MiMeDB: Showing metabocard for 4-guanidinobutanoic acid (MMDBc0033043)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:32:17 UTC

Update Date

2024-04-30 19:59:20 UTC

Metabolite ID

MMDBc0033043

Metabolite Identification

Common Name

4-guanidinobutanoic acid

Description

4-Guanidinobutanoic acid, also known as gamma-guanidinobutyrate or 4-(carbamimidamido)butanoate, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. 4-Guanidinobutanoic acid is a normal metabolite present in low concentrations. 4-Guanidinobutanoic acid exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, 4-Guanidinobutanoic acid has been detected, but not quantified in a few different foods, such as apples, french plantains, and loquats. This could make 4-guanidinobutanoic acid a potential biomarker for the consumption of these foods. Patients with hyperargininemia have an arginase deficiency which leads to blockade of the urea cycle in the last step with several clinical symptoms. Owing to the arginase deficiency this patients accumulate arginine which leads eventually to epileptogenic guanidino compounds (PMID 7752905 ).

Structure

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

Synonyms

Value	Source
4-Guanidinobutanoate	ChEBI
4-Guanidinobutyric acid	ChEBI
gamma-Guanidinobutyrate	ChEBI
gamma-Guanidinobutyric acid	ChEBI
4-Guanidinobutyrate	Generator
g-Guanidinobutyrate	Generator
g-Guanidinobutyric acid	Generator
Γ-guanidinobutyrate	Generator
Γ-guanidinobutyric acid	Generator
4-(Carbamimidamido)butanoate	HMDB
4-(Carbamimidamido)butanoic acid	HMDB
gamma-Guanidinobutyrate, monosodium salt	HMDB
4-[(Aminoiminomethyl)amino]butanoate	HMDB
4-[(Aminoiminomethyl)amino]butanoic acid	HMDB
N-(4-Butanoate)guanidine	HMDB
N-(4-Butanoic acid)guanidine	HMDB
gamma-Guanidinebutyrate	HMDB
gamma-Guanidinebutyric acid	HMDB
Γ-guanidinebutyrate	HMDB
Γ-guanidinebutyric acid	HMDB
4-Guanidinobutanoic acid	Generator

Molecular Formula

C₅H₁₁N₃O₂

Average Mass

145.1597

Monoisotopic Mass

145.085126611

IUPAC Name

4-[(diaminomethylidene)amino]butanoic acid

Traditional Name

4-[(diaminomethylidene)amino]butanoic acid

CAS Registry Number

463-00-3

SMILES

NC(=N)NCCCC(O)=O

InChI Identifier

InChI=1S/C5H11N3O2/c6-5(7)8-3-1-2-4(9)10/h1-3H2,(H,9,10)(H4,6,7,8)

InChI Key

TUHVEAJXIMEOSA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Straight chain fatty acid
Fatty acid
Fatty acyl
Guanidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:15728 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.78 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-2.7	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	12.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	101.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.88 m³·mol⁻¹	ChemAxon
Polarizability	14.71 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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-33270c51eae32ab986ff	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9300000000-6b386451847864ccb5a6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-2900000000-fde97cd959d0a824fb1a	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-7d6981f3d74ac35fbae3	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052r-9000000000-566db10c9a42f3463f73	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-9133b9248cec58ba4611	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-839146a1223d81fcfe1e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0ue9-7900000000-e5db002aeb9f842883d4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000x-9000000000-272ecb5c7a854deaabb6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-dcdfb92af31da28b06e6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0900000000-57afcc249d5db66b3faf	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000j-9700000000-20d2b0d6d24335aaf532	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-9000000000-a4bb465c44540f709872	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00kr-9000000000-2803a79b84b073387a24	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0007-9000000000-05ad8804b2be6f14b017	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-9133b9248cec58ba4611	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-839146a1223d81fcfe1e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0ue9-7900000000-e5db002aeb9f842883d4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000x-9000000000-272ecb5c7a854deaabb6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-dcdfb92af31da28b06e6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-7f59dfb80b806d284f40	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2900000000-11fd478790c658cfaec3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0iki-9400000000-483819543e16e57ade03	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-103ac42d2587c5c731b9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udl-3900000000-13045d3e8ab033475c4f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9500000000-087a77898c3c7b51800e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-bb81f668fad53eb8c20b	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Prostate
Urine

