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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2014-10-08 15:56:29 UTC

Update Date

2022-09-22 18:34:29 UTC

HMDB ID

HMDB0061880

Secondary Accession Numbers

HMDB61880

Metabolite Identification

Common Name

N-Acetyl-beta-alanine

Description

N-Acetyl-beta-alanine, also known as 3-(acetylamino)propanoate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. N-Acetyl-beta-alanine is the N-acetyl derivative of beta-alanine. It is therefore also classified as an N-acetyl-amino acid and a beta-alanine derivative. It is a substrate for the enzyme called N-acetyl-beta-alanine deacetylase, which converts N-acetyl-beta-alanine into acetate and beta alanine (https://doi.org/10.1016/0005-2744(68)90220-9). N-Acetyl-beta-alanine has also been found in coffee (PMID: 31582163 ). It appears that N-Acetyl-beta-alanine exists in all living organisms, ranging from bacteria to plants to humans.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(Acetylamino)propanoic acid	ChEBI
3-(Acetylamino)propanoate	Generator
N-Acetyl-b-alanine	Generator
N-Acetyl-β-alanine	Generator
3-(Acetylamino)propionic acid	HMDB
3-Acetamidopropanoic acid	HMDB
3-Acetamidopropionic acid	HMDB
Acetyl-beta-alanine	HMDB
Acetyl-β-alanine	HMDB
N-Acetyl-3-aminopropanoic acid	HMDB
N-Acetyl-3-aminopropionic acid	HMDB
N-Acetyl-beta-alanine	HMDB

Chemical Formula

C₅H₉NO₃

Average Molecular Weight

131.1299

Monoisotopic Molecular Weight

131.058243159

IUPAC Name

3-acetamidopropanoic acid

Traditional Name

N-acetyl-β-alanine

CAS Registry Number

3025-95-4

SMILES

CC(=O)NCCC(O)=O

InChI Identifier

InChI=1S/C5H9NO3/c1-4(7)6-3-2-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)

InChI Key

LJLLAWRMBZNPMO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

beta-alanine derivative (CHEBI:16682 )
N-acetyl-amino acid (CHEBI:16682 )

Ontology

Not Available

Physical Properties

State

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.6 g/L	ALOGPS
logP	-0.74	ALOGPS
logP	-1.1	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.15 m³·mol⁻¹	ChemAxon
Polarizability	12.75 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]+	128.107	31661259
DarkChem	[M-H]-	121.279	31661259
DeepCCS	[M+H]+	128.556	30932474
DeepCCS	[M-H]-	125.635	30932474
DeepCCS	[M-2H]-	162.046	30932474
DeepCCS	[M+Na]+	137.12	30932474
AllCCS	[M+H]+	130.3	32859911
AllCCS	[M+H-H2O]+	126.2	32859911
AllCCS	[M+NH4]+	134.1	32859911
AllCCS	[M+Na]+	135.2	32859911
AllCCS	[M-H]-	127.4	32859911
AllCCS	[M+Na-2H]-	130.1	32859911
AllCCS	[M+HCOO]-	133.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-beta-alanine	CC(=O)NCCC(O)=O	2259.2	Standard polar	33892256
N-Acetyl-beta-alanine	CC(=O)NCCC(O)=O	1405.2	Standard non polar	33892256
N-Acetyl-beta-alanine	CC(=O)NCCC(O)=O	1409.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-beta-alanine,1TMS,isomer #1	CC(=O)NCCC(=O)O[Si](C)(C)C	1388.4	Semi standard non polar	33892256
N-Acetyl-beta-alanine,1TMS,isomer #2	CC(=O)N(CCC(=O)O)[Si](C)(C)C	1417.5	Semi standard non polar	33892256
N-Acetyl-beta-alanine,2TMS,isomer #1	CC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1441.1	Semi standard non polar	33892256
N-Acetyl-beta-alanine,2TMS,isomer #1	CC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1486.3	Standard non polar	33892256
N-Acetyl-beta-alanine,2TMS,isomer #1	CC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1594.4	Standard polar	33892256
N-Acetyl-beta-alanine,1TBDMS,isomer #1	CC(=O)NCCC(=O)O[Si](C)(C)C(C)(C)C	1643.0	Semi standard non polar	33892256
N-Acetyl-beta-alanine,1TBDMS,isomer #2	CC(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C	1615.1	Semi standard non polar	33892256
N-Acetyl-beta-alanine,2TBDMS,isomer #1	CC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1886.9	Semi standard non polar	33892256
N-Acetyl-beta-alanine,2TBDMS,isomer #1	CC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1923.3	Standard non polar	33892256
N-Acetyl-beta-alanine,2TBDMS,isomer #1	CC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1864.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-beta-alanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-f51eb7f132c21dd4983b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-beta-alanine GC-MS (2 TMS) - 70eV, Positive	splash10-00du-9520000000-a868a4d37da9c8cc3ff0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-beta-alanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-beta-alanine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 10V, Positive-QTOF	splash10-03k9-7900000000-e63e2d210479d3d85392	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 20V, Positive-QTOF	splash10-00di-9000000000-ddd345f2912ae959783b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 40V, Positive-QTOF	splash10-00fu-9000000000-b6c49c2f8a7545e1935a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 10V, Negative-QTOF	splash10-001i-4900000000-2e37b0db9ab16ad6b420	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 20V, Negative-QTOF	splash10-000i-9300000000-38962124713aa1c40d0c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 40V, Negative-QTOF	splash10-052f-9000000000-f287dc67dccc990a68a5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 10V, Negative-QTOF	splash10-000i-9000000000-acb26fcb87dcbdf6ba93	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 20V, Negative-QTOF	splash10-0a4i-9000000000-4b824ce691fac50e13d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 40V, Negative-QTOF	splash10-0006-9000000000-f92dcc87e9e245d430f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 10V, Positive-QTOF	splash10-00dl-9000000000-626c84835399415a5c5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 20V, Positive-QTOF	splash10-00di-9000000000-656385a9629aae802dbe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 40V, Positive-QTOF	splash10-0006-9000000000-65945af8e71870829fc1	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	0.151 +/- 0.335 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.199 +/- 0.152 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.214 +/- 0.154 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.299 +/- 0.141 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

