non polar33892256
3-Hydroxymandelic acid,2TMS,isomer #2C[Si](C)(C)OC1=CC=CC(C(O[Si](C)(C)C)C(=O)O)=C11747.4Semi standard non polar33892256
3-Hydroxymandelic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C(O)C1=CC=CC(O[Si](C)(C)C)=C11689.4Semi standard non polar33892256
3-Hydroxymandelic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C11753.8Semi standard non polar33892256
3-Hydroxymandelic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C(=O)O)C1=CC=CC(O)=C11985.8Semi standard non polar33892256
3-Hydroxymandelic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=CC(O)=C11945.3Semi standard non polar33892256
3-Hydroxymandelic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC(C(O)C(=O)O)=C11936.0Semi standard non polar33892256
3-Hydroxymandelic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C12174.0Semi standard non polar33892256
3-Hydroxymandelic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(C(O[Si](C)(C)C(C)(C)C)C(=O)O)=C12229.6Semi standard non polar33892256
3-Hydroxymandelic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12176.5Semi standard non polar33892256
3-Hydroxymandelic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12391.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9800000000-bf3bd36839dcaaf08ef92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1091000000-8a56583c49f940049f672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxymandelic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxymandelic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-00di-0900000000-10beec4c3472d3afb28c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxymandelic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-00di-0900000000-5a6c0f2c681a7da489f02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxymandelic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-00dl-9800000000-49e33a7a57260ed160a52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxymandelic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-00di-0900000000-72199f89fe731fcb25d02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxymandelic acid LC-ESI-QTOF , negative-QTOFsplash10-00di-0900000000-72199f89fe731fcb25d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxymandelic acid 20V, Negative-QTOFsplash10-00di-0900000000-09041ce83fd7828817c22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxymandelic acid 10V, Negative-QTOFsplash10-00di-0900000000-c7391a6d5d26c34d6ff12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxymandelic acid 40V, Negative-QTOFsplash10-006x-9800000000-ac2ed19d66c39053866d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 10V, Positive-QTOFsplash10-0v4i-0900000000-33388d527863717e6b522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 20V, Positive-QTOFsplash10-00di-1900000000-d7968efcab4fad804ea02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 40V, Positive-QTOFsplash10-0592-9500000000-c87d3eeded18820fc89e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 10V, Negative-QTOFsplash10-01b9-0900000000-78dab78100ab6d939f862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 20V, Negative-QTOFsplash10-00r7-4900000000-953e2a0259bd8f0d8e1a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 40V, Negative-QTOFsplash10-0006-9100000000-360650692ca61f88e3552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 10V, Positive-QTOFsplash10-0udi-0900000000-d80ec9d424fdb79051802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 20V, Positive-QTOFsplash10-000t-6900000000-e627c37fec0d676dca1a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 40V, Positive-QTOFsplash10-0gb9-9000000000-a4dc421433c86804a2282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 10V, Negative-QTOFsplash10-01b9-0900000000-24344bf18e403a55dd052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 20V, Negative-QTOFsplash10-00dl-7900000000-031a2963cd0c05ff534f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxymandelic acid 40V, Negative-QTOFsplash10-0006-9100000000-87934a19509c4f25a0792021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified10.527 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified10.527 +/- 0.0595 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
UrineDetected and Quantified0.023 +/- 0.014 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified700.0 (670.0 - 1030.0) uMAdult (>18 years old)Both
Kidney disease
    • Nieren- und Hochd...
 details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. (). Nieren- und Hochdruckkrankheiten (1978), 7(2), 62-74 (translated from German Kidney and Hypertension). . .
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022222
KNApSAcK IDNot Available
Chemspider ID78444
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxymandelic acid
METLIN ID732
PubChem Compound86957
PDB IDNot Available
ChEBI ID86553
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFanali S; Aturki Z Further study on the use of uncharged beta-cyclodextrin polymer in capillary electrophoresis: enantiomeric separation of some alpha-hydroxy acids. Electrophoresis (1995), 16(8), 1505-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Midgley JM, Couch MW, Crowley JR, Williams CM: Identification and quantitative determination of o- and m-hydroxymandelic acid in human urine. Biomed Mass Spectrom. 1979 Nov;6(11):485-90. [PubMed:534686 ]
  2. Ibrahim KE, Midgley JM, Crowley JR, Williams CM: The mammalian metabolism of R-(-)-m-synephrine. J Pharm Pharmacol. 1983 Mar;35(3):144-7. [PubMed:6132969 ]
  3. Gumbhir K, Mason WD: Determination of m-hydroxymandelic acid, m-hydroxyphenylglycol and their conjugates in human plasma using liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1994 Jul;12(7):943-9. [PubMed:7981325 ]
  4. 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 ]