ECMDB: autoinducer 2 (ECMDB24232) (M2MDB006349)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (1)

Record Information

Version

2.0

Creation Date

2015-09-08 17:50:19 -0600

Update Date

2015-09-14 16:46:41 -0600

Secondary Accession Numbers

ECMDB24232

Identification

Name:

autoinducer 2

Description

Autoinducer 2 (AI-2), a furanosyl borate diester, is a member of a family of signaling molecules used in quorum sensing. AI-2 is unique in that it is one of only a few known biomolecules incorporating boron. First identified in the marine bacterium Vibrio harveyi, AI-2 is produced and recognized by many Gram-negative and Gram-positive bacteria. AI-2 is synthesized by the reaction of 1-deoxy-3-dehydro-D-ribulose with boric acid and is recognized by the two-component sensor kinase LuxPQ in Vibrionaceae (Wikipedia).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

Value	Source
1-Deoxypentosone	MeSH
4,5-Dihydroxypentane-2,3-dione	MeSH
DPD AI-2 precursor	MeSH
4,5-DHP	MeSH

Chemical Formula:

C₅H₈O₄

Weight:

Average: 132.115
Monoisotopic: 132.042258738

InChI Key:

UYTRITJAZOPLCZ-UHFFFAOYSA-N

InChI:

InChI=1S/C5H8O4/c1-3(7)5(9)4(8)2-6/h4,6,8H,2H2,1H3

CAS number:

Not Available

IUPAC Name:

4,5-dihydroxypentane-2,3-dione

Traditional IUPAC Name:

4,5-dihydroxy-2,3-pentanedione

SMILES:

CC(=O)C(=O)C(O)CO

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

Monosaccharide
Beta-hydroxy ketone
Alpha-diketone
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
1,2-diol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a small molecule (DIHYDROXYPENTANEDIONE )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	272 g/L	ALOGPS
logP	-0.95	ALOGPS
logP	-0.9	ChemAxon
logS	0.31	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	29.28 m³·mol⁻¹	ChemAxon
Polarizability	12.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

S-ribosyl-L-homocysteine + S-ribosyl-L-homocysteine > Homocysteine + autoinducer 2 + Homocysteine + autoinducer 2

SMPDB Pathways:

Quorum Sensing	PW000836
S-adenosyl-L-methionine cycle	PW002080

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-3900000000-c3606a0de0753ee55e3a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03xs-9300000000-5983224a4b111e5924f5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btc-9000000000-85c056bb028337d6565a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0089-9700000000-c58778f342acf421218f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-059i-9200000000-b0bb1b99ccfc328190ed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-2cd2700615652d11591b	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	443434
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Autoinducer-2
BioCyc ID	Not Available

Enzymes

Protein Details

1. S-ribosylhomocysteine lyase

General function:: Involved in catalytic activity
Specific function:: Involved in the synthesis of autoinducer 2 (AI-2) which is secreted by bacteria and is used to communicate both the cell density and the metabolic potential of the environment. The regulation of gene expression in response to changes in cell density is called quorum sensing. Catalyzes the transformation of S-ribosylhomocysteine (RHC) to homocysteine (HC) and 4,5- dihydroxy-2,3-pentadione (DPD)
Gene Name:: luxS
Uniprot ID:: P45578
Molecular weight:: 19416

Reactions

S-(5-deoxy-D-ribos-5-yl)-L-homocysteine = L-homocysteine + (4S)-4,5-dihydroxypentan-2,3-dione.

autoinducer 2 (ECMDB24232) (M2MDB006349)

Structure for #<Compound:0xb24cc2d4>

Enzymes

Reactions