Bovine Metabolome Database: Showing metabocard for Beta-Alanine (BMDB0000056)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:05 UTC

Update Date

2020-06-04 20:29:50 UTC

BMDB ID

BMDB0000056

Secondary Accession Numbers

BMDB00056

Metabolite Identification

Common Name

Beta-Alanine

Description

beta-Alanine, also known as 3-aminopropanoate or bala, 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. beta-Alanine is a very strong basic compound (based on its pKa). beta-Alanine exists in all living species, ranging from bacteria to humans. beta-Alanine is a potentially toxic compound. beta-Alanine, with regard to humans, has been found to be associated with several diseases such as crohn's disease, alzheimer's disease, methylmalonate semialdehyde dehydrogenase deficiency, and frontotemporal dementia; beta-alanine has also been linked to the inborn metabolic disorder dihydropyrimidine dehydrogenase deficiency.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
3-Aminopropanoic acid	ChEBI
3-Aminopropionic acid	ChEBI
BAla	ChEBI
beta-Aminopropionic acid	ChEBI
H-beta-Ala-OH	ChEBI
Omega-aminopropionic acid	ChEBI
3-Aminopropanoate	Kegg
Abufene	Kegg
3-Aminopropionate	Generator
b-Aminopropionate	Generator
b-Aminopropionic acid	Generator
beta-Aminopropionate	Generator
Β-aminopropionate	Generator
Β-aminopropionic acid	Generator
H-b-Ala-OH	Generator
H-Β-ala-OH	Generator
Omega-aminopropionate	Generator
b-Alanine	Generator
Β-alanine	Generator
2-Carboxyethylamine	HMDB
3-Amino-propanoate	HMDB
3-Amino-propanoic acid	HMDB
b-Aminopropanoate	HMDB
b-Aminopropanoic acid	HMDB
beta Alanine	HMDB
beta-Aminopropanoate	HMDB
beta-Aminopropanoic acid	HMDB
3 Aminopropionic acid	HMDB
β-Aminopropanoic acid	PhytoBank
omega-Aminopropanoic acid	PhytoBank
ω-Aminopropanoic acid	PhytoBank
ω-Aminopropionic acid	PhytoBank
beta-Alanine	PhytoBank

Chemical Formula

C₃H₇NO₂

Average Molecular Weight

89.0932

Monoisotopic Molecular Weight

89.047678473

IUPAC Name

3-aminopropanoic acid

Traditional Name

β alanine

CAS Registry Number

107-95-9

SMILES

NCCC(O)=O

InChI Identifier

InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)

InChI Key

UCMIRNVEIXFBKS-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:16958 )
Other amino acids (C00099 )
Biogenic amines (C00099 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	545.0 mg/mL	Not Available
LogP	-3.05	TSAI,RS ET AL. (1991)

Predicted Properties

Property	Value	Source
logP	-3.3	ALOGPS
logP	-3.2	ChemAxon
logS	0.74	ALOGPS
pKa (Strongest Acidic)	4.08	ChemAxon
pKa (Strongest Basic)	10.31	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	20.7 m³·mol⁻¹	ChemAxon
Polarizability	8.62 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-007k-1920000000-9389ee061bd6e9ae3b22	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0fdt-2930000000-5799fddb7fac04d22372	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-006t-1940000000-49f1b7c80f35cbcf102e	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-006t-2920000000-c701f2e5652fa4f35e50	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-8930000000-c4f8138d4cb7f1ea851a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-014i-2900000000-c54f1d5878600393dca7	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-1900000000-2f55a09bba074034dee7	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00ds-2940000000-4192453eaba2cbecf800	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006t-1960000000-665868f9adaa275dbdb3	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-007k-1920000000-9389ee061bd6e9ae3b22	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fdt-2930000000-5799fddb7fac04d22372	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-1940000000-49f1b7c80f35cbcf102e	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-2920000000-c701f2e5652fa4f35e50	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-8930000000-c4f8138d4cb7f1ea851a	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00ds-2940000000-4192453eaba2cbecf800	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-2900000000-c54f1d5878600393dca7	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-1900000000-2f55a09bba074034dee7	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0900000000-efc0822e26bcf842e232	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0072-2920000000-284cff207c712b6698d6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-ad7f96b2c6a1f5183794	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-9700000000-d73baf312b8af27575b3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-61740a52186a51b8543c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-1bdf967935160468d550	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-0ba5264cfc5ec108718b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-61740a52186a51b8543c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-1bdf967935160468d550	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-0ba5264cfc5ec108718b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-1c44f6e35a8ed7d36b09	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-799cbaba87e33fa5afde	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-86d934e6151015ddb810	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00dl-9000000000-c30cc77c93e4ec09265a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000j-9000000000-540a52fcec629c0a0647	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000b-9000000000-531b17f8e16896225186	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-9000000000-c6a2c78d322328400127	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-9000000000-d5f47100c42e7777802e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-e8f43be75c153e5be3cc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-1004-9000100000-ccb09493216d97165c8d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00l7-9230000000-644b1dbe52c5f07e285a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0006-9000000000-ff4a990aa1fb1b7cc33d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-c6a2c78d322328400127	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9000000000-d5f47100c42e7777802e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-e8f43be75c153e5be3cc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-1004-9000100000-ccb09493216d97165c8d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00l7-9230000000-644b1dbe52c5f07e285a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-9000000000-ff4a990aa1fb1b7cc33d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-363393d05fd6a4b82318	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-be815b0a56f225da04d8	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Kidney
Liver
Longissimus Thoracis Muscle
Mammary Gland
Muscle
Pancreas
Placenta
Prostate Tissue
Ruminal Fluid
Semen
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Aspartate Metabolism		Not Available
beta-Alanine Metabolism		Not Available
Histidine Metabolism		Not Available
Pyrimidine Metabolism		Not Available
Propanoate Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	8 +/- 1 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected and Quantified	8.8-9.1 uM	Not Specified	Not Specified	Normal	PMID: 28036059	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected and Quantified	750 +/- 137 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Longissimus Thoracis Muscle	Detected and Quantified	149 +/- 57 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Muscle	Detected and Quantified	84-155 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 30744349	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	3-33 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Ruminal Fluid	Detected and Quantified	72 +/- 38 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29634739	details
Semimembranosus Muscle	Detected and Quantified	122 +/- 37 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	48 +/- 13 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000056

