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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-03-08 13:09:08 UTC
Update Date2022-03-07 02:49:11 UTC
HMDB IDHMDB0001894
Secondary Accession Numbers
  • HMDB01894
Metabolite Identification
Common NameAspartame
DescriptionAspartame is the name for an artificial, non-carbohydrate sweetener, aspartyl-phenylalanine-1-methyl ester; i.e., the methyl ester of the dipeptide of the amino acids aspartic acid and phenylalanine. It is marketed under a number of trademark names, such as Equal, and Canderel, and is an ingredient of approximately 6,000 consumer foods and beverages sold worldwide. It is commonly used in diet soft drinks, and is often provided as a table condiment. It is also used in some brands of chewable vitamin supplements. In the European Union, it is also known under the E number (additive code) E951. Aspartame is also one of the sugar substitutes used by diabetics. Upon ingestion, aspartame breaks down into several constituent chemicals, including the naturally-occurring essential amino acid phenylalanine which is a health hazard to the few people born with phenylketonuria, a congenital inability to process phenylalanine. Aspartic acid is an amino acid commonly found in foods. Approximately 40% of aspartame (by mass) is broken down into aspartic acid. Because aspartame is metabolized and absorbed very quickly (unlike aspartic acid-containing proteins in foods), it is known that aspartame could spike blood plasma levels of aspartate. Aspartic acid is in a class of chemicals known as excitotoxins. Abnormally high levels of excitotoxins have been shown in hundreds of animals studies to cause damage to areas of the brain unprotected by the blood-brain barrier and a variety of chronic diseases arising out of this neurotoxicity.
Structure
Data?1582752215
Synonyms
ValueSource
1-Methyl N-L-alpha-aspartyl-L-phenylalanateChEBI
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl esterChEBI
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acidChEBI
AminoSweetChEBI
Asp-phe-omeChEBI
AspartamChEBI
AspartamoChEBI
AspartamumChEBI
Aspartylphenylalanine methyl esterChEBI
e 951ChEBI
L-Aspartyl-L-phenylalanine methyl esterChEBI
NutraSweetChEBI
SanectaChEBI
1-Methyl N-L-a-aspartyl-L-phenylalanateGenerator
1-Methyl N-L-a-aspartyl-L-phenylalanic acidGenerator
1-Methyl N-L-alpha-aspartyl-L-phenylalanic acidGenerator
1-Methyl N-L-α-aspartyl-L-phenylalanateGenerator
1-Methyl N-L-α-aspartyl-L-phenylalanic acidGenerator
3-Amino-N-(a-carboxyphenethyl)succinamate N-methyl esterGenerator
3-Amino-N-(a-carboxyphenethyl)succinamic acid N-methyl esterGenerator
3-Amino-N-(alpha-carboxyphenethyl)succinamate N-methyl esterGenerator
3-Amino-N-(α-carboxyphenethyl)succinamate N-methyl esterGenerator
3-Amino-N-(α-carboxyphenethyl)succinamic acid N-methyl esterGenerator
3-Amino-N-(a-methoxycarbonylphenethyl) succinamateGenerator
3-Amino-N-(a-methoxycarbonylphenethyl) succinamic acidGenerator
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamateGenerator
3-Amino-N-(α-methoxycarbonylphenethyl) succinamateGenerator
3-Amino-N-(α-methoxycarbonylphenethyl) succinamic acidGenerator
CanderelHMDB
Dipeptide sweetenerHMDB
L-Aspartyl-L-3-phenylalanine methyl esterHMDB
L-Aspartyl-L-phenylalanyl methyl esterHMDB
Methyl aspartylphenylalanateHMDB
Pal sweetHMDB
Palsweet dietHMDB
Sweet dipeptideHMDB
Methyl aspartylphenylalanineHMDB
Methyl ester, aspartylphenylalanineHMDB
Muro brand OF aspartameHMDB
Aspartame hermes brandHMDB
Aspartame prodes brandHMDB
Aspartylphenylalanine, methylHMDB
GoldswiteHMDB
Hermesetas goldHMDB
Aspartame fuca brandHMDB
Aspartame muro brandHMDB
Diététiques et santé brand OF aspartameHMDB
Fuca brand OF aspartameHMDB
Prodes brand OF aspartameHMDB
Tri sweetHMDB
Gold, hermesetasHMDB
Hermes brand OF aspartameHMDB
MilisucreHMDB
NozucarHMDB
Tri-sweetHMDB
TriSweetHMDB
Chemical FormulaC14H18N2O5
Average Molecular Weight294.3031
Monoisotopic Molecular Weight294.121571696
IUPAC Name(3S)-3-amino-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
Traditional Nameaspartame
CAS Registry Number22839-47-0
SMILES
COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O
InChI Identifier
InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1
InChI KeyIAOZJIPTCAWIRG-QWRGUYRKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Phenylalanine or derivatives
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid ester
  • Organic 1,3-dipolar compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point246.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg166.71330932474
[M+H]+MetCCS_train_pos169.63630932474
[M-H]-Not Available166.713http://allccs.zhulab.cn/database/detail?ID=AllCCS00000047
[M+H]+Not Available169.982http://allccs.zhulab.cn/database/detail?ID=AllCCS00000047
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.65 g/LALOGPS
logP-1.2ALOGPS
logP-2.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)8.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.22 m³·mol⁻¹ChemAxon
Polarizability29.56 ųChemAxon
Number of Rings1ChemAxon
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]+171.82231661259
DarkChem[M-H]-165.33331661259
AllCCS[M+H]+168.59132859911
AllCCS[M-H]-167.83632859911
DeepCCS[M+H]+177.54630932474
DeepCCS[M-H]-175.18730932474
DeepCCS[M-2H]-209.02330932474
DeepCCS[M+Na]+184.2530932474
AllCCS[M+H]+168.632859911
AllCCS[M+H-H2O]+165.532859911
AllCCS[M+NH4]+171.532859911
AllCCS[M+Na]+172.332859911
AllCCS[M-H]-167.832859911
AllCCS[M+Na-2H]-168.132859911
AllCCS[M+HCOO]-168.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AspartameCOC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O3964.0Standard polar33892256
AspartameCOC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O2099.6Standard non polar33892256
AspartameCOC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O2483.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aspartame,1TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(=O)O[Si](C)(C)C2367.6Semi standard non polar33892256
Aspartame,1TMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N[Si](C)(C)C2399.7Semi standard non polar33892256
Aspartame,1TMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC(=O)O)[Si](C)(C)C2369.4Semi standard non polar33892256
Aspartame,2TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C)N[Si](C)(C)C2408.4Semi standard non polar33892256
Aspartame,2TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C)N[Si](C)(C)C2426.9Standard non polar33892256
Aspartame,2TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C)N[Si](C)(C)C3352.8Standard polar33892256
Aspartame,2TMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC(=O)O[Si](C)(C)C)[Si](C)(C)C2349.3Semi standard non polar33892256
Aspartame,2TMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC(=O)O[Si](C)(C)C)[Si](C)(C)C2398.6Standard non polar33892256
Aspartame,2TMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC(=O)O[Si](C)(C)C)[Si](C)(C)C3582.2Standard polar33892256
Aspartame,2TMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N[Si](C)(C)C)[Si](C)(C)C2407.4Semi standard non polar33892256
Aspartame,2TMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N[Si](C)(C)C)[Si](C)(C)C2440.4Standard non polar33892256
Aspartame,2TMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N[Si](C)(C)C)[Si](C)(C)C3327.9Standard polar33892256
Aspartame,2TMS,isomer #4COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N([Si](C)(C)C)[Si](C)(C)C2525.7Semi standard non polar33892256
Aspartame,2TMS,isomer #4COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N([Si](C)(C)C)[Si](C)(C)C2496.4Standard non polar33892256
Aspartame,2TMS,isomer #4COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N([Si](C)(C)C)[Si](C)(C)C3426.6Standard polar33892256
Aspartame,3TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C2404.9Semi standard non polar33892256
Aspartame,3TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C2476.5Standard non polar33892256
Aspartame,3TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C3053.8Standard polar33892256
Aspartame,3TMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2511.9Semi standard non polar33892256
Aspartame,3TMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2543.9Standard non polar33892256
Aspartame,3TMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3135.9Standard polar33892256
Aspartame,3TMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2522.0Semi standard non polar33892256
Aspartame,3TMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2559.3Standard non polar33892256
Aspartame,3TMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C3134.0Standard polar33892256
Aspartame,4TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2559.2Semi standard non polar33892256
Aspartame,4TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2596.1Standard non polar33892256
Aspartame,4TMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2922.5Standard polar33892256
Aspartame,1TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(=O)O[Si](C)(C)C(C)(C)C2602.3Semi standard non polar33892256
Aspartame,1TBDMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N[Si](C)(C)C(C)(C)C2599.7Semi standard non polar33892256
Aspartame,1TBDMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC(=O)O)[Si](C)(C)C(C)(C)C2604.9Semi standard non polar33892256
Aspartame,2TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2829.7Semi standard non polar33892256
Aspartame,2TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2797.5Standard non polar33892256
Aspartame,2TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3447.6Standard polar33892256
Aspartame,2TBDMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2841.4Semi standard non polar33892256
Aspartame,2TBDMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2799.1Standard non polar33892256
Aspartame,2TBDMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N)CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3633.5Standard polar33892256
Aspartame,2TBDMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2860.6Semi standard non polar33892256
Aspartame,2TBDMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2787.6Standard non polar33892256
Aspartame,2TBDMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3426.5Standard polar33892256
Aspartame,2TBDMS,isomer #4COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2983.3Semi standard non polar33892256
Aspartame,2TBDMS,isomer #4COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2834.7Standard non polar33892256
Aspartame,2TBDMS,isomer #4COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3461.8Standard polar33892256
Aspartame,3TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3060.9Semi standard non polar33892256
Aspartame,3TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3007.3Standard non polar33892256
Aspartame,3TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3317.1Standard polar33892256
Aspartame,3TBDMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3211.9Semi standard non polar33892256
Aspartame,3TBDMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3063.2Standard non polar33892256
Aspartame,3TBDMS,isomer #2COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3332.3Standard polar33892256
Aspartame,3TBDMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3215.2Semi standard non polar33892256
Aspartame,3TBDMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3060.7Standard non polar33892256
Aspartame,3TBDMS,isomer #3COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3332.5Standard polar33892256
Aspartame,4TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3428.2Semi standard non polar33892256
Aspartame,4TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3268.1Standard non polar33892256
Aspartame,4TBDMS,isomer #1COC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3237.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aspartame GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9220000000-2625126bd17025b839332017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aspartame GC-MS (1 TMS) - 70eV, Positivesplash10-03di-5904000000-075be5fd36b94f4256502017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aspartame GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00ns-0690000000-e92f66ca1ae82b0ccd812012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-2900000000-8eec324eec1e64466b1c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-01b9-2900000000-e8415697953bc139924b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame LC-ESI-qTof , Positive-QTOFsplash10-0080-0890000000-b2e2c2a89ceaf3d1f9db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame LC-ESI-QTOF , positive-QTOFsplash10-00e9-0930000000-d8dbb5a34c019dc707082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame , positive-QTOFsplash10-0080-0890000000-b2e2c2a89ceaf3d1f9db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 40V, Negative-QTOFsplash10-0007-9300000000-752aa89264f270a0fa052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 20V, Negative-QTOFsplash10-0uka-6970000000-013c7cbdca3d99b6f9fd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame -1V, Positive-QTOFsplash10-00e9-0930000000-d8dbb5a34c019dc707082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 40V, Positive-QTOFsplash10-00di-4900000000-44d957a1f7597badb9882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 10V, Negative-QTOFsplash10-0j4i-0290000000-13341a263598276b72502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 10V, Positive-QTOFsplash10-001r-0590000000-892944c774f24420614a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 20V, Positive-QTOFsplash10-00di-1910000000-d608ab28a66f1df0e8ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 20V, Negative-QTOFsplash10-0fdn-7960000000-f6a714d56477fcabf6fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 30V, Negative-QTOFsplash10-00r7-9510000000-4252f225428cba6bb01b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 10V, Negative-QTOFsplash10-0j4i-0290000000-08042f6313a2bfffda832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aspartame 40V, Negative-QTOFsplash10-00kg-9400000000-a62cb6f22dc5c7b0f1d42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aspartame 10V, Positive-QTOFsplash10-004j-4390000000-5ea0d55c8c75f40eefde2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aspartame 20V, Positive-QTOFsplash10-0109-9730000000-badb4105789050b523462017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aspartame 40V, Positive-QTOFsplash10-0006-9100000000-22c71b3445a360c7886a2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aspartame 10V, Negative-QTOFsplash10-0006-0290000000-c48af459412db76084cc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aspartame 20V, Negative-QTOFsplash10-02bg-1690000000-df82228a7343c200b8d42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aspartame 40V, Negative-QTOFsplash10-03gu-9700000000-db183663829759af70f92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aspartame 10V, Negative-QTOFsplash10-0006-0090000000-c13994947a4a009ec6b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aspartame 20V, Negative-QTOFsplash10-004j-3960000000-685d025546bdd8eba5c02021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue Locations
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00168
Phenol Explorer Compound IDNot Available
FooDB IDFDB000569
KNApSAcK IDNot Available
Chemspider ID118630
KEGG Compound IDC11045
BioCyc IDCPD-5583
BiGG IDNot Available
Wikipedia LinkAspartame
METLIN ID6377
PubChem Compound134601
PDB IDNot Available
ChEBI ID2877
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFuganti, Claudio; Grasselli, Piero; Malpezzi, Luciana; Casati, Paolo. Synthesis of aspartame via asymmetric hydrogenation of N-protected (Z)-N-a-L-aspartyl-D-phenylalanine methyl ester. Journal of Organic Chemistry (1986), 51(7), 1126-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lam S: Stereoselective analysis of D and L dansyl amino acids as the mixed chelate copper(II) complexes by HPLC. J Chromatogr Sci. 1984 Sep;22(9):416-23. [PubMed:6490790 ]
  2. Lam S, Azumaya H, Karmen A: High-performance liquid chromatography of amino acids in urine and cerebrospinal fluid. J Chromatogr. 1984 Oct 19;302:21-9. [PubMed:6501504 ]
  3. Fernstrom JD: Dietary amino acids and brain function. J Am Diet Assoc. 1994 Jan;94(1):71-7. [PubMed:7903674 ]
  4. Azcurra AI, Calamari SE, Yankilevich ER, Battellino LJ, Cattoni ST, Colantonio G: [Effects of local treatment with sodium fluoride mouthrinse on peroxidase and hypothiocyanite saliva levels in adolescent]/. Acta Physiol Pharmacol Ther Latinoam. 1997;47(4):211-20. [PubMed:9504181 ]
  5. Busch U, Schmid J, Heinzel G, Schmaus H, Baierl J, Huber C, Roth W: Pharmacokinetics of meloxicam in animals and the relevance to humans. Drug Metab Dispos. 1998 Jun;26(6):576-84. [PubMed:9616195 ]
  6. Bidiwala KS, Lorenz JM, Kleinman LI: Renal function correlates of postnatal diuresis in preterm infants. Pediatrics. 1988 Jul;82(1):50-8. [PubMed:3288958 ]
  7. Burns TS, Stargel WW, Tschanz C, Kotsonis FN, Hurwitz A: Aspartame and sucrose produce a similar increase in the plasma phenylalanine to large neutral amino acid ratio in healthy subjects. Pharmacology. 1991;43(4):210-9. [PubMed:1771173 ]
  8. Romano M, Casacci F, De Marchi F, Pacei T, Esteve A, Lomuscio G, Mennini T, Salmona M: Effects of aspartame and carbohydrate administration on human and rat plasma large neutral amino acid levels and rat brain amino acid and monoamine levels. J Nutr. 1989 Jan;119(1):75-81. [PubMed:2913236 ]
  9. McMasters DR, Vedani A: Ochratoxin binding to phenylalanyl-tRNA synthetase: computational approach to the mechanism of ochratoxicosis and its antagonism. J Med Chem. 1999 Aug 12;42(16):3075-86. [PubMed:10447951 ]
  10. Kochansky CJ, Rippley RK, Yan KX, Song H, Wallace MA, Dean D, Jones AN, Lasseter K, Schwartz J, Vincent SH, Franklin RB, Wagner J: Absorption, metabolism, and excretion of [14C]MK-0767 (2-methoxy-5-(2,4-dioxo-5-thiazolidinyl)-N-[[4-(trifluoromethyl)phenyl] methyl]benzamide) in humans. Drug Metab Dispos. 2006 Sep;34(9):1457-61. Epub 2006 Jun 13. [PubMed:16772365 ]
  11. Koeppe RA, Shulkin BL, Rosenspire KC, Shaw LA, Betz AL, Mangner T, Price JC, Agranoff BW: Effect of aspartame-derived phenylalanine on neutral amino acid uptake in human brain: a positron emission tomography study. J Neurochem. 1991 May;56(5):1526-35. [PubMed:2013754 ]
  12. Yang D, Beylot M, Agarwal KC, Soloviev MV, Brunengraber H: Assay of the human liver citric acid cycle probe phenylacetylglutamine and of phenylacetate in plasma by gas chromatography-mass spectrometry. Anal Biochem. 1993 Jul;212(1):277-82. [PubMed:8368503 ]
  13. Maher TJ, Wurtman RJ: Possible neurologic effects of aspartame, a widely used food additive. Environ Health Perspect. 1987 Nov;75:53-7. [PubMed:3319565 ]
  14. Wurtman RJ, Maher TJ: Effects of oral aspartame on plasma phenylalanine in humans and experimental rodents. Short note. J Neural Transm. 1987;70(1-2):169-73. [PubMed:3668518 ]

Enzymes

General function:
Involved in ion channel activity
Specific function:
Receptor-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. May be involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL
Gene Name:
TRPV1
Uniprot ID:
Q8NER1
Molecular weight:
94955.3
References
  1. Riera CE, Vogel H, Simon SA, le Coutre J: Artificial sweeteners and salts producing a metallic taste sensation activate TRPV1 receptors. Am J Physiol Regul Integr Comp Physiol. 2007 Aug;293(2):R626-34. Epub 2007 Jun 13. [PubMed:17567713 ]
General function:
Involved in G-protein coupled receptor activity
Specific function:
Putative taste receptor. TAS1R1/TAS1R3 responds to the umami taste stimulus (the taste of monosodium glutamate). TAS1R2/TAS1R3 recognizes diverse natural and synthetic sweeteners. TAS1R3 is essential for the recognition and response to the disaccharide trehalose. Sequence differences within and between species can significantly influence the selectivity and specificity of taste responses
Gene Name:
TAS1R3
Uniprot ID:
Q7RTX0
Molecular weight:
93385.2
General function:
Involved in G-protein coupled receptor activity
Specific function:
Putative taste receptor. TAS1R2/TAS1R3 recognizes diverse natural and synthetic sweeteners
Gene Name:
TAS1R2
Uniprot ID:
Q8TE23
Molecular weight:
95182.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Xu H, Staszewski L, Tang H, Adler E, Zoller M, Li X: Different functional roles of T1R subunits in the heteromeric taste receptors. Proc Natl Acad Sci U S A. 2004 Sep 28;101(39):14258-63. Epub 2004 Sep 7. [PubMed:15353592 ]
  4. Cui M, Jiang P, Maillet E, Max M, Margolskee RF, Osman R: The heterodimeric sweet taste receptor has multiple potential ligand binding sites. Curr Pharm Des. 2006;12(35):4591-600. [PubMed:17168764 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular weight:
59970.9
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456 ]
  2. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. [PubMed:10336520 ]