ChemFOnt: Showing chemical card for 2,4-Diaminobutyric acid (CFc000001592)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:15 UTC

Chemfont ID

CFc000001592

Molecule Identification

Common Name

2,4-Diaminobutyric acid

Definition

2,4-Diaminobutyric acid, also known as 2,4-diaminobutanoate or Dbu, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2,4-Diaminobutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2,4-Diaminobutyric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2,4-Diaminobutyric acid has been detected, but not quantified in cow milk. This could make 2,4-diaminobutyric acid a potential biomarker for the consumption of these foods. 2,4-Diaminobutyric acid is a non-physiological, cationic amino acid analogue that is transported into cells by System A with potent antitumoral activity in vitro against human glioma cells, the result of the pronounced concentrated uptake of DAB in glioma cells to the extent that a cellular lysis could occur due to osmotic reasons.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,4-Diaminobutanoic acid	ChEBI
alpha,gamma-Diaminobutanoic acid	ChEBI
alpha,gamma-Diaminobutyric acid	ChEBI
Dbu	ChEBI
2,4-Diaminobutanoate	Generator
a,g-Diaminobutanoate	Generator
a,g-Diaminobutanoic acid	Generator
alpha,gamma-Diaminobutanoate	Generator
Α,γ-diaminobutanoate	Generator
Α,γ-diaminobutanoic acid	Generator
a,g-Diaminobutyrate	Generator
a,g-Diaminobutyric acid	Generator
alpha,gamma-Diaminobutyrate	Generator
Α,γ-diaminobutyrate	Generator
Α,γ-diaminobutyric acid	Generator
2,4-Diaminobutyrate	Generator
(RS)-2,4-Diaminobutyric acid	HMDB
2,4-diamino-Butanoate	HMDB
2,4-diamino-Butanoic acid	HMDB
2,4-diamino-Butyric acid	HMDB
2,4-diamino-N-Butyric acid	HMDB
DL-2,4-diamino-N-Butyric acid	HMDB
DL-2,4-Diaminobutanoate	HMDB
DL-2,4-Diaminobutanoic acid	HMDB
DL-2,4-Diaminobutyric acid	HMDB
DL-alpha,gamma-Diaminobutyric acid	HMDB
2,4-Diaminobutyric acid dihydrochloride, (+-)-isomer	MeSH, HMDB
2,4-Diaminobutyric acid monohydrochloride, (S)-isomer	MeSH, HMDB
2,4-Diaminobutyric acid, (+)-isomer	MeSH, HMDB
2,4-Diaminobutyric acid, (+-)-isomer	MeSH, HMDB
2,4-Diaminobutyric acid, (R)-isomer	MeSH, HMDB
2,4-Diaminobutyric acid, (S)-isomer	MeSH, HMDB
L-2,4-Diaminobutyric acid	MeSH, HMDB
2,4-Diaminobutyric acid dihydrochloride, (S)-isomer	MeSH, HMDB
2,4-Diaminobutyric acid monohydrochloride, (+-)-isomer	MeSH, HMDB
2,4-Diamino-butyrate	Generator, HMDB
2,4-Diaminobutyric acid	MeSH

Chemical Formula

C₄H₁₀N₂O₂

Average Molecular Weight

118.1344

Monoisotopic Molecular Weight

118.074227574

IUPAC Name

2,4-diaminobutanoic acid

Traditional Name

2,4-diaminobutanoic acid

CAS Registry Number

305-62-4

SMILES

NCCC(N)C(O)=O

InChI Identifier

InChI=1S/C4H10N2O2/c5-2-1-3(6)4(7)8/h3H,1-2,5-6H2,(H,7,8)

InChI Key

OGNSCSPNOLGXSM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

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

Alternative Parents

Substituents

Alpha-amino acid
Amino fatty acid
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:64307 )
diamino acid (CHEBI:64307 )
gamma-amino acid (CHEBI:64307 )
Amino fatty acids (LMFA01100052 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002362)

Excreta

Biofluid or Excreta

Urine (PMID: 21388201)
Feces (PMID: 25486321)

Cellular substructure

Cytoplasm (HMDB: HMDB0002362)

Source

Exogenous

Exogenous (HMDB: HMDB0002362)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Industrial application

Drug (HMDB: HMDB0002362)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	270 g/L	ALOGPS
logP	-3.7	ALOGPS
logP	-4	ChemAxon
logS	0.36	ALOGPS
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	9.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.34 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.56 m³·mol⁻¹	ChemAxon
Polarizability	11.79 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

External Links

HMDB ID

HMDB0002362

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022978

KNApSAcK ID

C00034868

Chemspider ID

457

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

470

PDB ID

Not Available

ChEBI ID

64307

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Talbot, Guy; Gaudry, Roger; Berlinguet, Louis. Synthesis of 4-aminobutyric acid and 2,4-diaminobutyric acid from butyrolactone. Canadian Journal of Chemistry (1958), 36 593-6.

Showing chemical card for 2,4-Diaminobutyric acid (CFc000001592)

MOL for CFc000001592 (2,4-Diaminobutyric acid)

3D MOL for CFc000001592 (2,4-Diaminobutyric acid)

3D SDF for CFc000001592 (2,4-Diaminobutyric acid)

3D-SDF for CFc000001592 (2,4-Diaminobutyric acid)

PDB for CFc000001592 (2,4-Diaminobutyric acid)

3D PDB for CFc000001592 (2,4-Diaminobutyric acid)

SMILES for CFc000001592 (2,4-Diaminobutyric acid)

INCHI for CFc000001592 (2,4-Diaminobutyric acid)

Structure for CFc000001592 (2,4-Diaminobutyric acid)

3D Structure for CFc000001592 (2,4-Diaminobutyric acid)