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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:53:26 UTC
Update Date2017-12-07 04:30:12 UTC
HMDB IDHMDB0042019
Secondary Accession Numbers
  • HMDB42019
Metabolite Identification
Common NameSuxibuzone
DescriptionSuxibuzone, also known as calibene or danilon, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Suxibuzone is considered to be a practically insoluble (in water) and relatively neutral molecule. Suxibuzone has been primarily detected in urine. Within the cell, suxibuzone is primarily located in the membrane (predicted from logP) and cytoplasm.
Structure
Thumb
Synonyms
ValueSource
4-Butyl-4-hydroxymethyl-1,2-diphenyl-3,5-pyrazolidinedione hydrogen succinateChEBI
4-Hydroxymethylbutazolidine hemisuccinateChEBI
SuxibuzonaChEBI
SuxibuzonumChEBI
4-Butyl-4-hydroxymethyl-1,2-diphenyl-3,5-pyrazolidinedione hydrogen succinic acidGenerator
4-Hydroxymethylbutazolidine hemisuccinic acidGenerator
4-[(4-Butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy]-4-oxobutanoic acidHMDB
CalibeneHMDB
DanilonHMDB
FlogosHMDB
SolurolHMDB
1,2-Diphenyl-4-N-butyl-4-hydroxymethyl-3,5-dioxopyrazolidine hemisuccinateMeSH
4-Butyl-4-(beta-carboxypropionyloxymethyl)-1,2-diphenyl-3,5-pyrazolidinedioneMeSH
Chemical FormulaC24H26N2O6
Average Molecular Weight438.473
Monoisotopic Molecular Weight438.179086574
IUPAC Name4-[(4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy]-4-oxobutanoic acid
Traditional Nameflogos
CAS Registry Number27470-51-5
SMILES
CCCCC1(COC(=O)CCC(O)=O)C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C24H26N2O6/c1-2-3-16-24(17-32-21(29)15-14-20(27)28)22(30)25(18-10-6-4-7-11-18)26(23(24)31)19-12-8-5-9-13-19/h4-13H,2-3,14-17H2,1H3,(H,27,28)
InChI KeyONWXNHPOAGOMTG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Pyrazolidinone
  • Benzenoid
  • Pyrazolidine
  • Carboxylic acid ester
  • Carboxylic acid hydrazide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP2.54ALOGPS
logP3.68ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area104.22 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity115.08 m³·mol⁻¹ChemAxon
Polarizability45.51 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9102000000-05271e9cb1c69a093216View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0092-9512200000-652d65232c7b44f432b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-2109800000-8d6f7d30a588fa401d12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-5119100000-8bcaaed58834a2a709daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9343000000-87bbcc8240cad42da3dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4s-4109400000-0190bb998c8bbe904ae8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9418200000-d9b04cea4a9a7e5ff37cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-9610000000-a170faed9708aa3e31e7View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5169
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSuxibuzone
METLIN IDNot Available
PubChem Compound5362
PDB IDNot Available
ChEBI ID32173
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yasuda Y, Shindo T, Mitani N, Ishida N, Oono F, Kageyama T: Comparison of the absorption, excretion, and metabolism of suxibuzone and phenylbutazone in humans. J Pharm Sci. 1982 May;71(5):565-72. [PubMed:7097505 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Mizushima Y, Shiokawa Y, Honma M, Kageyama T: A double-blind comparison of phenylbutazone and suxibuzone, a prodrug of phenylbutazone, in rheumatoid arthritis. Int J Tissue React. 1983;5(1):35-9. [PubMed:6345427 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.