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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2014-10-08 15:56:29 UTC
Update Date2020-02-26 19:17:41 UTC
HMDB IDHMDB0061880
Secondary Accession Numbers
  • HMDB61880
Metabolite Identification
Common NameN-Acetyl-beta-alanine
DescriptionN-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 a very strong basic compound (based on its pKa). N-Acetyl-beta-alanine exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1573765392
Synonyms
ValueSource
3-(Acetylamino)propanoic acidChEBI
3-(Acetylamino)propanoateGenerator
N-Acetyl-b-alanineGenerator
N-Acetyl-β-alanineGenerator
3-(Acetylamino)propionic acidHMDB
3-Acetamidopropanoic acidHMDB
3-Acetamidopropionic acidHMDB
Acetyl-beta-alanineHMDB
Acetyl-β-alanineHMDB
N-Acetyl-3-aminopropanoic acidHMDB
N-Acetyl-3-aminopropionic acidHMDB
N-Acetyl-beta-alanineHMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name3-acetamidopropanoic acid
Traditional NameN-acetyl-β-alanine
CAS Registry Number3025-95-4
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 KeyLJLLAWRMBZNPMO-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.6 g/LALOGPS
logP10(-0.74) g/LALOGPS
logP10(-1.1) g/LChemAxon
logS10(-0.67) g/LALOGPS
pKa (Strongest Acidic)4.34ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.15 m³·mol⁻¹ChemAxon
Polarizability12.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.10731661259
DarkChem[M-H]-121.27931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetyl-beta-alanineCC(=O)NCCC(O)=O2259.2Standard polar33892256
N-Acetyl-beta-alanineCC(=O)NCCC(O)=O1405.2Standard non polar33892256
N-Acetyl-beta-alanineCC(=O)NCCC(O)=O1409.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyl-beta-alanine,1TMS,isomer #1CC(=O)NCCC(=O)O[Si](C)(C)C1388.4Semi standard non polar33892256
N-Acetyl-beta-alanine,1TMS,isomer #2CC(=O)N(CCC(=O)O)[Si](C)(C)C1417.5Semi standard non polar33892256
N-Acetyl-beta-alanine,2TMS,isomer #1CC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C1441.1Semi standard non polar33892256
N-Acetyl-beta-alanine,2TMS,isomer #1CC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C1486.3Standard non polar33892256
N-Acetyl-beta-alanine,2TMS,isomer #1CC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C1594.4Standard polar33892256
N-Acetyl-beta-alanine,1TBDMS,isomer #1CC(=O)NCCC(=O)O[Si](C)(C)C(C)(C)C1643.0Semi standard non polar33892256
N-Acetyl-beta-alanine,1TBDMS,isomer #2CC(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C1615.1Semi standard non polar33892256
N-Acetyl-beta-alanine,2TBDMS,isomer #1CC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1886.9Semi standard non polar33892256
N-Acetyl-beta-alanine,2TBDMS,isomer #1CC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1923.3Standard non polar33892256
N-Acetyl-beta-alanine,2TBDMS,isomer #1CC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1864.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-beta-alanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-f51eb7f132c21dd4983b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-beta-alanine GC-MS (2 TMS) - 70eV, Positivesplash10-00du-9520000000-a868a4d37da9c8cc3ff02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-beta-alanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-beta-alanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 10V, Positive-QTOFsplash10-03k9-7900000000-e63e2d210479d3d853922017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 20V, Positive-QTOFsplash10-00di-9000000000-ddd345f2912ae959783b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 40V, Positive-QTOFsplash10-00fu-9000000000-b6c49c2f8a7545e1935a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 10V, Negative-QTOFsplash10-001i-4900000000-2e37b0db9ab16ad6b4202017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 20V, Negative-QTOFsplash10-000i-9300000000-38962124713aa1c40d0c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 40V, Negative-QTOFsplash10-052f-9000000000-f287dc67dccc990a68a52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 10V, Negative-QTOFsplash10-000i-9000000000-acb26fcb87dcbdf6ba932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 20V, Negative-QTOFsplash10-0a4i-9000000000-4b824ce691fac50e13d42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 40V, Negative-QTOFsplash10-0006-9000000000-f92dcc87e9e245d430f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 10V, Positive-QTOFsplash10-00dl-9000000000-626c84835399415a5c5a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 20V, Positive-QTOFsplash10-00di-9000000000-656385a9629aae802dbe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-beta-alanine 40V, Positive-QTOFsplash10-0006-9000000000-65945af8e71870829fc12021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.151 +/- 0.335 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.199 +/- 0.152 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.214 +/- 0.154 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.299 +/- 0.141 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID68881
KEGG Compound IDC01073
BioCyc IDCPD-580
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76406
PDB IDNot Available
ChEBI ID16682
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Wikipedia [Link]
  9. Ronald Kramer, Alexander Nikolaidis, 'N-Acetyl Beta Alanine Methods of Use.' U.S. Patent US20120264826, issued October 18, 2012. [Link]