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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 07:07:14 UTC

Update Date

2021-09-14 15:20:04 UTC

HMDB ID

HMDB0003911

Secondary Accession Numbers

HMDB0000485
HMDB00485
HMDB03911

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. Beta-ureidopropionase deficiency is an inborn error of pyrimidine degradation associated with neurological abnormalities (OMIM 606673 ). 3-Aminoisobutanoic acid is a potentially toxic compound.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 679461)

Organ

Placenta (HMDB: HMDB0003911)

Excreta

Biofluid or Excreta

Urine (PMID: 679461)
Feces (PMID: 25486321)

Cellular substructure

Cytoplasm (HMDB: HMDB0003911)
Membrane (HMDB: HMDB0003911)

Source

Endogenous

Endogenous (HMDB: HMDB0003911)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Role

Biological role

Metabolite (HMDB: HMDB0003911)
Metabolite (HMDB: HMDB0003911)

Industrial application

Pharmaceutical industry

Biomarker

Aldehyde dehydrogenase deficiency (MarkerDB: MDB00000435)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	124.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002159

Predicted Molecular Properties

Property	Value	Source
Water Solubility	367 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	120.281	31661259
DarkChem	[M-H]-	114.962	31661259
DeepCCS	[M+H]+	128.587	30932474
DeepCCS	[M-H]-	125.789	30932474
DeepCCS	[M-2H]-	162.283	30932474
DeepCCS	[M+Na]+	136.839	30932474
AllCCS	[M+H]+	126.7	32859911
AllCCS	[M+H-H2O]+	122.5	32859911
AllCCS	[M+NH4]+	130.7	32859911
AllCCS	[M+Na]+	131.9	32859911
AllCCS	[M-H]-	124.7	32859911
AllCCS	[M+Na-2H]-	128.7	32859911
AllCCS	[M+HCOO]-	133.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Aminoisobutanoic acid	CC(CN)C(O)=O	2017.0	Standard polar	33892256
3-Aminoisobutanoic acid	CC(CN)C(O)=O	993.6	Standard non polar	33892256
3-Aminoisobutanoic acid	CC(CN)C(O)=O	1033.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Aminoisobutanoic acid,1TMS,isomer #1	CC(CN)C(=O)O[Si](C)(C)C	1038.5	Semi standard non polar	33892256
3-Aminoisobutanoic acid,1TMS,isomer #2	CC(CN[Si](C)(C)C)C(=O)O	1196.0	Semi standard non polar	33892256
3-Aminoisobutanoic acid,2TMS,isomer #1	CC(CN[Si](C)(C)C)C(=O)O[Si](C)(C)C	1217.1	Semi standard non polar	33892256
3-Aminoisobutanoic acid,2TMS,isomer #1	CC(CN[Si](C)(C)C)C(=O)O[Si](C)(C)C	1210.6	Standard non polar	33892256
3-Aminoisobutanoic acid,2TMS,isomer #1	CC(CN[Si](C)(C)C)C(=O)O[Si](C)(C)C	1301.8	Standard polar	33892256
3-Aminoisobutanoic acid,2TMS,isomer #2	CC(CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1403.7	Semi standard non polar	33892256
3-Aminoisobutanoic acid,2TMS,isomer #2	CC(CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1338.4	Standard non polar	33892256
3-Aminoisobutanoic acid,2TMS,isomer #2	CC(CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1610.0	Standard polar	33892256
3-Aminoisobutanoic acid,3TMS,isomer #1	CC(CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1463.0	Semi standard non polar	33892256
3-Aminoisobutanoic acid,3TMS,isomer #1	CC(CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1392.4	Standard non polar	33892256
3-Aminoisobutanoic acid,3TMS,isomer #1	CC(CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1326.5	Standard polar	33892256
3-Aminoisobutanoic acid,1TBDMS,isomer #1	CC(CN)C(=O)O[Si](C)(C)C(C)(C)C	1275.0	Semi standard non polar	33892256
3-Aminoisobutanoic acid,1TBDMS,isomer #2	CC(CN[Si](C)(C)C(C)(C)C)C(=O)O	1442.6	Semi standard non polar	33892256
3-Aminoisobutanoic acid,2TBDMS,isomer #1	CC(CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1656.6	Semi standard non polar	33892256
3-Aminoisobutanoic acid,2TBDMS,isomer #1	CC(CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1654.2	Standard non polar	33892256
3-Aminoisobutanoic acid,2TBDMS,isomer #1	CC(CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1609.4	Standard polar	33892256
3-Aminoisobutanoic acid,2TBDMS,isomer #2	CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	1817.8	Semi standard non polar	33892256
3-Aminoisobutanoic acid,2TBDMS,isomer #2	CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	1743.2	Standard non polar	33892256
3-Aminoisobutanoic acid,2TBDMS,isomer #2	CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	1783.3	Standard polar	33892256
3-Aminoisobutanoic acid,3TBDMS,isomer #1	CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2081.9	Semi standard non polar	33892256
3-Aminoisobutanoic acid,3TBDMS,isomer #1	CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2039.4	Standard non polar	33892256
3-Aminoisobutanoic acid,3TBDMS,isomer #1	CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1751.