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Showing metabocard for Mandelic acid (HMDB0000703)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2025-04-10 18:18:00 UTC
HMDB IDHMDB0000703
Secondary Accession Numbers
  • HMDB00703
Metabolite Identification
Common NameMandelic acid
DescriptionIt is an isomer of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and oxymethylbenzoic acid (2-methoxybenzoic acid). Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-o-methyl transferase. It is also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes. Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C8H8O3. It is a white crystalline solid that is soluble in water and most common organic solvents. Mandelic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism. Mandelic acid is elevated by a factor of four or more in the urine of patients with diet-controlled PKU or phenylketonuria (PMID: 37446577 ).
Structure
Data?1676999705
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000703 (Mandelic acid)

  Mrv1652305271900202D          

 11 11  0  0  1  0            999 V2000
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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    0.0000    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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
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3D MOL for HMDB0000703 (Mandelic acid)

HMDB0000703
     RDKit          3D
Mandelic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.7443    1.5659    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770    0.5290    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165   -0.2578    1.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    0.0975   -0.4273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9162   -1.0882   -0.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821    0.0091   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085    1.0441   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859    0.9897   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -0.1082    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703   -1.1598    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -1.0805    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0757   -0.1424    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5813    0.8752   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934   -0.8971   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445    1.9241   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838    1.8351   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9479   -0.1821    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -2.0449    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.9087    0.6596 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  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  6
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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3D SDF for HMDB0000703 (Mandelic acid)

  Mrv1652305271900202D          

 11 11  0  0  1  0            999 V2000
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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    0.0000    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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000703

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H](C(O)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1

> <INCHI_KEY>
IWYDHOAUDWTVEP-ZETCQYMHSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.656944642404099

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-hydroxy-2-phenylacetic acid

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.8958356446666668

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.568490699995834

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.751233575646761

> <JCHEM_PKA_STRONGEST_BASIC>
-4.110158859648652

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
38.7038

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-mandelic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000703 (Mandelic acid)

HMDB0000703
     RDKit          3D
Mandelic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.7443    1.5659    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770    0.5290    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165   -0.2578    1.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    0.0975   -0.4273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9162   -1.0882   -0.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821    0.0091   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085    1.0441   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859    0.9897   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -0.1082    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703   -1.1598    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -1.0805    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0757   -0.1424    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5813    0.8752   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934   -0.8971   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445    1.9241   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838    1.8351   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9479   -0.1821    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -2.0449    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.9087    0.6596 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  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  6
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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PDB for HMDB0000703 (Mandelic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0000703 (Mandelic acid)

COMPND    HMDB0000703
HETATM    1  O1  UNL     1       1.744   1.566   1.395  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.077   0.529   0.800  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.116  -0.258   1.276  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.384   0.097  -0.427  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.916  -1.088  -0.929  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.082   0.009  -0.250  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.909   1.044  -0.666  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.286   0.990  -0.514  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.878  -0.108   0.062  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.070  -1.160   0.488  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.701  -1.081   0.324  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.076  -0.142   0.915  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.581   0.875  -1.204  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.893  -0.897  -1.087  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.445   1.924  -1.127  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.884   1.835  -0.861  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.948  -0.182   0.196  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.520  -2.045   0.950  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.065  -1.909   0.660  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    6   13
CONECT    5   14
CONECT    6    7    7   11
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   10   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for HMDB0000703 (Mandelic acid)

O[C@H](C(O)=O)C1=CC=CC=C1
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INCHI for HMDB0000703 (Mandelic acid)

InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name(2S)-2-hydroxy-2-phenylacetic acid
Traditional Name(S)-mandelic acid
CAS Registry Number90-64-2
SMILES
O[C@H](C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
InChI KeyIWYDHOAUDWTVEP-ZETCQYMHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point120 - 122 °CNot Available
Boiling Point321.83 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility181 mg/mLNot Available
LogP0.62HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available131.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00002103
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
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 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Phenylketonuria
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
  2. Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB03357
Phenol Explorer Compound IDNot Available
FooDB IDFDB022191
KNApSAcK IDC00037426
Chemspider ID388690
KEGG Compound IDC01984
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMandelic acid
METLIN ID5671
PubChem Compound439616
PDB IDNot Available
ChEBI ID32800
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000228
Good Scents IDrw1136021
References
Synthesis ReferenceChen, Jianfeng; Chen, Hao. Process for preparation of mandelic acid by membrane separation technology. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 7pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References