Cannabis Compound Database: Showing Compound Card for Glyoxylic acid (CDB004804)

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Record Information

Version

1.0

Created at

2020-04-17 18:38:28 UTC

Updated at

2020-12-07 19:10:58 UTC

CannabisDB ID

CDB004804

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Glyoxylic acid

Description

Glyoxylic acid, also known as a-ketoacetate or glyoxalate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Glyoxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom. Glyoxylic acid exists in all living species, ranging from bacteria to humans. L-alanine and glyoxylic acid can be biosynthesized from glycine and pyruvic acid through its interaction with the enzyme serine--pyruvate aminotransferase. In humans, glyoxylic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, Glyoxylic acid has been detected, but not quantified in, tamarinds. This could make glyoxylic acid a potential biomarker for the consumption of these foods. Glyoxylic acid is a potentially toxic compound. Glyoxylic acid, with regard to humans, has been found to be associated with several diseases such as bladder infections and transurethral resection of the prostate; glyoxylic acid has also been linked to the inborn metabolic disorder primary hyperoxaluria I. Glyoxylic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
alpha-Ketoacetic acid	ChEBI
Formylformic acid	ChEBI
Glyoxalate	ChEBI
Glyoxalsaeure	ChEBI
Glyoxylate	ChEBI
Glyoxylsaeure	ChEBI
Oxalaldehydic acid	ChEBI
Oxoethanoic acid	ChEBI
a-Ketoacetate	Generator
a-Ketoacetic acid	Generator
alpha-Ketoacetate	Generator
Α-ketoacetate	Generator
Α-ketoacetic acid	Generator
Formylformate	Generator
Glyoxalic acid	Generator
Oxalaldehydate	Generator
Oxoethanoate	Generator
Oxoacetate	HMDB
Oxoacetic acid	HMDB
Glyoxylic acid, 2-(14)C-labeled	HMDB
Glyoxylic acid, sodium salt	HMDB
Glyoxylic acid, sodium salt, 2-(14)C-labeled	HMDB
Glyoxylic acid, 14c2-labeled	HMDB
Glyoxylic acid, calcium salt	HMDB
Glyoxylic acid, sodium salt, 14C-labeled	HMDB

Chemical Formula

C₂H₂O₃

Average Molecular Weight

74.04

Monoisotopic Molecular Weight

74.0004

IUPAC Name

2-oxoacetic acid

Traditional Name

glyoxylic acid

CAS Registry Number

298-12-4

SMILES

OC(=O)C=O

InChI Identifier

InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)

InChI Key

HHLFWLYXYJOTON-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:16891 )
aldehydic acid (CHEBI:16891 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

All tissues

Biofluid and excreta:

Subcellular:

