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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9) Show 9 proteins XML

enzymes (9) Show 9 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-11-09 23:12:05 UTC

HMDB ID

HMDB0000115

Secondary Accession Numbers

HMDB0003035
HMDB00115
HMDB03035

Metabolite Identification

Common Name

Glycolic acid

Description

Glycolic 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxyacetic acid	ChEBI
2-Hydroxyethanoic acid	ChEBI
alpha-Hydroxyacetic acid	ChEBI
Glycollic acid	ChEBI
HOCH2COOH	ChEBI
Hydroxyacetic acid	ChEBI
Hydroxyethanoic acid	ChEBI
2-Hydroxyacetate	Generator
2-Hydroxyethanoate	Generator
a-Hydroxyacetate	Generator
a-Hydroxyacetic acid	Generator
alpha-Hydroxyacetate	Generator
Α-hydroxyacetate	Generator
Α-hydroxyacetic acid	Generator
Glycollate	Generator
Hydroxyacetate	Generator
Hydroxyethanoate	Generator
Glycolate	Generator
Glycocide	HMDB
GlyPure	HMDB
GlyPure 70	HMDB
Sodium glycolate	HMDB
Glycolic acid, 2-(14)C-labeled	HMDB
Glycolic acid, 1-(14)C-labeled	HMDB
Glycolic acid, potassium salt	HMDB
Glycolic acid, monopotassium salt	HMDB
Glycolic acid, calcium salt	HMDB
Glycolic acid, monoammonium salt	HMDB
Glycolic acid, monolithium salt	HMDB
Glycolic acid, monosodium salt	HMDB
Potassium glycolate	HMDB

Chemical Formula

C₂H₄O₃

Average Molecular Weight

76.0514

Monoisotopic Molecular Weight

76.016043994

IUPAC Name

2-hydroxyacetic acid

Traditional Name

glycolic acid

CAS Registry Number

79-14-1

SMILES

OCC(O)=O

InChI Identifier

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

InChI Key

AEMRFAOFKBGASW-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:17497 )
2-hydroxy monocarboxylic acid (CHEBI:17497 )

Ontology

Physiological effect

Adverse health effect

Respiratory system disorder

Pulmonary disorder

Lung cancer

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis

Hepatobiliary disorder

Biliary disorder

Biliary atresia - Reduced in human urine (PMID: 3944741 ).

Genetic disorder

Inborn errors of metabolism

Organic acidemia

Fumarase deficiency - Reduced in human urine (PMID: 26078636 ).
D-2-hydroxyglutaric aciduria - Elevated in human urine (PMID: 6774165 ).
Primary hyperoxaluria i - Elevated in human urine (PMID: 705974 ).

Epidermis

Excreta

Cellular substructure

Macromolecular complex

Organelle

Peroxisome

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	75 - 80 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.11	HANSCH,C ET AL. (1995)

Experimental Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	608 g/L	ALOGPS
logP	10^(-1) g/L	ALOGPS
logP	10^(-1) g/L	ChemAxon
logS	10^(0.9) g/L	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	14.35 m³·mol⁻¹	ChemAxon
Polarizability	6.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	112.587	31661259
DarkChem	[M-H]-	105.175	31661259
AllCCS	[M+H]+	123.251	32859911
AllCCS	[M-H]-	127.336	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycolic acid,1TMS,#1	C[Si](C)(C)OCC(=O)O	999.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
Glycolic acid,1TMS,#2	C[Si](C)(C)OC(=O)CO	862.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
Glycolic acid,2TMS,#1	C[Si](C)(C)OCC(=O)O[Si](C)(C)C	1084.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
Glycolic acid,1TBDMS,#1	CC(C)(C)[Si](C)(C)OCC(=O)O	1249.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
Glycolic acid,1TBDMS,#2	CC(C)(C)[Si](C)(C)OC(=O)CO	1098.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
Glycolic acid,2TBDMS,#1	CC(C)(C)[Si](C)(C)OCC(=O)O[Si](C)(C)C(C)(C)C	1482.3	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Glycolic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid GC-MS (2 TMS)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid EI-B (Non-derivatized)	splash10-001i-9000000000-cadf899be6b15d008330	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid EI-B (Non-derivatized)	splash10-001i-9000000000-e66ed28d8419895e0fb4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid EI-B (Non-derivatized)	splash10-0002-0900000000-7f84fac3284d17fa3ba6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid GC-EI-TOF (Non-derivatized)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid GC-MS (Non-derivatized)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycolic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-d724c85a3b30e3c2e4bc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7l-9000000000-1e9466549305eb20257b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycolic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05i9-9520000000-5f0019fe63eb6e692109	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycolic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycolic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-2885890e3bb8c015742f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-004i-9000000000-e942bdae1d60e5f5d649	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-00di-9000000000-f225de2de3540c3f50a4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-00di-9000000000-7de217d97b44f53aad82	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-00di-9000000000-88af2b259f82cd1d8938	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-004i-9000000000-c968a24f0640b154325b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ , negative-QTOF	splash10-00di-9000000000-88af2b259f82cd1d8938	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-c968a24f0640b154325b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid LC-ESI-QQ , negative-QTOF	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 1V, positive-QTOF	splash10-004i-9000000000-fa715ee3ce9abbc94edb	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 2V, positive-QTOF	splash10-004i-9000000000-ace3c5f526d28fd24de9	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 3V, positive-QTOF	splash10-004i-9000000000-ff7f922c2460adb6a10d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 4V, positive-QTOF	splash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 5V, positive-QTOF	splash10-004j-9000000000-e9c74e7df728e016450c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 6V, positive-QTOF	splash10-002b-9000000000-d0963403f3a8ff9e576d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 7V, positive-QTOF	splash10-002b-9000000000-9e1d6b2e2b889232d610	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 8V, positive-QTOF	splash10-0002-9000000000-e9824f68b2176db90d33	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 9V, positive-QTOF	splash10-000t-9000000000-02329982bc7150d972bf	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycolic acid QqQ 10V, positive-QTOF	splash10-000t-9000000000-216d8ece56b0a44e5289	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycolic acid 10V, Positive-QTOF	splash10-004i-9000000000-d961c3c14ec415e3141e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycolic acid 20V, Positive-QTOF	splash10-0a6r-9000000000-67f73be970ba9f885c4a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycolic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycolic acid 10V, Negative-QTOF	splash10-004i-9000000000-7445713a5fe347bbc8b8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycolic acid 20V, Negative-QTOF	splash10-004i-9000000000-26e13242443efc1aa846	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycolic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-6ba976b949118cd0a86a	2015-04-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Mitochondria
Peroxisome

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Bladder
Epidermis
Fibroblasts
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	50-123 uM	Adolescent (13-18 years old)	Female	Normal	22956686	details
Blood	Detected and Quantified	34 uM	Adult (>18 years old)	Female	Normal	22956686	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	7.9 +/- 2.4 uM	Adult (>18 years old)	Both	Normal	1507356	details
Blood	Detected and Quantified	7.8 +/- 1.7 uM	Adult (>18 years old)	Both	Normal	2002628	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	54.0 +/- 50.0 uM	Adult (>18 years old)	Not Specified	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected and Quantified	174.882 +/- 63.115 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25670064	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	8.64 +/- 3.09 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	9.67 +/- 3.35 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	12097436	details
Saliva	Detected and Quantified	10.7 +/- 1.79 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	10.9 +/- 2.45 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	21.65 +/- 13.0 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	20.813-169.475 umol/mmol creatinine	Children (1-13 years old)	Male	Normal	8311084	details
Urine	Detected and Quantified	68.385-169.475 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	8311084	details
Urine	Detected and Quantified	10-24.7 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	10.5-29.0 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	13-27.4 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	14.2-33.9 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	67.9 (36.0-324.4) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	23-53 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	<104.0638 umol/mmol creatinine	Children (1 - 13 years old)	Male	Normal	6774165	details
Urine	Detected and Quantified	<193.261 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	26078636	details
Urine	Detected and Quantified	30.0 (15.8-52.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	41.6 (3.7-122.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	38.10 +/- 27.35 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	2026685	details
Urine	Detected and Quantified	<54.91 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	64.0 (21.0-107.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9267307	details
Urine	Detected and Quantified	32.8 (8.8-71.6) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	248.5(72.0-425.0) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2242313	details
Urine	Detected and Quantified	169.5 (46.0-293.0) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2242313	details
Urine	Detected and Quantified	128.0 (48.0-208.0) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	2242313	details
Urine	Detected and Quantified	110.0 (34.0-186.0) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	2242313	details
Urine	Detected and Quantified	35 (18-55) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	36.667 (13.333-52.667) umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	26-47 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	39.4 (2.9-78.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	190-480 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details
Urine	Detected and Quantified	74.257 +/- 48.676 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	0-229 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Primary Hyperoxal...	details
Urine	Detected and Quantified	39.6 (16.7-89.1) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	77.1 (33.1-122.0) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0 uM	Adult (>18 years old)	Female	Branched-chain Keto Acid Dehydrogenase Kinase Deficiency	22956686	details
Blood	Detected and Quantified	0 uM	Adolescent (13-18 years old)	Female	Branched-chain Keto Acid Dehydrogenase Kinase Deficiency	22956686	details
Blood	Detected and Quantified	7.3 +/- 10.1 uM	Adult (>18 years old)	Both	Hemodialysis	15353324	details
Blood	Detected and Quantified	0.6 +/- 2.3 uM	Adult (>18 years old)	Both	Hemodialysis	15353324	details
Blood	Detected and Quantified	48.0 (40.0 - 56.0) uM	Adult (>18 years old)	Both	Ethylene Glycol Poisoning	3337119	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1868 uM	Adult (>18 years old)	Both	Transurethral prostatectomy syndrome	2253377	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	<20.813 umol/mmol creatinine	Children (1-13 years old)	Male	Glutaric acidemia type 2	8311084	details
Urine	Detected and Quantified	52.0319-156.0957 umol/mmol creatinine	Adult (>18 years old)	Female	Glutaric acidemia type 2	8311084	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	5.947 umol/mmol creatinine	Infant (0-1 year old)	Male	Fumarase deficiency	26078636	details
Urine	Detected and Quantified	6.667 umol/mmol creatinine	Children (1 - 13 years old)	Male	D-2-Hydroxyglutaric aciduria	6774165	details
Urine	Detected and Quantified	163.529 umol/mmol creatinine	Children (1 - 13 years old)	Male	D-2-Hydroxyglutaric aciduria	6774165	details
Urine	Detected and Quantified	341.924 umol/mmol creatinine	Children (1 - 13 years old)	Male	D-2-Hydroxyglutaric aciduria	6774165	details
Urine	Detected and Quantified	359.333 umol/mmol creatinine	Adult (>18 years old)	Male	Primary hyperoxaluria I	705974	details
Urine	Detected and Quantified	280.667-1946 umol/mmol creatinine	Children (1-13 years old)	Both	Primary hyperoxaluria I	705974	details
Urine	Detected and Quantified	23.0 +/- 14.0 umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	18953024	details
Urine	Detected and Quantified	0.40 +/- 0.36 umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	3944741	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details
Urine	Detected and Quantified	47.009 +/- 25.964 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	>229 umol/mmol creatinine	Children (1-13 years old)	Both	Glycolic aciduria	Primary Hyperoxal...	details

Associated Disorders and Diseases

Disease References

Ethylene glycol poisoning
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
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
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
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
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 ] 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 ] 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
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
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
(). Mordechai, Hien, and David S. Wishart. .
Schizophrenia
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
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
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
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
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
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

614923 (Branched-chain Keto Acid Dehydrogenase Kinase Deficiency)
114500 (Colorectal cancer)
211980 (Lung Cancer)
210500 (Biliary atresia)
610247 (Eosinophilic esophagitis)
181500 (Schizophrenia)
606812 (Fumarase deficiency)
600721 (D-2-hydroxyglutaric aciduria)
259900 (Glycolic aciduria)
231680 (Glutaric acidemia type 2)

External Links

DrugBank ID

DB03085

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17497

Food Biomarker Ontology

Not Available

VMH ID

GLYCLT

MarkerDB ID

MDB00013417

Good Scents ID

Not Available

References

Synthesis Reference

Witzemann, 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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. [PubMed:6592775 ]
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 ]
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 ]
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 ]
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

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 ]
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 acid	details

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 + NADPH	details
Glycolic acid + NADP → Glyoxylic acid + NADPH + Hydrogen Ion	details

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 + Water	details

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 acid	details
Glycolic acid → 3,4,5-trihydroxy-6-[(2-hydroxyacetyl)oxy]oxane-2-carboxylic acid	details

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 peroxide	details

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 peroxide	details

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 + Phosphate	details

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 + Water	details

Showing metabocard for Glycolic acid (HMDB0000115)

MOL for HMDB0000115 (Glycolic acid)

3D MOL for HMDB0000115 (Glycolic acid)

3D SDF for HMDB0000115 (Glycolic acid)

3D-SDF for HMDB0000115 (Glycolic acid)

PDB for HMDB0000115 (Glycolic acid)

3D PDB for HMDB0000115 (Glycolic acid)

SMILES for HMDB0000115 (Glycolic acid)

INCHI for HMDB0000115 (Glycolic acid)

Structure for HMDB0000115 (Glycolic acid)

3D Structure for HMDB0000115 (Glycolic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Reactions

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