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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:31 -0600
Update Date	2015-06-03 17:21:16 -0600
Secondary Accession Numbers	ECMDB21379
Identification
Name:	Ectoine
Description	Ectoine (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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaac04978> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Alpha amino acids and derivatives
Alternative Parents	Hydropyrimidine carboxylic acids and derivatives Imidolactams Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Carboxylic acids Carboximidamides Carboxamidines Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 10.3 g/L ALOGPS logP -0.23 ALOGPS logP -2.5 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 2.87 ChemAxon pKa (Strongest Basic) 10.52 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 61.69 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 35.04 m³·mol⁻¹ ChemAxon Polarizability 14.04 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-002f-3900000000-2b8711d6a2ef6e5dec04 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-9500000000-f33d65da7d2f7603e061 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0zfu-9000000000-1f988a0dc3dd0a827997 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0006-2900000000-9621d62c2f61b55e5bf6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0007-9600000000-1e319dd9883aac16eab2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0f6x-9000000000-7841100c6c78e84e0b4e View in MoNA
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 27592 HMDB ID Not Available Pubchem Compound ID 126041 Kegg ID C06231 ChemSpider ID 670 Wikipedia Ectoine BioCyc ID ECTOINE EcoCyc ID ECTOINE

Transporters