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Showing metabocard for alpha-Fluoro-beta-ureidopropionic acid (HMDB0060435)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:20:39 UTC
Update Date2023-02-21 17:29:59 UTC
HMDB IDHMDB0060435
Secondary Accession Numbers
  • HMDB60435
Metabolite Identification
Common Namealpha-Fluoro-beta-ureidopropionic acid
Descriptionalpha-Fluoro-beta-ureidopropionic acid is a metabolite of fluorouracil. Fluorouracil (5-FU or f5U) (sold under the brand names Adrucil, Carac, Efudix, Efudex and Fluoroplex) is a drug that is a pyrimidine analog which is used in the treatment of cancer. It is a suicide inhibitor and works through irreversible inhibition of thymidylate synthase. It belongs to the family of drugs called antimetabolites. It is typically administered with leucovorin. (Wikipedia)
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060435 (alpha-Fluoro-beta-ureidopropionic acid)

 
  Mrv1652303121904252D          

 10  9  0  0  0  0            999 V2000
   14.2984  -13.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0129  -13.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7274  -13.5762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4419  -13.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1564  -13.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8708  -13.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5853  -13.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8708  -12.3389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1564  -14.4012    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0129  -12.3387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  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  2  0  0  0  0
  5  9  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
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3D MOL for HMDB0060435 (alpha-Fluoro-beta-ureidopropionic acid)

HMDB0060435
     RDKit          3D
alpha-Fluoro-beta-ureidopropionic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    2.5425    1.3837    0.2284 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3205    0.1473    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -0.7277    0.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321   -0.2635    0.9101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1106    0.0215    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740   -0.5156    0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2140   -1.8734    0.8611 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5794   -0.2051   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139   -1.1173   -0.4875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607    1.0989   -0.3062 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865    2.0663    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4142   -1.6335    0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9036   -0.7632    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709   -0.4772   -0.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1729    1.1114   -0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4427   -0.0905    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028    1.8378   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
 10 17  1  0
M  END
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3D SDF for HMDB0060435 (alpha-Fluoro-beta-ureidopropionic acid)

 
  Mrv1652303121904252D          

 10  9  0  0  0  0            999 V2000
   14.2984  -13.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0129  -13.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7274  -13.5762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4419  -13.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1564  -13.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8708  -13.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5853  -13.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8708  -12.3389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1564  -14.4012    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0129  -12.3387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  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  2  0  0  0  0
  5  9  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060435

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)NCC(F)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7FN2O3/c5-2(3(8)9)1-7-4(6)10/h2H,1H2,(H,8,9)(H3,6,7,10)

> <INCHI_KEY>
FKTHAKABFGARQH-UHFFFAOYSA-N

> <FORMULA>
C4H7FN2O3

> <MOLECULAR_WEIGHT>
150.1084

> <EXACT_MASS>
150.044070305

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.135504956247186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(carbamoylamino)-2-fluoropropanoic acid

> <ALOGPS_LOGP>
-1.07

> <JCHEM_LOGP>
-1.2492284379999998

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.603009282847257

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5232520193623076

> <JCHEM_PKA_STRONGEST_BASIC>
-2.169397352918537

> <JCHEM_POLAR_SURFACE_AREA>
92.42

> <JCHEM_REFRACTIVITY>
28.4694

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(carbamoylamino)-2-fluoropropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0060435 (alpha-Fluoro-beta-ureidopropionic acid)

HMDB0060435
     RDKit          3D
alpha-Fluoro-beta-ureidopropionic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    2.5425    1.3837    0.2284 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3205    0.1473    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -0.7277    0.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321   -0.2635    0.9101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1106    0.0215    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740   -0.5156    0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2140   -1.8734    0.8611 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5794   -0.2051   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139   -1.1173   -0.4875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607    1.0989   -0.3062 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865    2.0663    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4142   -1.6335    0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9036   -0.7632    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709   -0.4772   -0.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1729    1.1114   -0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4427   -0.0905    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028    1.8378   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
 10 17  1  0
M  END
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PDB for HMDB0060435 (alpha-Fluoro-beta-ureidopropionic acid)

