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 142.07423
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
Manual Xrefs Databases
4CS PDBeChem
C06231 KEGG COMPOUND
Ectoine Wikipedia
ECTOINE MetaCyc
View more database links
Registry Numbers Types Sources
7288977 Reaxys Registry Number Reaxys
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.