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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2020-06-03 16:21:17 UTC
Update Date2020-06-04 20:23:51 UTC
HMDB IDHMDB0240650
Secondary Accession NumbersNone
Metabolite Identification
Common NameEctoine
DescriptionEctoine 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). Ectoine has been identified in urine (PMID: 22409530 ).
Structure
Data?1591302231
Synonyms
ValueSource
(+)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acidChEBI
L-EctoineChEBI
(4S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylateKegg
(+)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylateGenerator
(4S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acidGenerator
1,4,5,6-tetrahydro-2-Methyl-4-pyrimidinecarboxylic acidMeSH
EctoinMeSH
(4S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acidHMDB
(4S)-3,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acidHMDB
(S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acidHMDB
EctoineHMDB
Pyrostatin BHMDB
Pyrostatine BHMDB
Chemical FormulaC6H10N2O2
Average Molecular Weight142.1558
Monoisotopic Molecular Weight142.074227574
IUPAC Name(4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Traditional Nameectoine
CAS Registry Number96702-03-3
SMILES
CC1=NCC[C@H](N1)C(O)=O
InChI Identifier
InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1
InChI KeyWQXNXVUDBPYKBA-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Hydropyrimidine carboxylic acid derivative
  • Hydropyrimidine
  • 1,4,5,6-tetrahydropyrimidine
  • Imidolactam
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Role

Indirect biological role:

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-0.23ALOGPS
logP-2.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.75ChemAxon
pKa (Strongest Basic)10.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.04 m³·mol⁻¹ChemAxon
Polarizability14.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID112069
KEGG Compound IDC06231
BioCyc IDECTOINE
BiGG IDNot Available
Wikipedia LinkEctoine
METLIN IDNot Available
PubChem Compound126041
PDB IDNot Available
ChEBI ID27592
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang T, Creek DJ, Barrett MP, Blackburn G, Watson DG: Evaluation of coupling reversed phase, aqueous normal phase, and hydrophilic interaction liquid chromatography with Orbitrap mass spectrometry for metabolomic studies of human urine. Anal Chem. 2012 Feb 21;84(4):1994-2001. doi: 10.1021/ac2030738. Epub 2012 Feb 1. [PubMed:22409530 ]
  2. Mair RD, Sirich TL, Plummer NS, Meyer TW: Characteristics of Colon-Derived Uremic Solutes. Clin J Am Soc Nephrol. 2018 Sep 7;13(9):1398-1404. doi: 10.2215/CJN.03150318. Epub 2018 Aug 7. [PubMed:30087103 ]