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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-01-29 12:43:59 UTC
Update Date2023-02-21 17:17:29 UTC
HMDB IDHMDB0011602
Secondary Accession Numbers
  • HMDB11602
Metabolite Identification
Common Name3-Oxoalanine
Description3-Oxoalanine, also known as C-formylglycine or fgly, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 3-Oxoalanine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-oxoalanine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Oxoalanine.
Structure
Data?1676999849
Synonyms
ValueSource
alpha-FormylglycineChEBI
C(alpha)-FormylglycineChEBI
C-FormylglycineChEBI
FGlyChEBI
a-FormylglycineGenerator
Α-formylglycineGenerator
C(a)-FormylglycineGenerator
C(Α)-formylglycineGenerator
2-amino-3-oxo-PropanoateHMDB
2-amino-3-oxo-Propanoic acidHMDB
2-FormylglycineHMDB
3-oxo-(9CI)-alanineHMDB
amino-(8CI)malonaldehydic acidHMDB
L-alpha-FormylglycineMeSH, HMDB
2-amino-3-Oxopropanoic acidMeSH, HMDB
3-oxo-L-AlanineMeSH, HMDB
Chemical FormulaC3H5NO3
Average Molecular Weight103.0767
Monoisotopic Molecular Weight103.026943031
IUPAC Name2-amino-3-oxopropanoic acid
Traditional Nameα-formylglycine
CAS Registry Number5735-66-0
SMILES
NC(C=O)C(O)=O
InChI Identifier
InChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)
InChI KeyXMTCKNXTTXDPJX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • 1,3-dicarbonyl compound
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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 Solubility242 g/LALOGPS
logP-2.8ALOGPS
logP-3.6ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)1.66ChemAxon
pKa (Strongest Basic)7.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.06 m³·mol⁻¹ChemAxon
Polarizability8.59 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]+120.01231661259
DarkChem[M-H]-112.79731661259
DeepCCS[M+H]+126.22330932474
DeepCCS[M-H]-123.42530932474
DeepCCS[M-2H]-159.81830932474
DeepCCS[M+Na]+134.37830932474
AllCCS[M+H]+127.432859911
AllCCS[M+H-H2O]+123.132859911
AllCCS[M+NH4]+131.432859911
AllCCS[M+Na]+132.632859911
AllCCS[M-H]-119.432859911
AllCCS[M+Na-2H]-123.332859911
AllCCS[M+HCOO]-127.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-OxoalanineNC(C=O)C(O)=O1959.4Standard polar33892256
3-OxoalanineNC(C=O)C(O)=O932.0Standard non polar33892256
3-OxoalanineNC(C=O)C(O)=O1486.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Oxoalanine,1TMS,isomer #1C[Si](C)(C)OC(=O)C(N)C=O1122.2Semi standard non polar33892256
3-Oxoalanine,1TMS,isomer #2C[Si](C)(C)OC=C(N)C(=O)O1303.0Semi standard non polar33892256
3-Oxoalanine,1TMS,isomer #3C[Si](C)(C)NC(C=O)C(=O)O1184.1Semi standard non polar33892256
3-Oxoalanine,2TMS,isomer #1C[Si](C)(C)OC=C(N)C(=O)O[Si](C)(C)C1342.4Semi standard non polar33892256
3-Oxoalanine,2TMS,isomer #1C[Si](C)(C)OC=C(N)C(=O)O[Si](C)(C)C1277.3Standard non polar33892256
3-Oxoalanine,2TMS,isomer #1C[Si](C)(C)OC=C(N)C(=O)O[Si](C)(C)C1940.9Standard polar33892256
3-Oxoalanine,2TMS,isomer #2C[Si](C)(C)NC(C=O)C(=O)O[Si](C)(C)C1267.8Semi standard non polar33892256
3-Oxoalanine,2TMS,isomer #2C[Si](C)(C)NC(C=O)C(=O)O[Si](C)(C)C1211.0Standard non polar33892256
3-Oxoalanine,2TMS,isomer #2C[Si](C)(C)NC(C=O)C(=O)O[Si](C)(C)C1478.2Standard polar33892256
3-Oxoalanine,2TMS,isomer #3C[Si](C)(C)NC(=CO[Si](C)(C)C)C(=O)O1453.5Semi standard non polar33892256
3-Oxoalanine,2TMS,isomer #3C[Si](C)(C)NC(=CO[Si](C)(C)C)C(=O)O1379.9Standard non polar33892256
3-Oxoalanine,2TMS,isomer #3C[Si](C)(C)NC(=CO[Si](C)(C)C)C(=O)O1832.0Standard polar33892256
3-Oxoalanine,2TMS,isomer #4C[Si](C)(C)N(C(C=O)C(=O)O)[Si](C)(C)C1433.8Semi standard non polar33892256
3-Oxoalanine,2TMS,isomer #4C[Si](C)(C)N(C(C=O)C(=O)O)[Si](C)(C)C1296.2Standard non polar33892256
3-Oxoalanine,2TMS,isomer #4C[Si](C)(C)N(C(C=O)C(=O)O)[Si](C)(C)C1751.9Standard polar33892256
3-Oxoalanine,3TMS,isomer #1C[Si](C)(C)NC(=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C1497.8Semi standard non polar33892256
3-Oxoalanine,3TMS,isomer #1C[Si](C)(C)NC(=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C1401.4Standard non polar33892256
3-Oxoalanine,3TMS,isomer #1C[Si](C)(C)NC(=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C1675.2Standard polar33892256
3-Oxoalanine,3TMS,isomer #2C[Si](C)(C)OC(=O)C(C=O)N([Si](C)(C)C)[Si](C)(C)C1453.4Semi standard non polar33892256
3-Oxoalanine,3TMS,isomer #2C[Si](C)(C)OC(=O)C(C=O)N([Si](C)(C)C)[Si](C)(C)C1337.0Standard non polar33892256
3-Oxoalanine,3TMS,isomer #2C[Si](C)(C)OC(=O)C(C=O)N([Si](C)(C)C)[Si](C)(C)C1446.8Standard polar33892256
3-Oxoalanine,3TMS,isomer #3C[Si](C)(C)OC=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1651.0Semi standard non polar33892256
3-Oxoalanine,3TMS,isomer #3C[Si](C)(C)OC=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1485.2Standard non polar33892256
3-Oxoalanine,3TMS,isomer #3C[Si](C)(C)OC=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1629.7Standard polar33892256
3-Oxoalanine,4TMS,isomer #1C[Si](C)(C)OC=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1576.3Semi standard non polar33892256
3-Oxoalanine,4TMS,isomer #1C[Si](C)(C)OC=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1516.6Standard non polar33892256
