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Showing metabocard for Glycolic acid (HMDB0000115)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (9) Show 9 proteinsXML
enzymes (9) Show 9 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:31 UTC
HMDB IDHMDB0000115
Secondary Accession Numbers
  • HMDB0003035
  • HMDB00115
  • HMDB03035
Metabolite Identification
Common NameGlycolic acid
DescriptionGlycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). This colourless, odourless, and hygroscopic crystalline solid is highly soluble in water. Due to its excellent capability to penetrate skin, glycolic acid is often used in skin care products, most often as a chemical peel. It may reduce wrinkles, acne scarring, and hyperpigmentation and improve many other skin conditions, including actinic keratosis, hyperkeratosis, and seborrheic keratosis. Once applied, glycolic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together. This allows the outer skin to dissolve, revealing the underlying skin. It is thought that this is due to the reduction of calcium ion concentrations in the epidermis and the removal of calcium ions from cell adhesions, leading to desquamation. Glycolic acid is a known inhibitor of tyrosinase. This can suppress melanin formation and lead to a lightening of skin colour. Acute doses of glycolic acid on skin or eyes leads to local effects that are typical of a strong acid (e.g. dermal and eye irritation). Glycolate is a nephrotoxin if consumed orally. A nephrotoxin is a compound that causes damage to the kidney and kidney tissues. Glycolic acid's renal toxicity is due to its metabolism to oxalic acid. Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis. Oxalic acid readily precipitates with calcium to form insoluble calcium oxalate crystals. Renal tissue injury is caused by widespread deposition of oxalate crystals and the toxic effects of glycolic acid. Glycolic acid does exhibit some inhalation toxicity and can cause respiratory, thymus, and liver damage if present in very high levels over long periods of time. Elevated glycolic acid without elevated oxalic acid is most likely a result of GI yeast overgrowth (Aspergillus, Penicillium, probably Candida) or due to dietary sources containing glycerol (glycerine). (http://drweyrich.weyrich.com/labs/oat.html). Glycolic acid has also been found to be a metabolite in Acetobacter, Acidithiobacillus, Alcaligenes, Corynebacterium, Cryptococcus, Escherichia, Gluconobacter, Kluyveromyces, Leptospirillum, Pichia, Rhodococcus, Rhodotorula and Saccharomyces (PMID: 11758919 ; PMID: 26360870 ; PMID: 14390024 ).
Structure
Data?1676999671
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000115 (Glycolic acid)


  Mrv1652309032023522D          

  5  4  0  0  0  0            999 V2000
10000.894810001.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.609610000.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.325910001.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.179410000.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.894810001.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
M  END
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3D MOL for HMDB0000115 (Glycolic acid)

HMDB0000115
     RDKit          3D
Glycolic acid
  9  8  0  0  0  0  0  0  0  0999 V2000
    0.5818    1.6591    0.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3893    0.5883    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    0.0447   -0.6953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -0.1396    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.2911   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105    0.2603   -0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    0.5210   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9694   -0.3392    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303   -1.3035   -0.9892 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
  3  6  1  0
  4  7  1  0
  4  8  1  0
  5  9  1  0
M  END
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3D SDF for HMDB0000115 (Glycolic acid)


  Mrv1652309032023522D          

  5  4  0  0  0  0            999 V2000
10000.894810001.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.609610000.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.325910001.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.179410000.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.894810001.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000115

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)

> <INCHI_KEY>
AEMRFAOFKBGASW-UHFFFAOYSA-N

> <FORMULA>
C2H4O3

> <MOLECULAR_WEIGHT>
76.0514

> <EXACT_MASS>
76.016043994

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
6.195837007972227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyacetic acid

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-1.0405937603333335

> <ALOGPS_LOGS>
0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.780077957574235

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.526322592592504

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6133096708862027

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
14.345899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.08e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycolic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000115 (Glycolic acid)

HMDB0000115
     RDKit          3D
Glycolic acid
  9  8  0  0  0  0  0  0  0  0999 V2000
    0.5818    1.6591    0.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3893    0.5883    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    0.0447   -0.6953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -0.1396    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.2911   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105    0.2603   -0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    0.5210   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9694   -0.3392    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303   -1.3035   -0.9892 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
  3  6  1  0
  4  7  1  0
  4  8  1  0
  5  9  1  0
M  END
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PDB for HMDB0000115 (Glycolic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.3378668.618   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.6718667.849   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8671.0088668.618   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8667.0028667.849   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8668.3378670.161   0.000  0.00  0.00           O+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0000115 (Glycolic acid)

COMPND    HMDB0000115
HETATM    1  O1  UNL     1       0.582   1.659   0.783  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.389   0.588   0.167  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.318   0.045  -0.695  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.882  -0.140   0.358  1.00  0.00           C  
HETATM    5  O3  UNL     1      -0.921  -1.291  -0.393  1.00  0.00           O  
HETATM    6  H1  UNL     1       2.311   0.260  -0.683  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.697   0.521  -0.002  1.00  0.00           H  
HETATM    8  H3  UNL     1      -0.969  -0.339   1.455  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.130  -1.304  -0.989  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    6
CONECT    4    5    7    8
CONECT    5    9
END
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SMILES for HMDB0000115 (Glycolic acid)

OCC(O)=O
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INCHI for HMDB0000115 (Glycolic acid)

InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Hydroxyacetic acidChEBI
2-Hydroxyethanoic acidChEBI
alpha-Hydroxyacetic acidChEBI
Glycollic acidChEBI
HOCH2COOHChEBI
Hydroxyacetic acidChEBI
Hydroxyethanoic acidChEBI
2-HydroxyacetateGenerator
2-HydroxyethanoateGenerator
a-HydroxyacetateGenerator
a-Hydroxyacetic acidGenerator
alpha-HydroxyacetateGenerator
Α-hydroxyacetateGenerator
Α-hydroxyacetic acidGenerator
GlycollateGenerator
HydroxyacetateGenerator
HydroxyethanoateGenerator
GlycolateGenerator
GlycocideHMDB
GlyPureHMDB
GlyPure 70HMDB
Sodium glycolateHMDB
Glycolic acid, 2-(14)C-labeledHMDB
Glycolic acid, 1-(14)C-labeledHMDB
Glycolic acid, potassium saltHMDB
Glycolic acid, monopotassium saltHMDB
Glycolic acid, calcium saltHMDB
Glycolic acid, monoammonium saltHMDB
Glycolic acid, monolithium saltHMDB
Glycolic acid, monosodium saltHMDB
Potassium glycolateHMDB
Chemical FormulaC2H4O3
Average Molecular Weight76.0514
Monoisotopic Molecular Weight76.016043994
IUPAC Name2-hydroxyacetic acid
Traditional Nameglycolic acid
CAS Registry Number79-14-1
SMILES
OCC(O)=O
InChI Identifier
InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
InChI KeyAEMRFAOFKBGASW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological roleIndirect biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point75 - 80 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.11HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility608 g/LALOGPS
logP-1ALOGPS
logP-1ChemAxon
logS0.9ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.35 m³·mol⁻¹ChemAxon
Polarizability6.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.58731661259
DarkChem[M-H]-105.17531661259
AllCCS[M+H]+123.25132859911
AllCCS[M-H]-127.33632859911
DeepCCS[M+H]+128.22530932474
DeepCCS[M-H]-125.47630932474
DeepCCS[M-2H]-162.05630932474
DeepCCS[M+Na]+136.46230932474
AllCCS[M+H]+123.332859911
AllCCS[M+H-H2O]+118.832859911
AllCCS[M+NH4]+127.432859911
AllCCS[M+Na]+128.632859911
AllCCS[M-H]-127.332859911
AllCCS[M+Na-2H]-132.932859911
AllCCS[M+HCOO]-139.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glycolic acidOCC(O)=O1922.1Standard polar33892256
Glycolic acidOCC(O)=O800.1Standard non polar33892256
Glycolic acidOCC(O)=O859.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycolic acid,1TMS,isomer #1C[Si](C)(C)OCC(=O)O999.8Semi standard non polar33892256
Glycolic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CO862.9Semi standard non polar33892256
Glycolic acid,2TMS,isomer #1C[Si](C)(C)OCC(=O)O[Si](C)(C)C1084.0Semi standard non polar33892256
Glycolic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)O1249.8Semi standard non polar33892256
Glycolic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CO1098.4Semi standard non polar33892256
Glycolic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)O[Si](C)(C)C(C)(C)C1482.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Glycolic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-ed8b8e4a9e2556ea02e22014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9600000000-8bafc88c7bf4e90fb5e82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid GC-MS (2 TMS)splash10-003r-2910000000-bd50bf5bab6f5327eaf42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid EI-B (Non-derivatized)splash10-001i-9000000000-cadf899be6b15d0083302017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid EI-B (Non-derivatized)splash10-001i-9000000000-e66ed28d8419895e0fb42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid EI-B (Non-derivatized)splash10-0002-0900000000-7f84fac3284d17fa3ba62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-ed8b8e4a9e2556ea02e22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid GC-EI-TOF (Non-derivatized)splash10-00dj-9600000000-8bafc88c7bf4e90fb5e82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid GC-MS (Non-derivatized)splash10-003r-2910000000-bd50bf5bab6f5327eaf42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycolic acid GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-d724c85a3b30e3c2e4bc2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7l-9000000000-1e9466549305eb20257b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (2 TMS) - 70eV, Positivesplash10-05i9-9520000000-5f0019fe63eb6e6921092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycolic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-2885890e3bb8c015742f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-004i-9000000000-e942bdae1d60e5f5d6492012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-00di-9000000000-f225de2de3540c3f50a42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-00di-9000000000-7de217d97b44f53aad822012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-00di-9000000000-88af2b259f82cd1d89382012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-004i-9000000000-c968a24f0640b154325b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0059-9000000000-1dfacf30bf94ce3bf8bb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-88af2b259f82cd1d89382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-c968a24f0640b154325b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ , negative-QTOFsplash10-0059-9000000000-1dfacf30bf94ce3bf8bb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 1V, positive-QTOFsplash10-004i-9000000000-fa715ee3ce9abbc94edb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 2V, positive-QTOFsplash10-004i-9000000000-ace3c5f526d28fd24de92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 3V, positive-QTOFsplash10-004i-9000000000-ff7f922c2460adb6a10d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 4V, positive-QTOFsplash10-004i-9000000000-1d63aaaf9cbc6d3bb3b42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 5V, positive-QTOFsplash10-004j-9000000000-e9c74e7df728e016450c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 6V, positive-QTOFsplash10-002b-9000000000-d0963403f3a8ff9e576d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 7V, positive-QTOFsplash10-002b-9000000000-9e1d6b2e2b889232d6102020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 8V, positive-QTOFsplash10-0002-9000000000-e9824f68b2176db90d332020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 9V, positive-QTOFsplash10-000t-9000000000-02329982bc7150d972bf2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycolic acid QqQ 10V, positive-QTOFsplash10-000t-9000000000-216d8ece56b0a44e52892020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolic acid 10V, Positive-QTOFsplash10-004i-9000000000-d961c3c14ec415e3141e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolic acid 20V, Positive-QTOFsplash10-0a6r-9000000000-67f73be970ba9f885c4a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolic acid 10V, Negative-QTOFsplash10-004i-9000000000-7445713a5fe347bbc8b82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolic acid 20V, Negative-QTOFsplash10-004i-9000000000-26e13242443efc1aa8462015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycolic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-6ba976b949118cd0a86a2015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
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
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart 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
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Bladder
  • Epidermis
  • Fibroblasts
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified50-123 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified34 uMAdult (>18 years old)FemaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.9 +/- 2.4 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.8 +/- 1.7 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified54.0 +/- 50.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal		 details
FecesDetected and Quantified174.882 +/- 63.115 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified8.64 +/- 3.09 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified9.67 +/- 3.35 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified10.7 +/- 1.79 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified10.9 +/- 2.45 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified21.65 +/- 13.0 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected and Quantified20.813-169.475 umol/mmol creatinineChildren (1-13 years old)MaleNormal details
UrineDetected and Quantified68.385-169.475 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified10-24.7 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified10.5-29.0 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified13-27.4 umol/mmol creatinineInfant (0-1 year old)Male
Normal		 details
UrineDetected and Quantified14.2-33.9 umol/mmol creatinineInfant (0-1 year old)Female
Normal		 details
UrineDetected and Quantified67.9 (36.0-324.4) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified23-53 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified<104.0638 umol/mmol creatinineChildren (1 - 13 years old)MaleNormal details
UrineDetected and Quantified<193.261 umol/mmol creatinineInfant (0-1 year old)MaleNormal details
UrineDetected and Quantified30.0 (15.8-52.6) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified41.6 (3.7-122.1) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified38.10 +/- 27.35 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected and Quantified<54.91 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified64.0 (21.0-107.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified32.8 (8.8-71.6) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified248.5(72.0-425.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified169.5 (46.0-293.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified128.0 (48.0-208.0) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified110.0 (34.0-186.0) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified35 (18-55) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified36.667 (13.333-52.667) umol/mmol creatinineChildren (1 - 13 years old)Not SpecifiedNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified26-47 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified39.4 (2.9-78.1) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified190-480 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified74.257 +/- 48.676 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified0-229 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Primary Hyperoxal...
 details
UrineDetected and Quantified39.6 (16.7-89.1) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified77.1 (33.1-122.0) umol/mmol creatinineChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0 uMAdult (>18 years old)FemaleBranched-chain Keto Acid Dehydrogenase Kinase Deficiency details
BloodDetected and Quantified0 uMAdolescent (13-18 years old)FemaleBranched-chain Keto Acid Dehydrogenase Kinase Deficiency details
BloodDetected and Quantified7.3 +/- 10.1 uMAdult (>18 years old)Both
Hemodialysis 		details
BloodDetected and Quantified0.6 +/- 2.3 uMAdult (>18 years old)Both
Hemodialysis		 details
BloodDetected and Quantified48.0 (40.0 - 56.0) uMAdult (>18 years old)BothEthylene Glycol Poisoning details
Cerebrospinal Fluid (CSF)Detected and Quantified1868 uMAdult (>18 years old)BothTransurethral prostatectomy syndrome details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified<20.813 umol/mmol creatinineChildren (1-13 years old)MaleGlutaric acidemia type 2 details
UrineDetected and Quantified52.0319-156.0957 umol/mmol creatinineAdult (>18 years old)FemaleGlutaric acidemia type 2 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified5.947 umol/mmol creatinineInfant (0-1 year old)MaleFumarase deficiency details
UrineDetected and Quantified6.667 umol/mmol creatinineChildren (1 - 13 years old)MaleD-2-Hydroxyglutaric aciduria details
UrineDetected and Quantified163.529 umol/mmol creatinineChildren (1 - 13 years old)MaleD-2-Hydroxyglutaric aciduria details
UrineDetected and Quantified341.924 umol/mmol creatinineChildren (1 - 13 years old)MaleD-2-Hydroxyglutaric aciduria details
UrineDetected and Quantified359.333 umol/mmol creatinineAdult (>18 years old)Male
Primary hyperoxaluria I		 details
UrineDetected and Quantified280.667-1946 umol/mmol creatinineChildren (1-13 years old)BothPrimary hyperoxaluria I details
UrineDetected and Quantified23.0 +/- 14.0 umol/mmol creatinineAdult (>18 years old)BothLung cancer details
UrineDetected and Quantified0.40 +/- 0.36 umol/mmol creatinineAdult (>18 years old)BothBiliary atresia details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia		 details
UrineDetected and Quantified47.009 +/- 25.964 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified>229 umol/mmol creatinineChildren (1-13 years old)BothGlycolic aciduria
    • Primary Hyperoxal...
 details
Associated Disorders and Diseases
Disease References
Ethylene glycol poisoning
  1. Jacobsen D, Hewlett TP, Webb R, Brown ST, Ordinario AT, McMartin KE: Ethylene glycol intoxication: evaluation of kinetics and crystalluria. Am J Med. 1988 Jan;84(1):145-52. [PubMed:3337119 ]
Hemodialysis
  1. Ogawa Y, Machida N, Jahana M, Gakiya M, Chinen Y, Oda M, Morozumi M, Sugaya K: Major factors modulating the serum oxalic acid level in hemodialysis patients. Front Biosci. 2004 Sep 1;9:2901-8. [PubMed:15353324 ]
Branched-chain Keto Acid Dehydrogenase Kinase Deficiency
  1. Novarino G, El-Fishawy P, Kayserili H, Meguid NA, Scott EM, Schroth J, Silhavy JL, Kara M, Khalil RO, Ben-Omran T, Ercan-Sencicek AG, Hashish AF, Sanders SJ, Gupta AR, Hashem HS, Matern D, Gabriel S, Sweetman L, Rahimi Y, Harris RA, State MW, Gleeson JG: Mutations in BCKD-kinase lead to a potentially treatable form of autism with epilepsy. Science. 2012 Oct 19;338(6105):394-7. doi: 10.1126/science.1224631. Epub 2012 Sep 6. [PubMed:22956686 ]
Transurethral resection of the prostate
  1. Perier C, Mahul P, Molliex S, Auboyer C, Frey J: Progressive changes in glycine and glycine derivatives in plasma and cerebrospinal fluid after transurethral prostatic resection. Clin Chem. 1990 Dec;36(12):2152-3. [PubMed:2253377 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  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 ]
  3. 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 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Biliary atresia
  1. Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [PubMed:3944741 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Fumarase deficiency
  1. Bastug O, Kardas F, Ozturk MA, Halis H, Memur S, Korkmaz L, Tag Z, Gunes T: A rare cause of opistotonus; fumaric aciduria: The first case presentation in Turkey. Turk Pediatri Ars. 2014 Mar 1;49(1):74-6. doi: 10.5152/tpa.2014.442. eCollection 2014 Mar. [PubMed:26078636 ]
D-2-hydroxyglutaric aciduria
  1. Chalmers RA, Lawson AM, Watts RW, Tavill AS, Kamerling JP, Hey E, Ogilvie D: D-2-hydroxyglutaric aciduria: case report and biochemical studies. J Inherit Metab Dis. 1980;3(1):11-5. [PubMed:6774165 ]
Primary hyperoxaluria I
  1. Holmgren G, Hornstrom T, Johansson S, Samuelson G: Primary hyperoxaluria (glycolic acid variant): a clinical and genetical investigation of eight cases. Ups J Med Sci. 1978;83(1):65-70. [PubMed:705974 ]
