ChemFOnt: Showing chemical card for gamma-Guanidino-N-butyric acid (CFc000333397)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:27 UTC

Chemfont ID

CFc000333397

Molecule Identification

Common Name

gamma-Guanidino-N-butyric acid

Definition

4-guanidinobutanoic acid, also known as gamma-guanidinobutyrate or 4-(carbamimidamido)butanoate, belongs to gamma amino acids and derivatives class of compounds. Those are amino acids having a (-NH2) group attached to the gamma carbon atom. 4-guanidinobutanoic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 4-guanidinobutanoic acid can be found in apple, french plantain, and loquat, which makes 4-guanidinobutanoic acid a potential biomarker for the consumption of these food products. 4-guanidinobutanoic acid can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as in human prostate tissue. 4-guanidinobutanoic acid exists in all eukaryotes, ranging from yeast to humans. Moreover, 4-guanidinobutanoic acid is found to be associated with cirrhosis.

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

145.1597

Monoisotopic Molecular Weight

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

Exogenous (HMDB: HMDB0003464)

Food

Fruit

Tropical fruit

French plantain (FooDB: FOOD00436)

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Not Available

Physical Properties

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