3-Oxoalanine,4TMS,isomer #1C[Si](C)(C)OC=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1539.8Standard polar33892256
3-Oxoalanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)C=O1345.2Semi standard non polar33892256
3-Oxoalanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(N)C(=O)O1544.9Semi standard non polar33892256
3-Oxoalanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C=O)C(=O)O1465.1Semi standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(N)C(=O)O[Si](C)(C)C(C)(C)C1784.9Semi standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(N)C(=O)O[Si](C)(C)C(C)(C)C1683.5Standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(N)C(=O)O[Si](C)(C)C(C)(C)C2184.6Standard polar33892256
3-Oxoalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C=O)C(=O)O[Si](C)(C)C(C)(C)C1708.7Semi standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C=O)C(=O)O[Si](C)(C)C(C)(C)C1654.7Standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C=O)C(=O)O[Si](C)(C)C(C)(C)C1741.4Standard polar33892256
3-Oxoalanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=CO[Si](C)(C)C(C)(C)C)C(=O)O1962.5Semi standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=CO[Si](C)(C)C(C)(C)C)C(=O)O1765.0Standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=CO[Si](C)(C)C(C)(C)C)C(=O)O1989.5Standard polar33892256
3-Oxoalanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C(C=O)C(=O)O)[Si](C)(C)C(C)(C)C1850.9Semi standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C(C=O)C(=O)O)[Si](C)(C)C(C)(C)C1720.5Standard non polar33892256
3-Oxoalanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C(C=O)C(=O)O)[Si](C)(C)C(C)(C)C1879.8Standard polar33892256
3-Oxoalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2114.7Semi standard non polar33892256
3-Oxoalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1952.1Standard non polar33892256
3-Oxoalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2003.3Standard polar33892256
3-Oxoalanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2078.9Semi standard non polar33892256
3-Oxoalanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1990.3Standard non polar33892256
3-Oxoalanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1830.0Standard polar33892256
3-Oxoalanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2252.1Semi standard non polar33892256
3-Oxoalanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2043.8Standard non polar33892256
3-Oxoalanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1974.2Standard polar33892256
3-Oxoalanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2399.2Semi standard non polar33892256
3-Oxoalanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2207.5Standard non polar33892256
3-Oxoalanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1999.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-3badf1624e8be976ff3e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoalanine GC-MS (1 TMS) - 70eV, Positivesplash10-0229-9700000000-0a6f6ff14f13aa8906a12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoalanine 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 - 3-Oxoalanine 10V, Positive-QTOFsplash10-0k9i-9300000000-8deb05cddc33b63038e42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 20V, Positive-QTOFsplash10-0a4i-9000000000-66dca4d068e28977f3c72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 40V, Positive-QTOFsplash10-054o-9000000000-55c95a149f0b963695572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 10V, Negative-QTOFsplash10-0udi-5900000000-478630a15f5c327fcdfa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 20V, Negative-QTOFsplash10-0zgi-9500000000-3066713964a5e0f8569a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 40V, Negative-QTOFsplash10-0ab9-9000000000-4fa9f13f0177850fdeaf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 10V, Positive-QTOFsplash10-0a4i-9000000000-0f1ef0a1d167d92916de2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 20V, Positive-QTOFsplash10-0a4i-9000000000-efef21144041e76984b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 40V, Positive-QTOFsplash10-052f-9000000000-ab4bce6c79934227a9ed2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 10V, Negative-QTOFsplash10-0udi-2900000000-d042ac1f21f58860f67a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 20V, Negative-QTOFsplash10-05fr-9200000000-32cd289f148736c9e7482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoalanine 40V, Negative-QTOFsplash10-052f-9000000000-c1f539d1d861381411fc2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028313
KNApSAcK IDNot Available
Chemspider ID28
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound29
PDB IDNot Available
ChEBI ID17740
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. Lukatela G, Krauss N, Theis K, Selmer T, Gieselmann V, von Figura K, Saenger W: Crystal structure of human arylsulfatase A: the aldehyde function and the metal ion at the active site suggest a novel mechanism for sulfate ester hydrolysis. Biochemistry. 1998 Mar 17;37(11):3654-64. [PubMed:9521684 ]