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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2019-05-29 15:12:59 UTC
Update Date2019-09-18 18:25:40 UTC
HMDB IDHMDB0240365
Secondary Accession NumbersNone
Metabolite Identification
Common NameN,​N,​N-​Trimethyl-​L-​alanyl-​L-​proline betaine
DescriptionN,N,N-Trimethyl-L-alanyl-L-proline betaine (TMAP) belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. TMAP was previously an unknown potential plasma biomarker for glomerular filtration rate (GFR) but its structure has since been elucidated (PMID: 28706470 ). TMAP has also been identified as a potential plasma biomarker of reduced kidney function in early chronic kidney disease (CKD), end stage renal disease (ESRD), and hemodialytic clearance (PMID: 31048706 ).
Structure
Data?1568831140
Synonyms
ValueSource
N,N,N-Trimethyl-L-alanyl-L-proline betaineHMDB
N,N,N-Trimethylalanylproline betaineHMDB
TMAPHMDB
L,L-TMAPHMDB
Chemical FormulaC11H20N2O3
Average Molecular Weight228.292
Monoisotopic Molecular Weight228.147392512
IUPAC Name(2S)-1-[(2S)-2-(trimethylazaniumyl)propanoyl]pyrrolidine-2-carboxylate
Traditional Name(2S)-1-[(2S)-2-(trimethylammonio)propanoyl]pyrrolidine-2-carboxylate
CAS Registry Number2177265-93-7
SMILES
C[C@@H](C(=O)N1CCC[C@H]1C([O-])=O)[N+](C)(C)C
InChI Identifier
InChI=1S/C11H20N2O3/c1-8(13(2,3)4)10(14)12-7-5-6-9(12)11(15)16/h8-9H,5-7H2,1-4H3/t8-,9-/m0/s1
InChI KeyKXONJPJIFNGMCN-IUCAKERBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Proline or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-acylpyrrolidine
  • Tetraalkylammonium salt
  • Tertiary carboxylic acid amide
  • Quaternary ammonium salt
  • Pyrrolidine
  • Carboxylic acid salt
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-4.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.85ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.3 m³·mol⁻¹ChemAxon
Polarizability24.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound134218393
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. Velenosi TJ, Thomson BKA, Tonial NC, RaoPeters AAE, Mio MA, Lajoie GA, Garg AX, House AA, Urquhart BL: Untargeted metabolomics reveals N, N, N-trimethyl-L-alanyl-L-proline betaine (TMAP) as a novel biomarker of kidney function. Sci Rep. 2019 May 2;9(1):6831. doi: 10.1038/s41598-019-42992-3. [PubMed:31048706 ]
  2. Zhang Q, Ford LA, Evans AM, Toal DR: Structure elucidation of metabolite x17299 by interpretation of mass spectrometric data. Metabolomics. 2017;13(8):92. doi: 10.1007/s11306-017-1231-x. Epub 2017 Jun 24. [PubMed:28706470 ]