NEOTAME (CHEM006869)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:18:42 UTC
Update Date2026-03-27 01:51:10 UTC
Accession NumberCHEM006869
Identification
Common NameNEOTAME
ClassSmall Molecule
DescriptionA dipeptide composed of N-(3,3-dimethylbutyl)-L-aspartic acid and methyl L-phenylalanate units joined by a peptide linkage.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-[N-(3,3-Dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine methyl esterChEBI
N-[N-(3,3-Dimethylbutyl)-L-a-aspartyl]-L-phenylalanine methyl esterGenerator
N-[N-(3,3-Dimethylbutyl)-L-α-aspartyl]-L-phenylalanine methyl esterGenerator
(3S)-3-(3,3-dimethylbutylamino)-4-[[(2S)-1-Methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoateGenerator
NeotameMeSH
N-(N-(3,3-Dimethylbutyl)-L-alpha-aspartyl)-L-phenylalanine 1-methyl esterMeSH
Chemical FormulaC20H30N2O5
Average Molecular Mass378.469 g/mol
Monoisotopic Mass378.215 g/mol
CAS Registry Number165450-17-9
IUPAC Name(3S)-3-[(3,3-dimethylbutyl)amino]-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-C-hydroxycarbonimidoyl}propanoic acid
Traditional Name(3S)-3-[(3,3-dimethylbutyl)amino]-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-C-hydroxycarbonimidoyl}propanoic acid
SMILES[H][C@@](CC(O)=O)(NCCC(C)(C)C)C(O)=N[C@@]([H])(CC1=CC=CC=C1)C(=O)OC
InChI IdentifierInChI=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)/t15-,16-/m0/s1
InChI KeyHLIAVLHNDJUHFG-HOTGVXAUSA-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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP1.02ALOGPS
logP0.51ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.22 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity101.41 m³·mol⁻¹ChemAxon
Polarizability40.48 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3609000000-0874e56db8c9c14fac21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00vr-4901000000-cd61eb24f785a2ceb9d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9500000000-188135365a364a77e896Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0129000000-2af28116c6e9332ff809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-1659000000-bcb75984d586337ebd94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v13-5900000000-62f2ba5c16a54047b9edSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNeotame
Chemspider IDNot Available
ChEBI ID83503
PubChem Compound ID9810996
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23595253
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24612793
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25216979