CHEBI:27592 - ectoine

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ChEBI Name ectoine
ChEBI ID CHEBI:27592
Definition A carboxamidine heterocycle obtained by formal condensation of (2S)-2,4-diaminobutanoic acid with acetic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4756, CHEBI:23898, CHEBI:49406
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Formula C6H10N2O2
Net Charge 0
Average Mass 142.15588
Monoisotopic Mass 142.074
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)/t5-/m0/s1
InChIKey WQXNXVUDBPYKBA-YFKPBYRVSA-N
SMILES CC1=N[C@@H](CCN1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): osmolyte
A solute used by a cell under water stress to maintain cell volume.
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ChEBI Ontology
Outgoing ectoine (CHEBI:27592) has role osmolyte (CHEBI:25728)
ectoine (CHEBI:27592) is a 1,4,5,6-tetrahydropyrimidines (CHEBI:78715)
ectoine (CHEBI:27592) is a carboxamidine (CHEBI:35359)
ectoine (CHEBI:27592) is a monocarboxylic acid (CHEBI:25384)
ectoine (CHEBI:27592) is conjugate acid of ectoinate (CHEBI:63475)
ectoine (CHEBI:27592) is tautomer of ectoine zwitterion (CHEBI:58515)
Incoming ectoinate (CHEBI:63475) is conjugate base of ectoine (CHEBI:27592)
ectoine zwitterion (CHEBI:58515) is tautomer of ectoine (CHEBI:27592)
IUPAC Name
(4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Synonyms Sources
(+)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid ChemIDplus
Ectoine KEGG COMPOUND
L-Ectoine KEGG COMPOUND
L-ectoine ChEBI
Database Links Databases
4CS PDBeChem
C06231 KEGG COMPOUND
Ectoine Wikipedia
ECTOINE MetaCyc
View more database links
Registry Numbers Types Sources
7288977 Reaxys Registry Number Reaxys
7288977 Beilstein Registry Number Beilstein
96702-03-3 CAS Registry Number ChemIDplus
Last Modified
28 July 2014
General Comment
2010-12-21 Ectoine is one of the most widely occurring of the 'compatible solute' organic osmolytes, used by many microorganisms to actively counteract the detrimental effects of water efflux across the semi-permeable cytoplasmic membrane on cell physiology. These compounds are fully congruous with metabolism and other cellular functions and so can be amassed to very high intracellular levels. A direct consequence of compatible solute accumulation is the raising of the osmotic potential of the cytoplasm, so allowing retention of water by the microbial cell and promoting water reentry.