Showing metabocard for 4-Fumarylacetoacetic acid (MMDBc0047925)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:15:47 UTC
Update Date2024-04-30 20:32:41 UTC
Metabolite IDMMDBc0047925
Metabolite Identification
Common Name4-Fumarylacetoacetic acid
Description4-Fumarylacetoacetic acid is an intermediate in the metabolism of tyrosine. Fumarylacetoacetate hydrolase (FAH) is an enzyme which catalyzes the hydrolysis of 4-fumarylacetoacetate into fumarate and acetoacetate. FAH is the last enzyme in the tyrosine catabolism pathway. FAH deficiency is associated with Type 1 hereditary tyrosinemia.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe279d4a2e8>


  Mrv1652309042000202D          

 14 13  0  0  0  0            999 V2000
10009.830310008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.114810008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.400710008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.686010008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.970910008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.256210008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.541510008.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.256210009.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.400710007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.546010008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.259510008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.975010008.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.259510007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.830310007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  1 14  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fe279d4a2e8>

HMDB0001268
     RDKit          3D
4-Fumarylacetoacetic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
    4.3209    0.0376   -1.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1756    0.0797   -0.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2881    0.3500    0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895   -0.1406    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7627   -0.3988   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -0.6177    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181   -0.5952    1.4731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -0.8844   -0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -1.0632    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3754   -2.1702    0.3769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5976    0.1196    0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5465    0.7624   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7072    0.3018   -1.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632    1.8769    0.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745    1.2868    0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102   -0.0983    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081   -0.4461   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8361   -0.1045   -1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754   -1.8529   -1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169   -0.1524    1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.8829    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9089    2.8265    0.1275 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
  8 19  1  0
 11 20  1  0
 11 21  1  0
 14 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fe279d4a2e8>


  Mrv1652309042000202D          

 14 13  0  0  0  0            999 V2000
10009.830310008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.114810008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.400710008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.686010008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.970910008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.256210008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.541510008.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.256210009.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.400710007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.546010008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.259510008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.975010008.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.259510007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.830310007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  1 14  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047925

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1+

> <INCHI_KEY>
GACSIVHAIFQKTC-OWOJBTEDSA-N

> <FORMULA>
C8H8O6

> <MOLECULAR_WEIGHT>
200.1455

> <EXACT_MASS>
200.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.284079207301815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-4,6-dioxooct-2-enedioic acid

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
0.4027936060000003

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.8947874187334905

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0462803866743133

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057634181873521

> <JCHEM_POLAR_SURFACE_AREA>
108.74000000000001

> <JCHEM_REFRACTIVITY>
44.3974

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-fumarylacetoacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fe279d4a2e8>

HMDB0001268
     RDKit          3D
4-Fumarylacetoacetic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
    4.3209    0.0376   -1.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1756    0.0797   -0.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2881    0.3500    0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895   -0.1406    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7627   -0.3988   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -0.6177    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181   -0.5952    1.4731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078   -0.8844   -0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -1.0632    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3754   -2.1702    0.3769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5976    0.1196    0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5465    0.7624   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7072    0.3018   -1.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632    1.8769    0.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745    1.2868    0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102   -0.0983    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081   -0.4461   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8361   -0.1045   -1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754   -1.8529   -1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169   -0.1524    1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.8829    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9089    2.8265    0.1275 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
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
  8 19  1  0
 11 20  1  0
 11 21  1  0
 14 22  1  0
M  END
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PDB for #<Metabolite:0x00007fe279d4a2e8>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8685.0178682.603   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8683.6818683.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8682.3488682.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8681.0148683.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8679.6798682.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8678.3458683.373   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8677.0118682.603   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8678.3458684.912   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8682.3488681.063   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8686.3538683.373   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8687.6848682.603   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8689.0208683.373   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8687.6848681.063   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8685.0178681.063   0.000  0.00  0.00           O+0
CONECT    1    2   10   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
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3D PDB for #<Metabolite:0x00007fe279d4a2e8>

COMPND    HMDB0001268
HETATM    1  O1  UNL     1       4.321   0.038  -1.672  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.176   0.080  -0.428  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.288   0.350   0.349  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.890  -0.141   0.232  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.763  -0.399  -0.428  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.488  -0.618   0.225  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.318  -0.595   1.473  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.708  -0.884  -0.612  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.929  -1.063   0.193  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.375  -2.170   0.377  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.598   0.120   0.769  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.546   0.762  -0.182  1.00  0.00           C  
HETATM   13  O5  UNL     1      -3.707   0.302  -1.341  1.00  0.00           O  
HETATM   14  O6  UNL     1      -4.263   1.877   0.202  1.00  0.00           O  
HETATM   15  H1  UNL     1       5.575   1.287   0.604  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.810  -0.098   1.309  1.00  0.00           H  
HETATM   17  H3  UNL     1       1.808  -0.446  -1.502  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.836  -0.104  -1.393  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.475  -1.853  -1.137  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.217  -0.152   1.669  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.871   0.883   1.169  1.00  0.00           H  
HETATM   22  H8  UNL     1      -3.909   2.826   0.127  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5    5   16
CONECT    5    6   17
CONECT    6    7    7    8
CONECT    8    9   18   19
CONECT    9   10   10   11
CONECT   11   12   20   21
CONECT   12   13   13   14
CONECT   14   22
END
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SMILES for #<Metabolite:0x00007fe279d4a2e8>

OC(=O)CC(=O)CC(=O)\C=C\C(O)=O
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INCHI for #<Metabolite:0x00007fe279d4a2e8>

InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1+
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Synonyms
ValueSource
FumarylacetoacetoneChEBI
FumarylacetoacetateKegg
Fumarylacetoacetic acidGenerator
4-FumarylacetoacetateGenerator
4-Fumaryl-acetoacetateHMDB
(2E)-4,6-Dioxo-2-octenedioic acidHMDB
4-Fumarylacetoacetic acidHMDB
Molecular FormulaC8H8O6
Average Mass200.1455
Monoisotopic Mass200.032087988
IUPAC Name(2E)-4,6-dioxooct-2-enedioic acid
Traditional Name4-fumarylacetoacetic acid
CAS Registry Number28613-33-4
SMILES
OC(=O)CC(=O)CC(=O)\C=C\C(O)=O
InChI Identifier
InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1+
InChI KeyGACSIVHAIFQKTC-OWOJBTEDSA-N