CHEBI:49432 - 5-hydroxyectoine

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ChEBI Name 5-hydroxyectoine
ChEBI ID CHEBI:49432
Definition A carboxamidine heterocycle which is obtained by formal condensation of 4-amino-L-allothreonine with acetic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C6H10N2O3
Net Charge 0
Average Mass 158.15520
Monoisotopic Mass 158.06914
InChI InChI=1S/C6H10N2O3/c1-3-7-2-4(9)5(8-3)6(10)11/h4-5,9H,2H2,1H3,(H,7,8)(H,10,11)/t4-,5-/m0/s1
InChIKey KIIBBJKLKFTNQO-WHFBIAKZSA-N
SMILES CC1=N[C@@H]([C@@H](O)CN1)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 )
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ChEBI Ontology
Outgoing 5-hydroxyectoine (CHEBI:49432) is a 1,4,5,6-tetrahydropyrimidines (CHEBI:78715)
5-hydroxyectoine (CHEBI:49432) is a carboxamidine (CHEBI:35359)
5-hydroxyectoine (CHEBI:49432) is a monocarboxylic acid (CHEBI:25384)
5-hydroxyectoine (CHEBI:49432) is a secondary alcohol (CHEBI:35681)
5-hydroxyectoine (CHEBI:49432) is conjugate acid of 5-hydroxyectoinate (CHEBI:63524)
5-hydroxyectoine (CHEBI:49432) is tautomer of 5-hydroxyectoine zwitterion (CHEBI:85413)
Incoming 5-hydroxyectoinate (CHEBI:63524) is conjugate base of 5-hydroxyectoine (CHEBI:49432)
5-hydroxyectoine zwitterion (CHEBI:85413) is tautomer of 5-hydroxyectoine (CHEBI:49432)
IUPAC Name
(4S,5S)-5-hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Synonyms Sources
(4S,5S)-2-methyl-4-carboxy-5-hydroxy-3,4,5,6-tetrahydropyrimidine ChEBI
(4S,5S)-5-HYDROXY-2-METHYL-1,4,5,6-TETRAHYDROPYRIMIDINE-4-CARBOXYLIC ACID PDBeChem
(S,S)-2-methyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid ChEBI
4-pyrimidinecarboxylic acid, 1,4,5,6-tetrahydro-5-hydroxy-2-methyl-, (4S,5S)- ChEBI
β-hydroxyectoine ChEBI
hydroxyectoine ChEBI
Manual Xrefs Databases
6CS PDBeChem
C16432 KEGG COMPOUND
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Registry Number Type Source
14124667 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16098972 PubMed citation Europe PMC
Last Modified
06 June 2014
General Comment
2010-12-21 5-Hydroxyectoine is one 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.