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Showing metabocard for fluorobenzoylpropionic acid (HMDB0060951)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:09:08 UTC
Update Date2019-07-23 07:15:27 UTC
HMDB IDHMDB0060951
Secondary Accession Numbers
  • HMDB60951
Metabolite Identification
Common Namefluorobenzoylpropionic acid
Descriptionfluorobenzoylpropionic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. It is in the butyrophenone class of antipsychotic medications and has pharmacological effects similar to the phenothiazines. fluorobenzoylpropionic acid is a metabolite of haloperidol. fluorobenzoylpropionic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Haloperidol is a typical antipsychotic. Haloperidol is an older antipsychotic used in the treatment of schizophrenia and acute psychotic states and delirium.
Structure
Data?1563866127
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060951 (fluorobenzoylpropionic acid)

  Mrv0541 07091309092D          

 15 15  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    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
  6  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  2  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
M  END
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3D MOL for HMDB0060951 (fluorobenzoylpropionic acid)

HMDB0060951
     RDKit          3D
fluorobenzoylpropionic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    3.8376   -0.0622    0.9130 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397    0.5439   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    1.4491   -0.6914 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    0.2620   -0.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801   -0.7439    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612   -1.0970   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196   -1.9083   -1.4505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0965   -0.5643    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274    0.3258    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128    0.8167    1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    0.4330    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6872    0.9255    1.5081 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5136   -0.4529   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7077   -0.8143   -0.5539 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3005   -0.9460   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7766    2.1960   -0.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3148   -0.0135   -1.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    1.2227   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -0.4153    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -1.6917    0.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1939    0.6543    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935    1.5219    2.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699   -1.6414   -1.3399 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15  8  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  9 21  1  0
 10 22  1  0
 15 23  1  0
M  END
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3D SDF for HMDB0060951 (fluorobenzoylpropionic acid)

  Mrv0541 07091309092D          

 15 15  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    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
  6  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  2  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060951

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCC(=O)C1=CC(F)=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H8F2O3/c11-7-2-1-6(5-8(7)12)9(13)3-4-10(14)15/h1-2,5H,3-4H2,(H,14,15)

> <INCHI_KEY>
GYDFFFKCUNUZEL-UHFFFAOYSA-N

> <FORMULA>
C10H8F2O3

> <MOLECULAR_WEIGHT>
214.1655

> <EXACT_MASS>
214.044150532

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.21284195492023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3,4-difluorophenyl)-4-oxobutanoic acid

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.6411599543333333

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.74066365049092

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3355255252814

> <JCHEM_PKA_STRONGEST_BASIC>
-7.468205926400451

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
47.78690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,4-difluorophenyl)-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0060951 (fluorobenzoylpropionic acid)

HMDB0060951
     RDKit          3D
fluorobenzoylpropionic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    3.8376   -0.0622    0.9130 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397    0.5439   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    1.4491   -0.6914 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    0.2620   -0.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801   -0.7439    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612   -1.0970   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196   -1.9083   -1.4505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0965   -0.5643    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274    0.3258    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128    0.8167    1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    0.4330    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6872    0.9255    1.5081 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5136   -0.4529   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7077   -0.8143   -0.5539 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3005   -0.9460   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7766    2.1960   -0.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3148   -0.0135   -1.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    1.2227   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -0.4153    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -1.6917    0.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1939    0.6543    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935    1.5219    2.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699   -1.6414   -1.3399 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15  8  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  9 21  1  0
 10 22  1  0
 15 23  1  0
M  END
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PDB for HMDB0060951 (fluorobenzoylpropionic acid)

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   11  F   UNK     0       5.335   7.700   0.000  0.00  0.00           F+0
HETATM   12  F   UNK     0       2.667   9.240   0.000  0.00  0.00           F+0
HETATM   13  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6    8                                                       
CONECT    6    1    5    9                                                  
CONECT    7    2    8   11                                                  
CONECT    8    5    7   12                                                  
CONECT    9    3    6   13                                                  
CONECT   10    4   14   15                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END
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3D PDB for HMDB0060951 (fluorobenzoylpropionic acid)

COMPND    HMDB0060951
HETATM    1  O1  UNL     1       3.838  -0.062   0.913  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.540   0.544  -0.144  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.445   1.449  -0.691  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.224   0.262  -0.765  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.480  -0.744   0.042  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.161  -1.097  -0.486  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.120  -1.908  -1.451  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.096  -0.564   0.041  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.127   0.326   1.093  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.313   0.817   1.576  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.516   0.433   1.022  1.00  0.00           C  
HETATM   12  F1  UNL     1      -4.687   0.925   1.508  1.00  0.00           F  
HETATM   13  C9  UNL     1      -3.514  -0.453  -0.027  1.00  0.00           C  
HETATM   14  F2  UNL     1      -4.708  -0.814  -0.554  1.00  0.00           F  
HETATM   15  C10 UNL     1      -2.300  -0.946  -0.510  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.777   2.196  -0.063  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.315  -0.014  -1.835  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.645   1.223  -0.705  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.478  -0.415   1.101  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.097  -1.692   0.037  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.194   0.654   1.558  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.294   1.522   2.412  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.370  -1.641  -1.340  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7    7    8
CONECT    8    9    9   15
CONECT    9   10   21
CONECT   10   11   11   22
CONECT   11   12   13
CONECT   13   14   15   15
CONECT   15   23
END
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SMILES for HMDB0060951 (fluorobenzoylpropionic acid)

OC(=O)CCC(=O)C1=CC(F)=C(F)C=C1
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INCHI for HMDB0060951 (fluorobenzoylpropionic acid)

InChI=1S/C10H8F2O3/c11-7-2-1-6(5-8(7)12)9(13)3-4-10(14)15/h1-2,5H,3-4H2,(H,14,15)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
FluorobenzoylpropionateGenerator
4-(3,4-Difluorophenyl)-4-oxobutanoateGenerator
Chemical FormulaC10H8F2O3
Average Molecular Weight214.1655
Monoisotopic Molecular Weight214.044150532
IUPAC Name4-(3,4-difluorophenyl)-4-oxobutanoic acid
Traditional Name4-(3,4-difluorophenyl)-4-oxobutanoic acid
CAS Registry Number84313-94-0
SMILES
OC(=O)CCC(=O)C1=CC(F)=C(F)C=C1
InChI Identifier
InChI=1S/C10H8F2O3/c11-7-2-1-6(5-8(7)12)9(13)3-4-10(14)15/h1-2,5H,3-4H2,(H,14,15)
InChI KeyGYDFFFKCUNUZEL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Benzoyl
  • Aryl alkyl ketone
  • Gamma-keto acid
  • Fluorobenzene
  • Halobenzene
  • Keto acid
  • Aryl fluoride
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organohalogen compound
  • Organofluoride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2758337
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available