Glycolic aciduria
  1. Coulter-Mackie MB, White CT, Lange D, et al. (2002). Primary Hyperoxaluria Type 1. 2002 Jun 19 [Updated 2014 Jul 17]. In: Adam MP, Ardinger HH, Pagon RA, et al., editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2017. Available from: https://www.ncbi.nlm.nih.gov/books/NBK1283/. University of Washington, Seattle.
Glutaric acidemia type 2
  1. Chlebeck PT, Milliner DS, Smith LH: Long-term prognosis in primary hyperoxaluria type II (L-glyceric aciduria). Am J Kidney Dis. 1994 Feb;23(2):255-9. [PubMed:8311084 ]
Associated OMIM IDs
DrugBank IDDB03085
Phenol Explorer Compound IDNot Available
FooDB IDFDB003298
KNApSAcK IDC00007461
Chemspider ID737
KEGG Compound IDC03547
BioCyc IDGLYCOLLATE
BiGG ID34090
Wikipedia LinkGlycolic_acid
METLIN ID3219
PubChem Compound757
PDB IDNot Available
ChEBI ID17497
Food Biomarker OntologyNot Available
VMH IDGLYCLT
MarkerDB IDMDB00013417
Good Scents IDNot Available
References
Synthesis ReferenceWitzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  2. 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 ]
  3. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  4. Horikoshi T, Matsumoto M, Usuki A, Igarashi S, Hikima R, Uchiwa H, Hayashi S, Brysk MM, Ichihashi M, Funasaka Y: Effects of glycolic acid on desquamation-regulating proteinases in human stratum corneum. Exp Dermatol. 2005 Jan;14(1):34-40. [PubMed:15660917 ]
  5. DiNardo JC, Grove GL, Moy LS: Clinical and histological effects of glycolic acid at different concentrations and pH levels. Dermatol Surg. 1996 May;22(5):421-4. [PubMed:8634803 ]
  6. Marangella M, Petrarulo M, Bianco O, Vitale C, Finocchiaro P, Linari F: Glycolate determination detects type I primary hyperoxaluria in dialysis patients. Kidney Int. 1991 Jan;39(1):149-54. [PubMed:2002628 ]
  7. Tsiafoulis CG, Prodromidis MI, Karayannis MI: Development of amperometric biosensors for the determination of glycolic acid in real samples. Anal Chem. 2002 Jan 1;74(1):132-9. [PubMed:11795781 ]
  8. Porter WH, Rutter PW, Yao HH: Simultaneous determination of ethylene glycol and glycolic acid in serum by gas chromatography-mass spectrometry. J Anal Toxicol. 1999 Nov-Dec;23(7):591-7. [PubMed:10595845 ]
  9. Jacobsen D, Hewlett TP, Webb R, Brown ST, Ordinario AT, McMartin KE: Ethylene glycol intoxication: evaluation of kinetics and crystalluria. Am J Med. 1988 Jan;84(1):145-52. [PubMed:3337119 ]
  10. Bernstein EF, Lee J, Brown DB, Yu R, Van Scott E: Glycolic acid treatment increases type I collagen mRNA and hyaluronic acid content of human skin. Dermatol Surg. 2001 May;27(5):429-33. [PubMed:11359487 ]
  11. Leumann EP, Dietl A, Matasovic A: Urinary oxalate and glycolate excretion in healthy infants and children. Pediatr Nephrol. 1990 Sep;4(5):493-7. [PubMed:2242313 ]
  12. Booth ED, Dofferhoff O, Boogaard PJ, Watson WP: Comparison of the metabolism of ethylene glycol and glycolic acid in vitro by precision-cut tissue slices from female rat, rabbit and human liver. Xenobiotica. 2004 Jan;34(1):31-48. [PubMed:14742135 ]
  13. Mahul P, Molliex S, Auboyer C, Levigne F, Jospe R, Dumont A, Gilloz A: [Neurotoxic role of glycocolle and derivatives in transurethral resection of the prostate]. Ann Fr Anesth Reanim. 1993;12(5):512-4. [PubMed:8311360 ]
  14. Marangella M, Petrarulo M, Vitale C, Cosseddu D, Linari F: Plasma and urine glycolate assays for differentiating the hyperoxaluria syndromes. J Urol. 1992 Sep;148(3 Pt 2):986-9. [PubMed:1507356 ]
  15. Effendy I, Kwangsukstith C, Lee JY, Maibach HI: Functional changes in human stratum corneum induced by topical glycolic acid: comparison with all-trans retinoic acid. Acta Derm Venereol. 1995 Nov;75(6):455-8. [PubMed:8651024 ]
  16. Pien K, van Vlem B, van Coster R, Dacremont G, Piette M: An inherited metabolic disorder presenting as ethylene glycol intoxication in a young adult. Am J Forensic Med Pathol. 2002 Mar;23(1):96-100. [PubMed:11953504 ]
  17. Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20. [PubMed:9267307 ]
  18. Newman N, Newman A, Moy LS, Babapour R, Harris AG, Moy RL: Clinical improvement of photoaged skin with 50% glycolic acid. A double-blind vehicle-controlled study. Dermatol Surg. 1996 May;22(5):455-60. [PubMed:8634809 ]
  19. Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. [PubMed:6592775 ]
  20. Porter WH, Rutter PW, Bush BA, Pappas AA, Dunnington JE: Ethylene glycol toxicity: the role of serum glycolic acid in hemodialysis. J Toxicol Clin Toxicol. 2001;39(6):607-15. [PubMed:11762669 ]
  21. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. [PubMed:26360870 ]
  22. Kataoka M, Sasaki M, Hidalgo AR, Nakano M, Shimizu S: Glycolic acid production using ethylene glycol-oxidizing microorganisms. Biosci Biotechnol Biochem. 2001 Oct;65(10):2265-70. doi: 10.1271/bbb.65.2265. [PubMed:11758919 ]
  23. MARTIN SM, STEEL R: Effect of phosphate on production of organic acids by Aspergillus niger. Can J Microbiol. 1955 Jun;1(6):470-2. [PubMed:14390024 ]

Enzymes

Enzyme Details
1. Glucose-6-phosphate 1-dehydrogenase
General function:
Involved in glucose-6-phosphate dehydrogenase activity
Specific function:
Produces pentose sugars for nucleic acid synthesis and main producer of NADPH reducing power.
Gene Name:
G6PD
Uniprot ID:
P11413
Molecular weight:
62467.88
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Enzyme Details
2. Sulfotransferase family cytosolic 2B member 1
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Glycolic acid → 2-(sulfooxy)acetic aciddetails
Enzyme Details
3. Glyoxylate reductase/hydroxypyruvate reductase
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:
GRHPR
Uniprot ID:
Q9UBQ7
Molecular weight:
35667.875
Reactions
Glycolic acid + NADP → Glyoxylic acid + NADPHdetails
Glycolic acid + NADP → Glyoxylic acid + NADPH + Hydrogen Iondetails
Enzyme Details
4. Cytochrome P450 4A11
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:
CYP4A11
Uniprot ID:
Q02928
Molecular weight:
59347.31
Reactions
Fatty acid + Oxygen + Reduced flavoprotein → Glycolic acid + Oxidized flavoprotein + Waterdetails
Enzyme Details
5. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Glycolic acid → 6-(carboxymethoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Glycolic acid → 3,4,5-trihydroxy-6-[(2-hydroxyacetyl)oxy]oxane-2-carboxylic aciddetails
Enzyme Details
6. Hydroxyacid oxidase 1
General function:
Involved in FMN binding
Specific function:
Has 2-hydroxyacid oxidase activity. Most active on the 2-carbon substrate glycolate, but is also active on 2-hydroxy fatty acids, with high activity towards 2-hydroxy palmitate and 2-hydroxy octanoate.
Gene Name:
HAO1
Uniprot ID:
Q9UJM8
Molecular weight:
40923.945
Reactions
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
Enzyme Details
7. Hydroxyacid oxidase 2
General function:
Involved in FMN binding
Specific function:
Catalyzes the oxidation of L-alpha-hydroxy acids as well as, more slowly, that of L-alpha-amino acids.
Gene Name:
HAO2
Uniprot ID:
Q9NYQ3
Molecular weight:
38838.35
Reactions
Glycolic acid + Oxygen → Glyoxylic acid + Hydrogen peroxidedetails
Enzyme Details
8. Phosphoglycolate phosphatase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGP
Uniprot ID:
A6NDG6
Molecular weight:
34005.69
Reactions
Phosphoglycolic acid + Water → Glycolic acid + Phosphatedetails
Enzyme Details
9. Cytochrome P450 4A22
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate and palmitate. Shows no activity towards arachidonic acid and prostaglandin A1. Lacks functional activity in the kidney and does not contribute to renal 20-hydroxyeicosatetraenoic acid (20-HETE) biosynthesis.
Gene Name:
CYP4A22
Uniprot ID:
Q5TCH4
Molecular weight:
59245.28
Reactions
Fatty acid + Oxygen + Reduced flavoprotein → Glycolic acid + Oxidized flavoprotein + Waterdetails