Role

Indirect biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-93 °C	Not Available
Boiling Point	111 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.59	ALOGPS
logP	-0.13	ChemAxon
logS	0.48	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	-9.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	13.5 m³·mol⁻¹	ChemAxon
Polarizability	5.35 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004l-9000000000-a04bafbf8e0b990094a3	2014-09-20	View Spectrum
GC-MS	Glyoxylic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-03di-3900000000-16bc69e0e9d51e54854e	Spectrum
GC-MS	Glyoxylic acid, non-derivatized, GC-MS Spectrum	splash10-03di-3900000000-16bc69e0e9d51e54854e	Spectrum
Predicted GC-MS	Glyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0096-9000000000-042540a05be250278f8b	Spectrum
Predicted GC-MS	Glyoxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-9200000000-c60b627ed670285ec37f	Spectrum
Predicted GC-MS	Glyoxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glyoxylic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9000000000-72c34bc34b8c3341442b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9000000000-920a0dc738957201d4ba	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00di-9000000000-857c7f2d72c3d4c10dbf	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-9b5825d5d9d8b094fefa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-de556f03ea428deff5e2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00dl-9000000000-74b253632894213d473c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-9b5825d5d9d8b094fefa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-de556f03ea428deff5e2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00dl-9000000000-74b253632894213d473c	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-a8cc2c89793394fdf9e4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-d20183b08984d4766e8a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-ea9968e3933fd734506c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-cef8efc477a2500a7ead	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-3817c0865df629803538	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-bb935f857fb5fd08c7e3	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-8f50f0d32d4c40b5b935	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-b6216caa16afdf328489	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-aa6a654e73df38a43273	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-c6f38ec60bcf8724ecd1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-c6f38ec60bcf8724ecd1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-641421c616a0929ce01e	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Alanine Metabolism
Glycine and Serine Metabolism
Primary Hyperoxaluria Type I		Not Available
Pyruvate Carboxylase Deficiency		Not Available
Lactic Acidemia		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
D-amino-acid oxidase	DAO	12q24	P14920	details
Peptidyl-glycine alpha-amidating monooxygenase	PAM	5q14-q21	P19021	details
Glyoxylate reductase/hydroxypyruvate reductase	GRHPR	9q12	Q9UBQ7	details
Alanine--glyoxylate aminotransferase 2, mitochondrial	AGXT2	5p13	Q9BYV1	details
Hydroxyacid oxidase 1	HAO1	20p12	Q9UJM8	details
Hydroxyacid oxidase 2	HAO2	1p13.3-p13.1	Q9NYQ3	details
Serine--pyruvate aminotransferase	AGXT	2q37.3	P21549	details
Kynurenine--oxoglutarate transaminase 3	CCBL2	1p22.2	Q6YP21	details
Probable 4-hydroxy-2-oxoglutarate aldolase, mitochondrial	HOGA1	10q24.2	Q86XE5	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Monocarboxylate transporter 4	SLC16A3	17q25	O15427	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Peptidyl-glycine alpha-amidating monooxygenase	PAM	5q14-q21	P19021	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000119

DrugBank ID

DB04343

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16891

References

General References

Not Available

Only showing the first 10 proteins. There are 11 proteins in total.

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Enzymes

Enzyme Details

1. D-amino-acid oxidase

General function:: Involved in D-amino-acid oxidase activity
Specific function:: Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:: DAO
Uniprot ID:: P14920
Molecular weight:: 39473.75

Enzyme Details

2. Peptidyl-glycine alpha-amidating monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Bifunctional enzyme that catalyzes 2 sequential steps in C-terminal alpha-amidation of peptides. The monooxygenase part produces an unstable peptidyl(2-hydroxyglycine) intermediate that is dismutated to glyoxylate and the corresponding desglycine peptide amide by the lyase part. C-terminal amidation of peptides such as neuropeptides is essential for full biological activity.
Gene Name:: PAM
Uniprot ID:: P19021
Molecular weight:: 108402.425

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

Enzyme Details

4. Alanine--glyoxylate aminotransferase 2, mitochondrial

General function:: Involved in transaminase activity
Specific function:: Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:: AGXT2
Uniprot ID:: Q9BYV1
Molecular weight:: 57155.905

Enzyme Details

5. 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

Enzyme Details

6. 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

Enzyme Details

7. Serine--pyruvate aminotransferase

General function:: Involved in metabolic process
Specific function:: Not Available
Gene Name:: AGXT
Uniprot ID:: P21549
Molecular weight:: 43009.535

Enzyme Details

8. Kynurenine--oxoglutarate transaminase 3

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:: CCBL2
Uniprot ID:: Q6YP21
Molecular weight:: 51399.855

Enzyme Details

9. Probable 4-hydroxy-2-oxoglutarate aldolase, mitochondrial

General function:: Not Available
Specific function:: Catalyzes the final step in the metabolic pathway of hydroxyproline (Probable).
Gene Name:: HOGA1
Uniprot ID:: Q86XE5
Molecular weight:: 17953.475

Transporters

Enzyme Details

1. Monocarboxylate transporter 4

General function:: Involved in transmembrane transport
Specific function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:: SLC16A3
Uniprot ID:: O15427
Molecular weight:: 49468.9

Only showing the first 10 proteins. There are 11 proteins in total.

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Showing Compound Card for Glyoxylic acid (CDB004804)

Structure for CDB004804 (Glyoxylic acid)

Enzymes

Transporters