Cannabis Compound Database: Showing Compound Card for 4-Guanidinobutanoic acid (CDB004959)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Created at

2020-04-17 18:54:39 UTC

Updated at

2020-12-07 19:11:22 UTC

CannabisDB ID

CDB004959

Secondary Accession Numbers

Not Available

Cannabis Compound 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 very strong basic compound (based on its pKa). 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. The 4-guanidino derivative of butanoic acid. 4-Guanidinobutanoic 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
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

Chemical Formula

C₅H₁₁N₃O₂

Average Molecular Weight

145.16

Monoisotopic Molecular Weight

145.0851

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 )

Ontology

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Prostate

Subcellular:

Cytoplasm

Biofluid and excreta:

Physical Properties

State

Solid

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	-1.5	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

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	4-Guanidinobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9000000000-33270c51eae32ab986ff	Spectrum
Predicted GC-MS	4-Guanidinobutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9300000000-6b386451847864ccb5a6	Spectrum
Predicted GC-MS	4-Guanidinobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Guanidinobutanoic acid, non-derivatized, 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, Positive (Annotated)	splash10-0002-2900000000-fde97cd959d0a824fb1a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-7d6981f3d74ac35fbae3	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052r-9000000000-566db10c9a42f3463f73	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-9133b9248cec58ba4611	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-839146a1223d81fcfe1e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0ue9-7900000000-e5db002aeb9f842883d4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000x-9000000000-272ecb5c7a854deaabb6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-dcdfb92af31da28b06e6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0900000000-57afcc249d5db66b3faf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000j-9700000000-20d2b0d6d24335aaf532	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-9000000000-a4bb465c44540f709872	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00kr-9000000000-2803a79b84b073387a24	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0007-9000000000-05ad8804b2be6f14b017	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-9133b9248cec58ba4611	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-839146a1223d81fcfe1e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0ue9-7900000000-e5db002aeb9f842883d4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000x-9000000000-272ecb5c7a854deaabb6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-dcdfb92af31da28b06e6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-7f59dfb80b806d284f40	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2900000000-11fd478790c658cfaec3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0iki-9400000000-483819543e16e57ade03	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-103ac42d2587c5c731b9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udl-3900000000-13045d3e8ab033475c4f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9500000000-087a77898c3c7b51800e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-bb81f668fad53eb8c20b	2016-09-12	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

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Glycine amidinotransferase, mitochondrial	GATM	15q21.1	P50440	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0003464

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

General References

Not Available

Enzymes

Enzyme Details

1. 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. May be involved in the response to heart failure by elevating local creatine synthesis.
Gene Name:: GATM
Uniprot ID:: P50440
Molecular weight:: 48455.01

Showing Compound Card for 4-Guanidinobutanoic acid (CDB004959)

Structure for CDB004959 (4-Guanidinobutanoic acid)

Enzymes