Tissue Locations

Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192122	Glycine amidinotransferase, mitochondrial	Enzyme	P50440	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cirrhosis	Slight Increase	Association	Human Blood	HMDB	7752905
Cirrhosis		Association	Human Urine	HMDB	7752905
Uremia	Increased	Association	Human Blood	HMDB	12675874

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown
Bacteria	Actinobacteria	1
Bacteria	Proteobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Tea		FooDB	31437929
Plant	Tea	Camellia sinensis	FooDB	31437929
Plant	Tea		FooDB	31437929
Plant	Tea		FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.05		0.013	0.09	uM	Adult (>18 years old)	Both	Cirrhosis	HMDB	7752905
Human Urine	Detected and Quantified	1.0	0.8			umol/mmol creatinine	Adult (>18 years old)	Both	Cirrhosis	HMDB	7752905
Human Blood	Detected and Quantified	0.230	0.110			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	<0.0248				uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0125		0	0.025	uM	Adult (>18 years old)	Both	Normal	HMDB	3433275
Human Blood	Detected and Quantified	0.034		0.013	0.055	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	7752905
Human Urine	Detected and Quantified	0.17		0.0	0.37	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18818040
Human Blood	Detected and Quantified	0.21		0.0	0.43	uM	Adult (>18 years old)	Both	Normal	HMDB	18818040
Human Urine	Detected and Quantified	1.3	1.05			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	7752905
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0003464

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005408

KNApSAcK ID

Not Available

Chemspider ID

486

KEGG Compound ID

C01035

BioCyc ID

CPD-592

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6938

PubChem Compound

500

PDB ID

Not Available

ChEBI ID

15728

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. doi: 10.1620/tjem.153.197. [PubMed:3433275 ]
De Deyn PP, Marescau B, Cuykens JJ, Van Gorp L, Lowenthal A, De Potter WP: Guanidino compounds in serum and cerebrospinal fluid of non-dialyzed patients with renal insufficiency. Clin Chim Acta. 1987 Jul 30;167(1):81-8. doi: 10.1016/0009-8981(87)90088-x. [PubMed:3665089 ]
Marescau B, Qureshi IA, De Deyn P, Letarte J, Ryba R, Lowenthal A: Guanidino compounds in plasma, urine and cerebrospinal fluid of hyperargininemic patients during therapy. Clin Chim Acta. 1985 Feb 28;146(1):21-7. doi: 10.1016/0009-8981(85)90120-2. [PubMed:3987036 ]
Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C: Guanidino compounds in serum and urine of cirrhotic patients. Metabolism. 1995 May;44(5):584-8. doi: 10.1016/0026-0495(95)90114-0. [PubMed:7752905 ]
Gatti R, Gioia MG: Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds. J Pharm Biomed Anal. 2006 Sep 11;42(1):11-6. doi: 10.1016/j.jpba.2005.12.035. Epub 2006 Feb 3. [PubMed:16460903 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 4-guanidinobutanoic acid (MMDBc0033043)

MOL for #<Metabolite:0x00005634c0e1b608>

3D MOL for #<Metabolite:0x00005634c0e1b608>

3D SDF for #<Metabolite:0x00005634c0e1b608>

3D-SDF for #<Metabolite:0x00005634c0e1b608>

PDB for #<Metabolite:0x00005634c0e1b608>

3D PDB for #<Metabolite:0x00005634c0e1b608>

SMILES for #<Metabolite:0x00005634c0e1b608>

INCHI for #<Metabolite:0x00005634c0e1b608>

Structure for #<Metabolite:0x00005634c0e1b608>

3D Structure for #<Metabolite:0x00005634c0e1b608>