Showing metabocard for Cis-4-Carboxymethylenebut-2-en-4-olide (MMDBc0030050)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:52:03 UTC
Update Date2024-04-30 19:44:22 UTC
Metabolite IDMMDBc0030050
Metabolite Identification
Common NameCis-4-Carboxymethylenebut-2-en-4-olide
DescriptionCis-4-carboxymethylenebut-2-en-4-olide is a member of the chemical class known as Furans. These are compounds containing a furan ring, which is a five-member aromatic ring with one oxygen atom, four carbon atoms.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb101cc760>

 
  Mrv0541 02241222082D          
 
 10 10  0  0  0  0            999 V2000
   15.8233  -12.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4858  -12.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0731  -13.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0395  -12.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1559  -12.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8984  -13.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9358  -12.7321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3259  -13.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3259  -13.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6123  -12.7321    0.0000 O   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
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  6  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb101cc760>

HMDB0060459
     RDKit          3D
cis-4-Carboxymethylenebut-2-en-4-olide
 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.9180   -1.3180    0.6526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0999   -0.2466    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4617    0.0856   -0.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    0.6259   -0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    0.3553   -0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -0.7882    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -0.6985    0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869    0.5243   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6724    0.8950   -0.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105    1.1395   -0.6967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8194    0.9606    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385    1.5199   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697   -1.6169    0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963   -1.4380    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10  5  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  7 14  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb101cc760>

 
  Mrv0541 02241222082D          
 
 10 10  0  0  0  0            999 V2000
   15.8233  -12.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4858  -12.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0731  -13.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0395  -12.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1559  -12.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8984  -13.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9358  -12.7321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3259  -13.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3259  -13.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6123  -12.7321    0.0000 O   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
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  6  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030050

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)\C=C1\OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)/b4-3+

> <INCHI_KEY>
AYFXPGXAZMFWNH-ONEGZZNKSA-N

> <FORMULA>
C6H4O4

> <MOLECULAR_WEIGHT>
140.0936

> <EXACT_MASS>
140.010958616

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
11.912014006023167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E)-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.18295978666666662

> <ALOGPS_LOGS>
-0.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0646434995810767

> <JCHEM_PKA_STRONGEST_BASIC>
-6.947904211705147

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
33.325700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2E)-5-oxofuran-2-ylidene]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb101cc760>

HMDB0060459
     RDKit          3D
cis-4-Carboxymethylenebut-2-en-4-olide
 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.9180   -1.3180    0.6526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0999   -0.2466    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4617    0.0856   -0.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    0.6259   -0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    0.3553   -0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -0.7882    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -0.6985    0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869    0.5243   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6724    0.8950   -0.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105    1.1395   -0.6967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8194    0.9606    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385    1.5199   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697   -1.6169    0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963   -1.4380    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10  5  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  7 14  1  0
M  END
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PDB for #<Metabolite:0x00007fdb101cc760>

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      29.537 -24.247   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      30.774 -23.350   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      30.003 -25.717   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.074 -23.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.024 -24.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.544 -25.717   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      33.480 -23.767   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      26.742 -24.536   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      26.742 -26.074   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      25.410 -23.767   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    8                                                       
CONECT    5    2    7    6                                                  
CONECT    6    3    5                                                       
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
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:0x00007fdb101cc760>

COMPND    HMDB0060459
HETATM    1  O1  UNL     1      -1.918  -1.318   0.653  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.100  -0.247   0.023  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.462   0.086  -0.206  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.055   0.626  -0.459  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.219   0.355  -0.268  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.799  -0.788   0.414  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.139  -0.698   0.397  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.487   0.524  -0.308  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.672   0.895  -0.493  1.00  0.00           O  
HETATM   10  O4  UNL     1       1.310   1.139  -0.697  1.00  0.00           O  
HETATM   11  H1  UNL     1      -3.819   0.961   0.202  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.338   1.520  -0.987  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.270  -1.617   0.884  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.796  -1.438   0.845  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   12
CONECT    5    6   10
CONECT    6    7    7   13
CONECT    7    8   14
CONECT    8    9    9   10
END
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SMILES for #<Metabolite:0x00007fdb101cc760>

OC(=O)\C=C1\OC(=O)C=C1
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INCHI for #<Metabolite:0x00007fdb101cc760>

InChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)/b4-3+
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Synonyms
ValueSource
(5-oxo-2(5H)-Furanylidene)acetic acidChEBI
4-Carboxymethylenebut-2-en-4-olideChEBI
(5-oxo-2(5H)-Furanylidene)acetateGenerator
DienelactoneMeSH
cis-DienelactoneMeSH
Molecular FormulaC6H4O4
Average Mass140.0936
Monoisotopic Mass140.010958616
IUPAC Name2-[(2E)-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid
Traditional Name[(2E)-5-oxofuran-2-ylidene]acetic acid
CAS Registry Number73237-79-3
SMILES
OC(=O)\C=C1\OC(=O)C=C1
InChI Identifier
InChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)/b4-3+
InChI KeyAYFXPGXAZMFWNH-ONEGZZNKSA-N