Autoinducer 2

HCID 446576
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Basic information

Standard SMILES
C[C@]12OC[C@H](O)[C@@]1(O)O[B-](O)(O)O2
InChIKey
ACKRRKSNOOISSG-VPENINKCSA-N
Molecular formula
C5H10BO7-
Average molar mass
192.94 g/mol
Monoisotopic mass
193.05250664

Overview

Autoinducer-2 is an organic anion that is a borate diester derived from a furanose and acts a universal signal molecule mediating intra- and interspecies communication among bacteria. It has a role as an autoinducer and a bacterial metabolite.

Names & identifiers

Preferred name
Autoinducer 2
IUPAC
(1R,5S,8S)-3,3-dihydroxy-5-methyl-2,4,6-trioxa-3-boranuidabicyclo[3.3.0]octane-1,8-diol

Names & synonyms

Autoinducer-2Autoinducer 2CHEBI:40646DTXSID201027132(1R,5S,8S)-3,3-dihydroxy-5-methyl-2,4,6-trioxa-3-boranuidabicyclo[3.3.0]octane-1,8-diol406683-36-1DTXSID201028330(1R,5S,8S)-3,3-dihydroxy-5-methyl-2,4,6-trioxa-3-boranuidabicyclo(3.3.0)octane-1,8-diolRefChem:1077359DTXCID001838406DTXCID401513911(4S)-4,5-Dihydroxy-2,3-pentanedione
Show more names
AI-2(1R,2S,5S)-7,7-Dihydroxy-5-methyl-4,6,8-trioxa-7-boranuidabicyclo[3.3.0]octane-1,2-diol3A-METHYL-5,6-DIHYDRO-FURO[2,3-D][1,3,2]DIOXABOROLE-2,2,6,6A-TETRAOLAI2Autoinducer IIAI-2 autoinducer(S)-THMF-borateAI-2 (vibrio)

Database identifiers

PubChem CID
446576
DTXSID
DTXSID201027132
ChEMBL
CHEMBL1230903
ChEBI
CHEBI:40646
Nikkaji
J2.048.999E

Properties

Computed structural properties

Topological polar surface area
109 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
8
Rotatable bonds
0
Heavy atoms
13

Related reactions

2 records
New reaction record

Compound notes

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