HEADER    PROTEIN                                 12-MAR-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-MAR-19         0                                  
HETATM    1  O   UNK     0      26.690 -25.342   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      28.024 -24.572   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      29.358 -25.342   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      30.692 -24.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.025 -25.342   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.359 -24.572   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      34.693 -25.342   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      33.359 -23.033   0.000  0.00  0.00           O+0
HETATM    9  F   UNK     0      32.025 -26.882   0.000  0.00  0.00           F+0
HETATM   10  N   UNK     0      28.024 -23.032   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5                                                            
CONECT   10    2                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0060435 (alpha-Fluoro-beta-ureidopropionic acid)

COMPND    HMDB0060435
HETATM    1  N1  UNL     1       2.543   1.384   0.228  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.320   0.147   0.505  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.401  -0.728   0.382  1.00  0.00           O  
HETATM    4  N2  UNL     1       1.032  -0.263   0.910  1.00  0.00           N  
HETATM    5  C2  UNL     1      -0.111   0.022   0.080  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.374  -0.516   0.723  1.00  0.00           C  
HETATM    7  F1  UNL     1      -1.214  -1.873   0.861  1.00  0.00           F  
HETATM    8  C4  UNL     1      -2.579  -0.205  -0.042  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.314  -1.117  -0.488  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.961   1.099  -0.306  1.00  0.00           O  
HETATM   11  H1  UNL     1       1.787   2.066   0.302  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.414  -1.633   0.841  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.904  -0.763   1.790  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.071  -0.477  -0.899  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.173   1.111  -0.119  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.443  -0.090   1.742  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.303   1.838  -0.222  1.00  0.00           H  
CONECT    1    2    2   11
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13
CONECT    5    6   14   15
CONECT    6    7    8   16
CONECT    8    9    9   10
CONECT   10   17
END
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SMILES for HMDB0060435 (alpha-Fluoro-beta-ureidopropionic acid)

NC(=O)NCC(F)C(O)=O
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INCHI for HMDB0060435 (alpha-Fluoro-beta-ureidopropionic acid)

InChI=1S/C4H7FN2O3/c5-2(3(8)9)1-7-4(6)10/h2H,1H2,(H,8,9)(H3,6,7,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Fluoro-3-ureidopropionic acidKegg
2-Fluoro-3-ureidopropionateGenerator
a-Fluoro-b-ureidopropionateGenerator
a-Fluoro-b-ureidopropionic acidGenerator
alpha-Fluoro-beta-ureidopropionateGenerator
Α-fluoro-β-ureidopropionateGenerator
Α-fluoro-β-ureidopropionic acidGenerator
FUPAHMDB
2-Fluoro-3-[(C-hydroxycarbonimidoyl)amino]propanoateGenerator
Chemical FormulaC4H7FN2O3
Average Molecular Weight150.1084
Monoisotopic Molecular Weight150.044070305
IUPAC Name3-(carbamoylamino)-2-fluoropropanoic acid
Traditional Name3-(carbamoylamino)-2-fluoropropanoic acid
CAS Registry NumberNot Available
SMILES
NC(=O)NCC(F)C(O)=O
InChI Identifier
InChI=1S/C4H7FN2O3/c5-2(3(8)9)1-7-4(6)10/h2H,1H2,(H,8,9)(H3,6,7,10)
InChI KeyFKTHAKABFGARQH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAlpha-halocarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Carbonic acid derivative
  • Urea
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Alkyl halide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 LocationsNot Available
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 IDC16631
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151244
PDB IDNot Available
ChEBI ID80625
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 References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details
1. Dihydropyrimidinase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the second step of the reductive pyrimidine degradation, the reversible hydrolytic ring opening of dihydropyrimidines. Can catalyze the ring opening of 5,6-dihydrouracil to N-carbamyl-alanine and of 5,6-dihydrothymine to N-carbamyl-amino isobutyrate.
Gene Name:
DPYS
Uniprot ID:
Q14117
Molecular weight:
56629.36
Reactions
5,6-Dihydro-5-fluorouracil + Water → alpha-Fluoro-beta-ureidopropionic aciddetails
Enzyme Details
2. Beta-ureidopropionase
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
Specific function:
Converts N-carbamyl-beta-aminoisobutyric acid and N-carbamyl-beta-alanine to, respectively, beta-aminoisobutyric acid and beta-alanine, ammonia and carbon dioxide.
Gene Name:
UPB1
Uniprot ID:
Q9UBR1
Molecular weight:
43165.705
Reactions
alpha-Fluoro-beta-ureidopropionic acid + Water → alpha-Fluoro-beta-alanine + Carbon dioxide + Ammoniadetails