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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
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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
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
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
RoleNot 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
Predicted Chromatographic Properties
Spectra
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)Not Available
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 ]
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