Livestock Metabolome Database: Showing metabocard for Guanidoacetic acid (LMDB00054)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:41:22 UTC

Update Date

2016-07-20 21:03:10 UTC

Lmdb

LMDB00054

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Guanidoacetic acid

Description

Guanidoacetic acid, also known as guanidinoacetate or N-amidinoglycine, 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 a very strong basic compound (based on its pKa). Guanidoacetic acid exists in all living organisms, ranging from bacteria to humans. Within humans, guanidoacetic acid participates in a number of enzymatic reactions. In particular, guanidoacetic acid and orotidylic acid can be biosynthesized from glycine and L-arginine; which is mediated by the enzyme glycine amidinotransferase, mitochondrial. In addition, guanidoacetic acid and S-adenosylhomocysteine can be converted into S-adenosylmethionine and creatine through its interaction with the enzyme guanidinoacetate N-methyltransferase. In humans, guanidoacetic acid is involved in glycine and serine metabolism. The N-amidino derivative of glycine. Outside of the human body, Guanidoacetic acid has been detected, but not quantified in, apples and loquats. This could make guanidoacetic acid a potential biomarker for the consumption of these foods. 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

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0901000000-4a89fe463d29379e6339	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0911000000-542baca9dcca73225bf0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-0911200000-bb7ea068f193f39c283b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0901000000-4a89fe463d29379e6339	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0911000000-542baca9dcca73225bf0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-0911200000-bb7ea068f193f39c283b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-c703c631a81e400681bd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9700000000-1dae820000c4f9ec1662	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-016r-7900000000-4777d20e1ab29262427e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dl-9000000000-a1b5501bf0f7a9b0489d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-b61a48cf749b57a2c77e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0gk9-7900000000-5ba298286886c1fabdf5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00di-9100000000-a5b77a913821d637210f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-9100000000-a5b77a913821d637210f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gk9-7900000000-5ba298286886c1fabdf5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-6900000000-4d655a894c702bdfdb59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-23d5c2795ed49f043127	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-ae360cd8919c8fbce3ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-93406e2cdb79770abc7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-c6bd00733ea6fa3f6e5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-2667e0007de6a723415e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0100-9400000000-c5561d5ccaf260c048ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0g29-9400000000-421d076c4b6868ca69fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-53db4bf2729a2990a938	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05fu-9000000000-2cad7322e574eb992175	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-01di-9800000000-967331a78fe4a7917408	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-7b281fae734baaa2695d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-1b831140a3071dd98e0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9300000000-b27aea734be08f5d2ddc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9000000000-dea2f28faa5430d7e56f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-9500000000-1ba345c7064e9cb70f9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-6864d4355d3462fbc69f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-1c36299ab8746bbf67a5	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details