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (1 TMS)	splash10-001i-3900000000-9d996f1ef303093bc6f2	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (2 TMS)	splash10-0udi-1900000000-599e217ab2fffbcaedcf	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (3 TMS)	splash10-00di-2920000000-235394017181e4a1ccc4	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (Non-derivatized)	splash10-00di-2920000000-235394017181e4a1ccc4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (Non-derivatized)	splash10-001i-3900000000-9d996f1ef303093bc6f2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (Non-derivatized)	splash10-0udi-1900000000-599e217ab2fffbcaedcf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Aminoisobutanoic acid GC-EI-TOF (Non-derivatized)	splash10-00dr-2900000000-83730a256456aac8055a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Aminoisobutanoic acid GC-EI-TOF (Non-derivatized)	splash10-0udi-0900000000-ecf6ec14beb319448103	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-89dae4e73d997d89e2e6	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00ar-9200000000-0eb92539979a9fa36dbd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Aminoisobutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-9200000000-1212facd6e8f1c4ede25	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0udi-6900000000-8b7d740c75c426976897	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0udi-4900000000-68b30ab5196763854bfb	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0udr-5900000000-d8bec01eb9aa047f87d0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0udi-2900000000-d13f4bc606699ca79bda	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid LC-ESI-QTOF , negative-QTOF	splash10-0udi-2900000000-d13f4bc606699ca79bda	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid , negative-QTOF	splash10-0uk9-5900000000-7eb5bc6532d9dac5e48f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid LC-ESI-QTOF , positive-QTOF	splash10-0udr-5900000000-d8bec01eb9aa047f87d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid , positive-QTOF	splash10-0udr-9600000000-62b406ac77af506e283f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-51dcbe7a91ec6bab7de7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 10V, Positive-QTOF	splash10-052r-9100000000-436a48cfb190f66f3cfd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 20V, Positive-QTOF	splash10-0a4i-9000000000-c08aec8a984928aab1fe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 35V, Positive-QTOF	splash10-0udr-9600000000-ad7d786f0ec8c44f3fc0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 35V, Positive-QTOF	splash10-0a4i-9000000000-807636fd22c8a825cf99	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 40V, Positive-QTOF	splash10-0005-9000000000-7b1d59b93a2cf2e3d227	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 10V, Positive-QTOF	splash10-0a4r-9000000000-76fac621e514a8431dde	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 20V, Positive-QTOF	splash10-0a4i-9000000000-6741b7945eaeb59dabe7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 40V, Positive-QTOF	splash10-0006-9000000000-ee2e36c82cc2d0055dd9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 10V, Negative-QTOF	splash10-0uk9-6900000000-e732000e724d2d12a42f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 10V, Positive-QTOF	splash10-0f79-9400000000-e80e2eb321cf19f4e299	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 20V, Positive-QTOF	splash10-000f-9000000000-9649dec1f6afdd5b12c6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 40V, Positive-QTOF	splash10-0006-9000000000-aaf9fc6ded63400c1d6d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 10V, Negative-QTOF	splash10-0udi-2900000000-6f58da61e2ae030dbbad	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 20V, Negative-QTOF	splash10-0zfr-9600000000-ba32a8e8fca536c36023	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Aminoisobutanoic acid 40V, Negative-QTOF	splash10-0a4l-9000000000-e756dcf352426858cb71	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Pyrimidine metabolism	Not Available
Beta Ureidopropionase Deficiency		Not Available
UMP Synthase Deficiency (Orotic Aciduria)		Not Available
Dihydropyrimidinase Deficiency		Not Available
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.8-4.5 uM	Newborn (0-30 days old)	Not Specified	Normal	3939535	details
Blood	Detected and Quantified	1.03 +/- 0.34 uM	Adult (>18 years old)	Male	Normal	679461	details
Blood	Detected and Quantified	0.75 +/- 0.33 uM	Adult (>18 years old)	Female	Normal	679461	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	2.71-57.80 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	300-390 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details
Urine	Detected and Quantified	3.6-13 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	5.5 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	1.24-32.35 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	9.73 +/- 9.20 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	7.20 +/- 6.73 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	34.288 +/- 32.202 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	2.91-116.43 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected and Quantified	<34.048 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.04-354.79 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	4.3-8.5 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	6.81 +/- 2.82 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15992788	details
Urine	Detected and Quantified	25.8 (1.4-155.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	<110.86 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	1.70-117.53 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	25.9 (2.2-140.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	30 +/- 6 uM	Newborn (0-30 days old)	Male	Methylmalonate semialdehyde dehydrogenase deficiency	3939535	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	60.338 +/- 80.333 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	248.732 umol/mmol creatinine	Children (1-13 years old)	Male	D-Lactic Acidosis	832430	details

