Livestock Metabolome Database: Showing metabocard for 3-Aminoisobutanoic acid (LMDB00441)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:49:56 UTC

Update Date

2016-07-20 21:01:05 UTC

Lmdb

LMDB00441

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Aminoisobutanoic acid

Description

3-Aminoisobutanoic acid, also known as b-aminoisobutyrate or 2-methyl-beta-alanine, belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. 3-Aminoisobutanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Aminoisobutanoic acid exists in all eukaryotes, ranging from yeast to humans. 3-aminoisobutanoic acid can be biosynthesized from ureidoisobutyric acid; which is mediated by the enzyme Beta-ureidopropionase. In humans, 3-aminoisobutanoic acid is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, 3-Aminoisobutanoic acid has been detected, but not quantified in, milk (cow). This could make 3-aminoisobutanoic acid a potential biomarker for the consumption of these foods. 3-Aminoisobutanoic acid is a potentially toxic compound. A beta-amino-acid that is isobutyric acid in which one of the methyl hydrogens is substituted by an amino group.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(Aminomethyl)propionic acid	ChEBI
2-Methyl-beta-alanine	ChEBI
3-Amino-2-methylpropanoate	ChEBI
3-Aminoisobutanoate	ChEBI
alpha-Methyl-beta-alanine	ChEBI
BAIB	ChEBI
beta-Aminoisobutyric acid	ChEBI
DL-beta-Aminoisobutyric acid	ChEBI
2-(Aminomethyl)propionate	Generator
2-Methyl-b-alanine	Generator
2-Methyl-β-alanine	Generator
3-Amino-2-methylpropanoic acid	Generator
a-Methyl-b-alanine	Generator
Α-methyl-β-alanine	Generator
b-Aminoisobutyrate	Generator
b-Aminoisobutyric acid	Generator
beta-Aminoisobutyrate	Generator
Β-aminoisobutyrate	Generator
Β-aminoisobutyric acid	Generator
DL-b-Aminoisobutyrate	Generator
DL-b-Aminoisobutyric acid	Generator
DL-beta-Aminoisobutyrate	Generator
DL-Β-aminoisobutyrate	Generator
DL-Β-aminoisobutyric acid	Generator
3-Aminoisobutyric acid	HMDB
(+/-)-3-amino-2-methylpropanoate	HMDB
(+/-)-3-amino-2-methylpropanoic acid	HMDB
(+/-)-3-aminoisobutyric acid	HMDB
(+/-)-b-aminoisobutyric acid	HMDB
(+/-)-beta-aminoisobutyric acid	HMDB
3-Amino-isobutanoate	HMDB
3-Amino-isobutanoic acid	HMDB
DL-2-Methyl-b-alanine	HMDB
DL-2-Methyl-beta-alanine	HMDB
DL-3-Amino-2-methylpropionic acid	HMDB
DL-3-Aminoisobutyric acid	HMDB
3-Aminoisobutyric acid, (+-)-isomer	HMDB
DL-3-Aminoisobutyric acid monohydrate	HMDB
3-Aminoisobutyric acid, (S)-isomer	HMDB
3-Aminoisobutyric acid, tritium-labeled	HMDB
3-Aminoisobutyric acid, (R)-isomer	HMDB
3-Aminoisobutyrate	HMDB
3-Aminoisobutanoic acid	ChEBI

Chemical Formula

C₄H₉NO₂

Average Molecular Weight

103.1198

Monoisotopic Molecular Weight

103.063328537

IUPAC Name

3-amino-2-methylpropanoic acid

Traditional Name

(+)-β-aminoisobutyric acid

CAS Registry Number

144-90-1

SMILES

CC(CN)C(O)=O

InChI Identifier

InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)

InChI Key

QCHPKSFMDHPSNR-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta 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

Beta amino acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

beta-amino acid (CHEBI:27389 )
Other amino acids (C05145 )
Amino fatty acids (LMFA01100054 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	-3	ALOGPS
logP	-2.6	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	10.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.28 m³·mol⁻¹	ChemAxon
Polarizability	10.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-001i-3900000000-9d996f1ef303093bc6f2	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-1900000000-599e217ab2fffbcaedcf	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-2920000000-235394017181e4a1ccc4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-2920000000-235394017181e4a1ccc4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-3900000000-9d996f1ef303093bc6f2	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-1900000000-599e217ab2fffbcaedcf	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-2900000000-83730a256456aac8055a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0900000000-ecf6ec14beb319448103	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-89dae4e73d997d89e2e6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ar-9200000000-0eb92539979a9fa36dbd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9200000000-1212facd6e8f1c4ede25	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-6900000000-8b7d740c75c426976897	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0udi-4900000000-68b30ab5196763854bfb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udr-5900000000-d8bec01eb9aa047f87d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-2900000000-d13f4bc606699ca79bda	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-2900000000-d13f4bc606699ca79bda	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0uk9-5900000000-7eb5bc6532d9dac5e48f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udr-5900000000-d8bec01eb9aa047f87d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udr-9600000000-62b406ac77af506e283f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-51dcbe7a91ec6bab7de7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9100000000-436a48cfb190f66f3cfd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-c08aec8a984928aab1fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udr-9600000000-ad7d786f0ec8c44f3fc0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-9000000000-807636fd22c8a825cf99	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9000000000-7b1d59b93a2cf2e3d227	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-9000000000-76fac621e514a8431dde	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-6741b7945eaeb59dabe7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ee2e36c82cc2d0055dd9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0uk9-6900000000-e732000e724d2d12a42f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-9400000000-e80e2eb321cf19f4e299	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9000000000-9649dec1f6afdd5b12c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-aaf9fc6ded63400c1d6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-6f58da61e2ae030dbbad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-9600000000-ba32a8e8fca536c36023	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-e756dcf352426858cb71	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details