Showing metabocard for Homoserine lactone (MMDBc0030194)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:57:51 UTC
Update Date2022-08-31 17:40:35 UTC
Metabolite IDMMDBc0030194
Metabolite Identification
Common NameHomoserine lactone
DescriptionN-Acyl homoserine lactones (AHLs or N-AHLs) are a class of signaling molecules involved in bacterial quorum sensing. Quorum sensing is a method of communication between bacteria that enables the coordination of group based behavior based on population density. They signal changes in gene expression, such as switching between the flagella gene and the gene for pili for the development of a biofilm.One example of the involvement of AHLs in quorum sensing is in the regulation of the bioluminescent protein luciferase in the luminescent bacteria Vibrio fischeri. Similar pathways occur in other luminescent bacteria. In Vibrio fischeri, when the concentration of AHLs exceeds a certain limit, the transcription of the operon luxAB begins. Transcription of the operon results in luminescence due to the expression of LuxA and LuxB, which form a protein known as luciferase. This is an important feature of quorum sensing, as it makes little sense for one cell to waste the energy producing light, as the resulting light will be so faint it will be more or less undetectable. Instead, once the bacterial population has reached a specific size, only then does light production commence.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9250857390>

Structure #1
  Mrv0541 02241207322D          

  8  7  0  0  0  0            999 V2000
    0.8749   -0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6199   -0.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    1.2413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    0.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -0.8533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9250857390>

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3D SDF for #<Metabolite:0x00007f9250857390>
Structure #1
  Mrv0541 02241207322D          

  8  7  0  0  0  0            999 V2000
    0.8749   -0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6199   -0.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600   -0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    1.2413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    0.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -0.8533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030194

> <DATABASE_NAME>
MIME

> <SMILES>
Br.NC1CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO2.BrH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H

> <INCHI_KEY>
MKLNTBLOABOJFZ-UHFFFAOYSA-N

> <FORMULA>
C4H8BrNO2

> <MOLECULAR_WEIGHT>
182.016

> <EXACT_MASS>
180.973841152

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.466685504889117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-aminooxolan-2-one hydrobromide

> <JCHEM_LOGP>
-0.9011904176666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.329657478497863

> <JCHEM_POLAR_SURFACE_AREA>
52.32000000000001

> <JCHEM_REFRACTIVITY>
23.414200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
HSLs hydrobromide

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9250857390>
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PDB for #<Metabolite:0x00007f9250857390>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.633  -0.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.157  -1.593   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.387   0.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.859  -0.128   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.387   2.317   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      -2.323   0.348   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.383  -1.593   0.000  0.00  0.00           O+0
HETATM    8 Br   UNK     0       5.813   0.000   0.000  0.00  0.00          Br+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    4    5                                                  
CONECT    4    3    6    7                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7    2    4                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for #<Metabolite:0x00007f9250857390>
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SMILES for #<Metabolite:0x00007f9250857390>
Br.NC1CCOC1=O
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INCHI for #<Metabolite:0x00007f9250857390>
InChI=1S/C4H7NO2.BrH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H
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SynonymsNot Available
Molecular FormulaC4H8BrNO2
Average Mass182.016
Monoisotopic Mass180.973841152
IUPAC Name3-aminooxolan-2-one hydrobromide
Traditional NameHSLs hydrobromide
CAS Registry Number1192-20-7
SMILES
Br.NC1CCOC1=O
InChI Identifier
InChI=1S/C4H7NO2.BrH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H
InChI KeyMKLNTBLOABOJFZ-UHFFFAOYSA-N