Showing metabocard for 4-Fluoromuconolactone (MMDBc0051932)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-05-16 20:40:42 UTC
Update Date2024-04-30 20:43:06 UTC
Metabolite IDMMDBc0051932
Metabolite Identification
Common Name4-Fluoromuconolactone
Description4-Fluoromuconolactone belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 4-Fluoromuconolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Fluoromuconolactone exists in all living organisms, ranging from bacteria to humans. These are dihydrofurans with a carbonyk group at the C2 carbon atom.
Structure
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa5095c17e0>


  Mrv0541 05161317582D          

 11 11  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    3.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579    2.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 11  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fa5095c17e0>

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3D SDF for #<Metabolite:0x00007fa5095c17e0>

  Mrv0541 05161317582D          

 11 11  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    3.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579    2.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 11  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0051932

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CC1(F)OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H5FO4/c7-6(3-4(8)9)2-1-5(10)11-6/h1-2H,3H2,(H,8,9)

> <INCHI_KEY>
JWTRAEIUKUKVDW-UHFFFAOYSA-N

> <FORMULA>
C6H5FO4

> <MOLECULAR_WEIGHT>
160.0999

> <EXACT_MASS>
160.017186853

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.473710134210563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-fluoro-5-oxo-2,5-dihydrofuran-2-yl)acetic acid

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
0.8820255106666667

> <ALOGPS_LOGS>
-0.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.42342052270588

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6954905095724415

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9117427416185855

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
31.788000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.94e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-fluoromuconolactone

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for #<Metabolite:0x00007fa5095c17e0>
https://cactus.nci.nih.gov/chemical/structure/OC(=O)CC1(F)OC(=O)C=C1/file?for...
 OpenBabel09142113323D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:15})
 16 16  0  0  0  0  0  0  0  0999 V2000
    3.2647    0.5315   -0.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201    0.2785   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9824    0.6481    0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068   -0.4666   -0.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751   -0.6209    0.0834 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2475   -1.2192    1.2754 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703    0.6784    0.3584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0480    0.6377   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8376    1.5584    0.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -0.6806   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616   -1.4512   -0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9499    1.0123   -0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6889    0.0902   -1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3614   -1.4523   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981   -0.9816   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761   -2.4733   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
M  END
$$$$

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PDB for #<Metabolite:0x00007fa5095c17e0>
HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.614   4.689   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  F   UNK     0       0.029   3.224   0.000  0.00  0.00           F+0
HETATM    8  O   UNK     0       2.645   5.834   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.108   5.009   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    6                                                       
CONECT    4    3    8    9                                                  
CONECT    5    1   10   11                                                  
CONECT    6    2    3    7   11                                             
CONECT    7    6                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    5    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for #<Metabolite:0x00007fa5095c17e0>
COMPND    https://cactus.nci.nih.gov/chemical/structure/OC(=O)CC1(F)OC(=O)C=C1/file?for... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  O   UNL     1       3.265   0.531  -0.840  1.00  0.00           O  
HETATM    2  C   UNL     1       2.120   0.279  -0.186  1.00  0.00           C  
HETATM    3  O   UNL     1       1.982   0.648   0.956  1.00  0.00           O  
HETATM    4  C   UNL     1       1.007  -0.467  -0.876  1.00  0.00           C  
HETATM    5  C   UNL     1      -0.175  -0.621   0.083  1.00  0.00           C  
HETATM    6  F   UNL     1       0.247  -1.219   1.275  1.00  0.00           F  
HETATM    7  O   UNL     1      -0.770   0.678   0.358  1.00  0.00           O  
HETATM    8  C   UNL     1      -2.048   0.638  -0.063  1.00  0.00           C  
HETATM    9  O   UNL     1      -2.838   1.558   0.013  1.00  0.00           O  
HETATM   10  C   UNL     1      -2.346  -0.681  -0.630  1.00  0.00           C  
HETATM   11  C   UNL     1      -1.262  -1.451  -0.559  1.00  0.00           C  
HETATM   12  H   UNL     1       3.950   1.012  -0.355  1.00  0.00           H  
HETATM   13  H   UNL     1       0.689   0.090  -1.757  1.00  0.00           H  
HETATM   14  H   UNL     1       1.361  -1.452  -1.177  1.00  0.00           H  
HETATM   15  H   UNL     1      -3.298  -0.982  -1.041  1.00  0.00           H  
HETATM   16  H   UNL     1      -1.176  -2.473  -0.897  1.00  0.00           H  
CONECT    1    2   12                                                 
CONECT    2    1    3    3    4                                       
CONECT    3    2    2                                                 
CONECT    4    2    5   13   14                                       
CONECT    5    4    6    7   11                                       
CONECT    6    5                                                      
CONECT    7    5    8                                                 
CONECT    8    7    9    9   10                                       
CONECT    9    8    8                                                 
CONECT   10    8   11   11   15                                       
CONECT   11   10   10    5   16                                       
CONECT   12    1                                                      
CONECT   13    4                                                      
CONECT   14    4                                                      
CONECT   15   10                                                      
CONECT   16   11                                                      
MASTER        0    0    0    0    0    0    0    0   16    0   16    0
END

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SMILES for #<Metabolite:0x00007fa5095c17e0>
OC(=O)CC1(F)OC(=O)C=C1
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INCHI for #<Metabolite:0x00007fa5095c17e0>
InChI=1S/C6H5FO4/c7-6(3-4(8)9)2-1-5(10)11-6/h1-2H,3H2,(H,8,9)
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Synonyms
ValueSource
4-Carboxymethyl-4-fluorobut-2-en-4-olideHMDB
Molecular FormulaC6H5FO4
Average Mass160.0999
Monoisotopic Mass160.017186853
IUPAC Name2-(2-fluoro-5-oxo-2,5-dihydrofuran-2-yl)acetic acid
Traditional Name4-fluoromuconolactone
CAS Registry NumberNot Available
SMILES
OC(=O)CC1(F)OC(=O)C=C1
InChI Identifier
InChI=1S/C6H5FO4/c7-6(3-4(8)9)2-1-5(10)11-6/h1-2H,3H2,(H,8,9)
InChI KeyJWTRAEIUKUKVDW-UHFFFAOYSA-N