68881

KEGG Compound ID

C01073

BioCyc ID

CPD-580

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76406

PDB ID

Not Available

ChEBI ID

16682

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Guszczynski T, Bednorz R, Morawska Z: [Activity of alanine aminopeptidase, beta-glucuronidase and N-acetyl-beta-d-glucosaminidase in urine of children with nephrotic syndrome]. Pol Tyg Lek. 1991 Oct 7-21;46(40-42):753-4. [PubMed:1688276 ]
Strigini F, Melis GB, Gasperini M, Ronca G, Palmieri L, Fioretti P: Urinary excretion of N-acetyl-beta-D-glucosaminidase and alanine aminopeptidase during pregnancy. Int J Gynaecol Obstet. 1989 Jan;28(1):9-12. [PubMed:2565837 ]
Hsu WS, Kao JT, Chen JS: Clinical significance of urinary N-acetyl-beta-D-glucosaminidase and alanine aminopeptidase. Taiwan Yi Xue Hui Za Zhi. 1989 Apr;88(4):407-9. [PubMed:2571671 ]
Mueller PW, MacNeil ML, Steinberg KK: Stabilization of alanine aminopeptidase, gamma glutamyltranspeptidase, and N-acetyl-beta-D-glucosaminidase activity in normal urines. Arch Environ Contam Toxicol. 1986 Jul;15(4):343-7. [PubMed:2874775 ]
Diener U, Knoll E, Ratge D, Langer B, Wisser H: Urinary excretion of alanine-aminopeptidase and N-acetyl-beta-D-glucosaminidase during sequential combination chemotherapy. J Clin Chem Clin Biochem. 1982 Sep;20(9):615-9. [PubMed:6183389 ]
Holtje JV, Kopp U, Ursinus A, Wiedemann B: The negative regulator of beta-lactamase induction AmpD is a N-acetyl-anhydromuramyl-L-alanine amidase. FEMS Microbiol Lett. 1994 Sep 15;122(1-2):159-64. [PubMed:7958768 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Desmarchelier A, Hamel J, Delatour T: Sources of overestimation in the analysis of acrylamide-in coffee by liquid chromatography mass spectrometry. J Chromatogr A. 2020 Jan 11;1610:460566. doi: 10.1016/j.chroma.2019.460566. Epub 2019 Sep 23. [PubMed:31582163 ]
Wikipedia [Link]
Ronald Kramer, Alexander Nikolaidis, 'N-Acetyl Beta Alanine Methods of Use.' U.S. Patent US20120264826, issued October 18, 2012. [Link]

Showing metabocard for N-Acetyl-beta-alanine (HMDB0061880)

MOL for HMDB0061880 (N-Acetyl-beta-alanine)

3D MOL for HMDB0061880 (N-Acetyl-beta-alanine)

3D SDF for HMDB0061880 (N-Acetyl-beta-alanine)

3D-SDF for HMDB0061880 (N-Acetyl-beta-alanine)

PDB for HMDB0061880 (N-Acetyl-beta-alanine)

3D PDB for HMDB0061880 (N-Acetyl-beta-alanine)

SMILES for HMDB0061880 (N-Acetyl-beta-alanine)

INCHI for HMDB0061880 (N-Acetyl-beta-alanine)

Structure for HMDB0061880 (N-Acetyl-beta-alanine)

3D Structure for HMDB0061880 (N-Acetyl-beta-alanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra