ECMDB: Glycolate (ECMDB23741) (M2MDB004153)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (6)XML

Proteins (1887)

Record Information

Version

2.0

Creation Date

2015-06-04 15:12:30 -0600

Update Date

2015-08-05 16:22:04 -0600

Secondary Accession Numbers

ECMDB23741

Identification

Name:

Glycolate

Description

A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Hydroxyacetate
2-Hydroxyacetic acid
a-Hydroxyacetate
a-Hydroxyacetic acid
alpha-Hydroxyacetate
alpha-Hydroxyacetic acid
Glycocide
Glycolate
Glycolic acid
Glycollate
Glycollic acid
GlyPure
GlyPure 70
Hydroxyacetate
Hydroxyacetic acid
Hydroxyethanoate
Hydroxyethanoic acid
Sodium glycolate
Sodium glycolic acid
α-Hydroxyacetate
α-Hydroxyacetic acid

Chemical Formula:

C₂H₄O₃

Weight:

Average: 76.0514
Monoisotopic: 76.016043994

InChI Key:

AEMRFAOFKBGASW-UHFFFAOYSA-N

InChI:

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

CAS number:

79-14-1

IUPAC Name:

2-hydroxyacetic acid

Traditional IUPAC Name:

glycolic acid

SMILES:

OCC(O)=O

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 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	608 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1	ChemAxon
logS	0.9	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP
Phosphoglycolic acid + Water <> Glycolic acid + Phosphate + Glycolate
Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP
Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP

SMPDB Pathways:

Not Available

KEGG Pathways:

Glycine, serine and threonine metabolism ec00260
Glyoxylate and dicarboxylate metabolism ec00630
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Pentose phosphate pathway ec00030
Pyruvate metabolism ec00620

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-cadf899be6b15d008330	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-e66ed28d8419895e0fb4	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0900000000-7f84fac3284d17fa3ba6	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-ed8b8e4a9e2556ea02e2	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003r-2910000000-bd50bf5bab6f5327eaf4	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-d724c85a3b30e3c2e4bc	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7l-9000000000-1e9466549305eb20257b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05i9-9520000000-5f0019fe63eb6e692109	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-9000000000-e942bdae1d60e5f5d649	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-f225de2de3540c3f50a4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-7de217d97b44f53aad82	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-88af2b259f82cd1d8938	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-c968a24f0640b154325b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-88af2b259f82cd1d8938	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-c968a24f0640b154325b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-9000000000-1dfacf30bf94ce3bf8bb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-004i-9000000000-fa715ee3ce9abbc94edb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 2V, positive	splash10-004i-9000000000-ace3c5f526d28fd24de9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-004i-9000000000-ff7f922c2460adb6a10d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-004j-9000000000-e9c74e7df728e016450c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-002b-9000000000-d0963403f3a8ff9e576d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-002b-9000000000-9e1d6b2e2b889232d610	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0002-9000000000-e9824f68b2176db90d33	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-000t-9000000000-02329982bc7150d972bf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-000t-9000000000-216d8ece56b0a44e5289	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-d961c3c14ec415e3141e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-67f73be970ba9f885c4a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-7445713a5fe347bbc8b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-26e13242443efc1aa846	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6ba976b949118cd0a86a	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-2885890e3bb8c015742f	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17497
HMDB ID	HMDB0000115
Pubchem Compound ID	757
Kegg ID	C00160
ChemSpider ID	737
Wikipedia ID	Glycolic_acid
BioCyc ID	Not Available

Enzymes

Protein Details

1. Glycolate oxidase subunit glcD

General function:: Involved in catalytic activity
Specific function:: Specific function unknown
Gene Name:: glcD
Uniprot ID:: P0AEP9
Molecular weight:: 53811

Protein Details

2. Lactaldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Acts on lactaldehyde as well as other aldehydes
Gene Name:: aldA
Uniprot ID:: P25553
Molecular weight:: 52272

Reactions

(S)-lactaldehyde + NAD(+) + H(2)O = (S)-lactate + NADH.
Glycolaldehyde + NAD(+) + H(2)O = glycolate + NADH.

Protein Details

3. Phosphoglycolate phosphatase

General function:: Involved in catalytic activity
Specific function:: Specifically catalyzes the dephosphorylation of 2- phosphoglycolate. Is involved in the dissimilation of the intracellular 2-phosphoglycolate formed during the DNA repair of 3'-phosphoglycolate ends, a major class of DNA lesions induced by oxidative stress
Gene Name:: gph
Uniprot ID:: P32662
Molecular weight:: 27389

Reactions

2-phosphoglycolate + H(2)O = glycolate + phosphate.

Protein Details

4. Glycolate oxidase iron-sulfur subunit

General function:: Involved in iron-sulfur cluster binding
Specific function:: Specific function unknown
Gene Name:: glcF
Uniprot ID:: P52074
Molecular weight:: 45110

Protein Details

5. Glyoxylate/hydroxypyruvate reductase A

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Inactive towards 2-oxo-D-gluconate, 2-oxoglutarate, oxaloacetate and pyruvate. Only D- and L-glycerate are involved in the oxidative activity with NADP. Activity with NAD is very low
Gene Name:: ghrA
Uniprot ID:: P75913
Molecular weight:: 35343

Reactions

Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.

Protein Details

6. Glycolate oxidase subunit glcE

General function:: Involved in catalytic activity
Specific function:: Specific function unknown
Gene Name:: glcE
Uniprot ID:: P52073
Molecular weight:: 38361

Glycolate (ECMDB23741) (M2MDB004153)

Structure for #<Compound:0xa65ebea0>

Enzymes

Reactions

Reactions

Reactions