Showing metabocard for (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran (MMDBc0030347)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:04:35 UTC
Update Date2022-08-31 17:44:04 UTC
Metabolite IDMMDBc0030347
Metabolite Identification
Common Name(2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran
Description(2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran, also known as autoinducer 2 (AI-2), is a member of the chemical class known as Oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. AI-2 is the R isomer of 2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran, so it can be abbreviated as (R)-THMF. Autoinducer 2 (AI-2), a quorum sensing signaling molecule proposed to be involved in interspecies communication, is produced by many species of gram-negative and gram-positive bacteria including E. coli. (PMID 19636340 , 15601708 , 18256823 ) AI-2 is spontaneously derived from 4,5-dihydroxy-2,3-pentanedione that, along with homocysteine, is produced by cleavage of S-adenosylhomocysteine (SAH) and S-ribosylhomocysteine by the Pfs and LuxS enzymes. (PMID 16885435 ) Both LsrB and Tsr are necessary for sensing AI-2. LsrB binds AI-2 in the periplasm, and Tsr is the L-serine chemoreceptor. (PMID 21097621 )
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fecaa1655a0>


  Mrv0541 04051517282D          

 10 10  0  0  0  0            999 V2000
    1.1197    1.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677    1.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    0.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9802   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996    0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8533    0.2938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5121    1.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fecaa1655a0>

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3D SDF for #<Metabolite:0x00007fecaa1655a0>

  Mrv0541 04051517282D          

 10 10  0  0  0  0            999 V2000
    1.1197    1.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677    1.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    0.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9802   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996    0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8533    0.2938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5121    1.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030347

> <DATABASE_NAME>
MIME

> <SMILES>
CC1(O)OCC(O)C1(O)O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O5/c1-4(7)5(8,9)3(6)2-10-4/h3,6-9H,2H2,1H3

> <INCHI_KEY>
BVIYGXUQVXBHQS-UHFFFAOYSA-N

> <FORMULA>
C5H10O5

> <MOLECULAR_WEIGHT>
150.13

> <EXACT_MASS>
150.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.340115195693922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyloxolane-2,3,3,4-tetrol

> <ALOGPS_LOGP>
-1.96

> <JCHEM_LOGP>
-1.6134906500000001

> <ALOGPS_LOGS>
0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.86859835924774

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.158563777105503

> <JCHEM_PKA_STRONGEST_BASIC>
-3.971174517344722

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
30.487499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.66e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyloxolane-2,3,3,4-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fecaa1655a0>
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PDB for #<Metabolite:0x00007fecaa1655a0>
HEADER    PROTEIN                                 05-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-APR-15         0                                  
HETATM    1  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.029   3.224   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.593   0.548   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.956   2.508   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    8                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10    2                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for #<Metabolite:0x00007fecaa1655a0>
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SMILES for #<Metabolite:0x00007fecaa1655a0>
CC1(O)OCC(O)C1(O)O
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INCHI for #<Metabolite:0x00007fecaa1655a0>
InChI=1S/C5H10O5/c1-4(7)5(8,9)3(6)2-10-4/h3,6-9H,2H2,1H3
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Synonyms
ValueSource
THMF SugarMeSH
2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuranMeSH
Molecular FormulaC5H10O5
Average Mass150.13
Monoisotopic Mass150.052823422
IUPAC Name2-methyloxolane-2,3,3,4-tetrol
Traditional Name2-methyloxolane-2,3,3,4-tetrol
CAS Registry NumberNot Available
SMILES
CC1(O)OCC(O)C1(O)O
InChI Identifier
InChI=1S/C5H10O5/c1-4(7)5(8,9)3(6)2-10-4/h3,6-9H,2H2,1H3
InChI KeyBVIYGXUQVXBHQS-UHFFFAOYSA-N