Bovine Metabolome Database: Showing metabocard for Guanidoacetic acid (BMDB0000128)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:56 UTC

Update Date

2020-05-19 22:01:34 UTC

BMDB ID

BMDB0000128

Secondary Accession Numbers

BMDB00128

Metabolite Identification

Common Name

Guanidoacetic acid

Description

Guanidoacetic acid, also known as guanidoacetic acid or Guanidoacetic acid, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Guanidoacetic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). Guanidoacetic acid exists in all living organisms, ranging from bacteria to humans. Guanidoacetic acid participates in a number of enzymatic reactions, within cattle. In particular, Guanidoacetic acid and orotidylic acid can be biosynthesized from glycine and L-arginine through the action of the enzyme glycine amidinotransferase, mitochondrial. In addition, Guanidoacetic acid and S-adenosylhomocysteine can be converted into S-adenosylmethionine and creatine; which is mediated by the enzyme guanidoacetic acid N-methyltransferase. In cattle, guanidoacetic acid is involved in the metabolic pathway called the glycine and serine metabolism pathway. Guanidoacetic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Glycocyamine	ChEBI
Guanidinoacetate	ChEBI
N-(Carbamimidoyl)glycine	ChEBI
N-[Amino(imino)methyl]glycine	ChEBI
N-Amidinoglycine	ChEBI
Guanidinoacetic acid	Kegg
Guanidoacetate	Generator
(Carboxymethyl)-guanidine	HMDB
2-[[Amino(imino)methyl]amino]acetate	HMDB
2-[[Amino(imino)methyl]amino]acetic acid	HMDB
a-Guanidinoacetate	HMDB
a-Guanidinoacetic acid	HMDB
alpha-Guanidinoacetate	HMDB
alpha-Guanidinoacetic acid	HMDB
b-Guanidinoacetate	HMDB
b-Guanidinoacetic acid	HMDB
beta-Guanidinoacetate	HMDB
beta-Guanidinoacetic acid	HMDB
Betacyamine	HMDB
Betasyamine	HMDB
Guanidineacetate	HMDB
Guanidineacetic acid	HMDB
Guanidylacetate	HMDB
Guanidylacetic acid	HMDB
Guanyl glycine	HMDB
N-Amidino-glycine	HMDB
[(Aminoiminomethyl)amino]-acetate	HMDB
[(Aminoiminomethyl)amino]-acetic acid	HMDB
Glycocyamine, 2-(14)C-labeled	HMDB
Glycocyamine, ion (1-)	HMDB
Glycocyamine monohydrochloride	HMDB

Chemical Formula

C₃H₇N₃O₂

Average Molecular Weight

117.1066

Monoisotopic Molecular Weight

117.053826483

IUPAC Name

2-carbamimidamidoacetic acid

Traditional Name

glycocyamine

CAS Registry Number

352-97-6

SMILES

NC(=N)NCC(O)=O

InChI Identifier

InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)

InChI Key

BPMFZUMJYQTVII-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Guanidine
Carboximidamide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glycine derivative (CHEBI:16344 )
N-amidino-amino acid (CHEBI:16344 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.6 mg/mL at 15 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-3.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	12.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.72 m³·mol⁻¹	ChemAxon
Polarizability	10.54 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

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0901000000-4a89fe463d29379e6339	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0911000000-542baca9dcca73225bf0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-0911200000-bb7ea068f193f39c283b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0901000000-4a89fe463d29379e6339	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0911000000-542baca9dcca73225bf0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-0911200000-bb7ea068f193f39c283b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-c703c631a81e400681bd	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9700000000-1dae820000c4f9ec1662	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-016r-7900000000-4777d20e1ab29262427e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dl-9000000000-a1b5501bf0f7a9b0489d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-b61a48cf749b57a2c77e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0gk9-7900000000-5ba298286886c1fabdf5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00di-9100000000-a5b77a913821d637210f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-9100000000-a5b77a913821d637210f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gk9-7900000000-5ba298286886c1fabdf5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-6900000000-4d655a894c702bdfdb59	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-1b831140a3071dd98e0c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9300000000-b27aea734be08f5d2ddc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9000000000-dea2f28faa5430d7e56f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-9500000000-1ba345c7064e9cb70f9c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-6864d4355d3462fbc69f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-1c36299ab8746bbf67a5	View in MoNA
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

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Brain
Kidney
Liver
Mammary Gland
Placenta
Ruminal Fluid

Pathways

Name	SMPDB/Pathwhiz	KEGG
Arginine and Proline Metabolism		Not Available
Glycine and Serine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25599412	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25599412	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000128

DrugBank ID

DB02751

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005417

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16344

References

Synthesis Reference

Thalhammer, Franz; Gastner, Thomas. Preparation of creatine, creatine monohydrate and guanidinoacetic acid. Ger. Offen. (2007), 5pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Guanidinoacetate N-methyltransferase

General function:: Involved in guanidinoacetate N-methyltransferase activity
Specific function:: Converts guanidinoacetate to creatine, using S-adenosylmethionine as the methyl donor. Important in nervous system development.
Gene Name:: GAMT
Uniprot ID:: Q2TBQ3
Molecular weight:: 26610.0

Reactions

S-Adenosylmethionine + Guanidoacetic acid → S-Adenosylhomocysteine + Creatine	details
Guanidoacetic acid + S-Adenosylhomocysteine → S-Adenosylmethionine + Creatine	details

Enzyme Details

2. Glycine amidinotransferase, mitochondrial

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development (By similarity).
Gene Name:: GATM
Uniprot ID:: Q2HJ74
Molecular weight:: 48357.0

Reactions

L-Arginine + Glycine → Ornithine + Guanidoacetic acid	details
Glycine + L-Arginine → Guanidoacetic acid + Orotidylic acid	details

Showing metabocard for Guanidoacetic acid (BMDB0000128)

Structure for BMDB0000128 (Guanidoacetic acid)

Enzymes

Reactions

Reactions