DrugBank ID

DB03107

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16958

References

Synthesis Reference

Buc, Saul R.; Ford, Jared H.; Wise, E. C. Improved synthesis of b-alanine. Journal of the American Chemical Society (1945), 67 92-4.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 4-aminobutyrate aminotransferase, mitochondrial

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine (By similarity).
Gene Name:: ABAT
Uniprot ID:: Q9BGI0
Molecular weight:: 56731.0

Reactions

Beta-Alanine + Oxoglutaric acid → Malonic semialdehyde + L-Glutamic acid	details

Enzyme Details

2. Cytosolic non-specific dipeptidase

General function:: Amino acid transport and metabolism
Specific function:: Hydrolyzes a variety of dipeptides including L-carnosine but has a strong preference for Cys-Gly. Catalyzes the production of N-lactoyl-amino acids from lactate and amino acids by reverse proteolysis.
Gene Name:: CNDP2
Uniprot ID:: Q3ZC84
Molecular weight:: 52655.0

Reactions

Anserine + Water → Beta-Alanine + 3-Methylhistidine	details
Carnosine + Water → Beta-Alanine + L-Histidine	details
Anserine + Water → Beta-Alanine + 1-Methylhistidine	details

Enzyme Details

3. Glutamate decarboxylase 1

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the production of GABA.
Gene Name:: GAD1
Uniprot ID:: Q0VCA1
Molecular weight:: 66784.0

Reactions

L-Aspartic acid → Beta-Alanine + Carbon dioxide	details

Enzyme Details

4. Deaminated glutathione amidase

General function:: Not Available
Specific function:: Catalyzes the hydrolysis of the amide bond in N-(4-oxoglutarate)-L-cysteinylglycine (deaminated glutathione), a metabolite repair reaction to dispose of the harmful deaminated glutathione. Plays a role in cell growth and apoptosis. Has tumor suppressor properties that enhances the apoptotic responsiveness in cancer cells. It is also a negative regulator of primary T-cells.
Gene Name:: NIT1
Uniprot ID:: Q32LH4
Molecular weight:: 36240.0

Reactions

Ureidopropionic acid + Water → Beta-Alanine + Carbon dioxide + Ammonia	details
Ureidopropionic acid + Water → Beta-Alanine + Ammonia + Carbon dioxide	details

Enzyme Details

5. ATP-grasp domain-containing protein

General function:: Not Available
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: A5PJL9
Molecular weight:: 54461.0

Reactions

Adenosine triphosphate + L-Histidine + Beta-Alanine → ADP + Hydrogen phosphate + Carnosine	details
Adenosine triphosphate + 1-Methylhistidine + Beta-Alanine → ADP + Hydrogen phosphate + Anserine	details

Showing metabocard for Beta-Alanine (BMDB0000056)

Structure for BMDB0000056 (Beta-Alanine)

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions