You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:26:31 UTC
Update Date2019-07-23 06:16:23 UTC
HMDB IDHMDB0034566
Secondary Accession Numbers
  • HMDB34566
Metabolite Identification
Common NameNeotame
DescriptionPotential high-intensity sweetener, sweetness variously stated to be 40 x sucrose and 7000-13000 x sucrose Neotame is an artificial sweetener made by NutraSweet that is between 7,000 and 13,000 times sweeter than sucrose (table sugar). In the European Union it is known by the E number E961. Neotame is moderately heat stable and extremely potent. Neotame is rapidly metabolized, completely eliminated, and does not accumulate in the body
Structure
Data?1563862582
Synonyms
ValueSource
3-[(3,3-Dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)-C-hydroxycarbonimidoyl]propanoateGenerator
Chemical FormulaC20H30N2O5
Average Molecular Weight378.4626
Monoisotopic Molecular Weight378.21547208
IUPAC Name3-[(3,3-dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid
Traditional Name3-[(3,3-dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid
CAS Registry Number165450-17-9
SMILES
COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(O)=O)NCCC(C)(C)C
InChI Identifier
InChI=1S/C20H30N2O5/c1-20(2,3)10-11-21-15(13-17(23)24)18(25)22-16(19(26)27-4)12-14-8-6-5-7-9-14/h5-9,15-16,21H,10-13H2,1-4H3,(H,22,25)(H,23,24)
InChI KeyHLIAVLHNDJUHFG-UHFFFAOYSA-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
  • Aspartic acid or derivatives
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Methyl ester
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid ester
  • Carboxamide group
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid
  • Amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point80 - 83 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP0.42ALOGPS
logP-0.083ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)9.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.73 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.89 m³·mol⁻¹ChemAxon
Polarizability40.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5923000000-32b316dcb7691f6fc7a0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9082100000-44e7ca6efcad5c7c1c78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2209000000-d19a9a5790a672e592bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-6913000000-200e92bd1750b1e260f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009l-9500000000-25d473f3f05cab7dedf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-8a5a71caeab8b3ff01b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-1629000000-62264add783f4a6a781eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fte-3910000000-0c94d574c878a0faf288Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB013079
KNApSAcK IDNot Available
Chemspider ID3032042
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeotame
METLIN IDNot Available
PubChem Compound3804937
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .