(2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol (CHEBI:44800)

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ChEBI Name	(2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol

ChEBI ID	CHEBI:44800

ChEBI ASCII Name	(2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol

Definition	A tetrahydroxytetrahydrofuran in which the hydroxy groups are located at positions 2, 3, 4, and 4 and which is substituted by a methyl group at position 2 (the 2R,4S diastereoisomer).

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C5H10O5

Net Charge

Average Mass

150.12990

Monoisotopic Mass

150.05282

InChI

InChI=1S/C5H10O5/c1-4(7)5(8,9)3(6)2-10-4/h3,6-9H,2H2,1H3/t3-,4+/m0/s1

InChIKey

BVIYGXUQVXBHQS-IUYQGCFVSA-N

SMILES

C[C@@]1(O)OC[C@H](O)C1(O)O

Roles Classification
Biological Role(s):	autoinducer A signalling molecule produced and used by bacteria participating in quorum sensing, that is, in cell-cell communication to coordinate community-wide regulation of processes such as biofilm formation, virulence, and bioluminescence in populations of bacteria. Such communication can occur both within and between different species of bacteria.

ChEBI Ontology
Outgoing	(2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol (CHEBI:44800) has role autoinducer (CHEBI:71338) (2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol (CHEBI:44800) is a cyclic ketal (CHEBI:59779) (2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol (CHEBI:44800) is a ketone hydrate (CHEBI:63734) (2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol (CHEBI:44800) is a tetrahydroxytetrahydrofuran (CHEBI:47041) (2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol (CHEBI:44800) is a tetrol (CHEBI:33573)

IUPAC Name

(2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol

Synonyms	Sources
(2R,4S)-2-METHYL-2,3,3,4-TETRAHYDROXYTETRAHYDROFURAN	PDBeChem
(2R,4S)-2-methyldihydrofuran-2,3,3,4(2H)-tetrol	IUPAC
(2R,4S)-2-methyloxolane-2,3,3,4-tetrol	ChEBI
(2R,4S)-2-methyltetrahydrofuran-2,3,3,4-tetrol	UniProt
(R)-THMF	MetaCyc
AI-2	MetaCyc
auto inducer 2	MetaCyc

Registry Number	Type	Source
9997002	Reaxys Registry Number	Reaxys

Citation	Type	Source
15350213	PubMed citation	Europe PMC

Last Modified

21 November 2014