Milk Composition Database: Showing metabocard for 2,4-Diaminobutyric acid (BMDB0062039)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-06-25 21:45:58 UTC

Update Date

2020-05-05 18:40:37 UTC

MCDB ID

BMDB0062039

Secondary Accession Numbers

BMDB62039

Metabolite Identification

Common Name

2,4-Diaminobutyric acid

Description

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.

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 )

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	-4.64	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	1	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fk9-1920000000-4022550ff40c74b94da2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uki-1910000000-34aec762a0d88f0ff2eb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0h00-0920000000-ed1d230736f055292644	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fe0-2900000000-011f7377726e8e3fba20	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0923000000-fcaabed9d8d79390c079	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fk9-1920000000-4022550ff40c74b94da2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uki-1910000000-34aec762a0d88f0ff2eb	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0h00-0920000000-ed1d230736f055292644	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fe0-2900000000-011f7377726e8e3fba20	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0923000000-fcaabed9d8d79390c079	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0089-9000000000-0ff95cc18b5212b1c153	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0uk9-8900000000-25af6f5f252b501941e0	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)	splash10-0udi-5900000000-c2bc7797818665414515	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-86fc81ed1cba676fc615	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-dbbf8294790c9cfa4247	2012-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0v4i-7900000000-ca2dc0489c4a710e50dd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-72113ca7f0d0dd46ad4f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-787cd47720f4158a0201	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-fd55d2abd69c5f1c09cd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-8900000000-d0f5d2df75ce6b002347	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9000000000-da3e8260fa5485a69ab1	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-9700000000-fdbd4f0e5bb81c5569f4	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-880db7b265999a2be6b5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-b2689f286fc18087ebce	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-de9219963e7858b4c55a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-4900000000-2a4facf9f300cca66157	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-d4591f1517185fa3d719	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected but not Quantified	Not Applicable	PMID: 29197344	details
Detected but not Quantified	Not Applicable	PMID: 28306241	details

External Links

HMDB ID

HMDB0002362

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]

Showing metabocard for 2,4-Diaminobutyric acid (BMDB0062039)

Structure for BMDB0062039 (2,4-Diaminobutyric acid)