Record Information
Version2.0
Creation Date2012-07-30 14:55:31 -0600
Update Date2015-06-03 17:21:16 -0600
Secondary Accession Numbers
  • ECMDB21379
Identification
Name:Ectoine
DescriptionEctoine (1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a compatible solute which serves as a protective substance by acting as an osmolyte and thus helps organisms survive extreme osmotic stress. Ectoine is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism Ectothiorhodospira halochloris, but has since been found in a wide range of gram-negative and gram-positive bacteria. Some other species ectoine was found in:
Structure
Thumb
Synonyms:
  • (+)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylate
  • (+)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid
  • (4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylate
  • (4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
  • 1,4,5,6-Tetrahydro-2-methyl-4-pyrimidine carboxylate
  • 1,4,5,6-Tetrahydro-2-methyl-4-pyrimidine carboxylic acid
  • Ectoine
  • L-Ectoine
Chemical Formula:C6H10N2O2
Weight:Average: 142.1558
Monoisotopic: 142.074227574
InChI Key:WQXNXVUDBPYKBA-UHFFFAOYSA-N
InChI:InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)
CAS number:Not Available
IUPAC Name:2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Traditional IUPAC Name:ectoine
SMILES:CC1=NCCC(N1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • 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
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility10.3 g/LALOGPS
logP-0.23ALOGPS
logP-2.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.04 m³·mol⁻¹ChemAxon
Polarizability14.04 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-3900000000-2b8711d6a2ef6e5dec04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9500000000-f33d65da7d2f7603e061View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-9000000000-1f988a0dc3dd0a827997View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-9621d62c2f61b55e5bf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-9600000000-1e319dd9883aac16eab2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9000000000-7841100c6c78e84e0b4eView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27592
HMDB IDNot Available
Pubchem Compound ID126041
Kegg IDC06231
ChemSpider ID670
WikipediaEctoine
BioCyc IDECTOINE
EcoCyc IDECTOINE

Transporters

General function:
Involved in transporter activity
Specific function:
Proton symporter that senses osmotic shifts and responds by importing osmolytes such as proline, glycine betaine, stachydrine, pipecolic acid, ectoine and taurine. It is both an osmosensor and an osmoregulator which is available to participate early in the bacterial osmoregulatory response
Gene Name:
proP
Uniprot ID:
P0C0L7
Molecular weight:
54845