Associated Disorders and Diseases

Disease References

Methylmalonate semialdehyde dehydrogenase deficiency
Pollitt RJ, Green A, Smith R: Excessive excretion of beta-alanine and of 3-hydroxypropionic, R- and S-3-aminoisobutyric, R- and S-3-hydroxyisobutyric and S-2-(hydroxymethyl)butyric acids probably due to a defect in the metabolism of the corresponding malonic semialdehydes. J Inherit Metab Dis. 1985;8(2):75-9. [PubMed:3939535 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
D-Lactic Acidosis
Duran M, Van Biervliet JP, Kamerling JP, Wadman SK: D-lactic aciduria, an inborn error of metabolism? Clin Chim Acta. 1977 Feb 1;74(3):297-300. [PubMed:832430 ]

Associated OMIM IDs

614105 (Methylmalonate semialdehyde dehydrogenase deficiency)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)
245450 (D-Lactic Acidosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023248

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

3-Aminoisobutyric_acid

METLIN ID

5472

PubChem Compound

64956

PDB ID

Not Available

ChEBI ID

27389

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000435

Good Scents ID

Not Available

References

Synthesis Reference

Balenovic, K.; Jambresic, I.; Ranogajec, I. Preparation of b-aminoisobutyric acid from glycine via the Wolff rearrangement of diazoethyl ketones. Croatica Chemica Acta (1957), 29 87-92.

Material Safety Data Sheet (MSDS)

Not Available

General References

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Fornai M, Blandizzi C, Colucci R, Antonioli L, Bernardini N, Segnani C, Baragatti B, Barogi S, Berti P, Spisni R, Del Tacca M: Role of cyclooxygenases 1 and 2 in the modulation of neuromuscular functions in the distal colon of humans and mice. Gut. 2005 May;54(5):608-16. [PubMed:15831902 ]
Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
Kuo KC, Cole TF, Gehrke CW, Waalkes TP, Borek E: Dual-column cation-exchange chromatographic method for beta-aminoisobutyric acid and beta-alanine in biological samples. Clin Chem. 1978 Aug;24(8):1373-80. [PubMed:679461 ]
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Nelson CP, Gupta P, Napier CM, Nahorski SR, Challiss RA: Functional selectivity of muscarinic receptor antagonists for inhibition of M3-mediated phosphoinositide responses in guinea pig urinary bladder and submandibular salivary gland. J Pharmacol Exp Ther. 2004 Sep;310(3):1255-65. Epub 2004 May 12. [PubMed:15140916 ]
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Morgan CJ, Friedmann PS, Church MK, Clough GF: Cutaneous microdialysis as a novel means of continuously stimulating eccrine sweat glands in vivo. J Invest Dermatol. 2006 Jun;126(6):1220-5. [PubMed:16470172 ]
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Hu J, DeChon J, Yan KC, Liu Q, Hu G, Wu J: Iptakalim inhibits nicotinic acetylcholine receptor-mediated currents in dopamine neurons acutely dissociated from rat substantia nigra pars compacta. Neurosci Lett. 2006 Jul 31;403(1-2):57-62. Epub 2006 May 26. [PubMed:16730119 ]
Hammer RH, Wu W, Sastry JS, Bodor N: Short acting soft mydriatics. Curr Eye Res. 1991 Jun;10(6):565-70. [PubMed:1893772 ]
Salminen L: Review: systemic absorption of topically applied ocular drugs in humans. J Ocul Pharmacol. 1990 Fall;6(3):243-9. [PubMed:2290070 ]
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Foster WM, Bergofsky EH: Airway mucus membrane: effects of beta-adrenergic and anticholinergic stimulation. Am J Med. 1986 Nov 14;81(5A):28-35. [PubMed:2878612 ]
Kanto J, Scheinin M: Placental and blood-CSF transfer of orally administered diazepam in the same person. Pharmacol Toxicol. 1987 Jul;61(1):72-4. [PubMed:3114732 ]
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Enzymes

Enzyme Details

1. Beta-ureidopropionase

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
Specific function:: Converts N-carbamyl-beta-aminoisobutyric acid and N-carbamyl-beta-alanine to, respectively, beta-aminoisobutyric acid and beta-alanine, ammonia and carbon dioxide.
Gene Name:: UPB1
Uniprot ID:: Q9UBR1
Molecular weight:: 43165.705

Reactions

Ureidoisobutyric acid + Water → 3-Aminoisobutanoic acid + Carbon dioxide + Ammonia	details

Showing metabocard for 3-Aminoisobutanoic acid (HMDB0003911)

MOL for HMDB0003911 (3-Aminoisobutanoic acid)

3D MOL for HMDB0003911 (3-Aminoisobutanoic acid)

3D SDF for HMDB0003911 (3-Aminoisobutanoic acid)

3D-SDF for HMDB0003911 (3-Aminoisobutanoic acid)

PDB for HMDB0003911 (3-Aminoisobutanoic acid)

3D PDB for HMDB0003911 (3-Aminoisobutanoic acid)

SMILES for HMDB0003911 (3-Aminoisobutanoic acid)

INCHI for HMDB0003911 (3-Aminoisobutanoic acid)

Structure for HMDB0003911 (3-Aminoisobutanoic acid)

3D Structure for HMDB0003911 (3-Aminoisobutanoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions