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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:09:02 UTC
Update Date2019-07-23 07:15:27 UTC
HMDB IDHMDB0060949
Secondary Accession Numbers
  • HMDB60949
Metabolite Identification
Common Name2-hydroxyflutamide
Description2-hydroxyflutamide, also known as OH-flutamide, belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups. Antiandrogens alter the androgen pathway by blocking the appropriate receptors, competing for binding sites on the cell's surface, or affecting androgen production. Environmental antiandrogens can have harmful effects on reproductive organ development in fetuses exposed in utero as well as their offspring. 2-hydroxyflutamide is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-hydroxyflutamide is a potentially toxic compound. It competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. Flutamide is an oral nonsteroidal antiandrogen drug primarily used to treat prostate cancer. 2-hydroxyflutamide is a metabolite of flutamide. Steroidal antiandrogens not only counter androgens, but also affect secondary sex characteristics.
Structure
Data?1563866127
Synonyms
ValueSource
OH-FlutamideHMDB
Chemical FormulaC11H11F3N2O4
Average Molecular Weight292.2112
Monoisotopic Molecular Weight292.067091465
IUPAC Name2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanimidic acid
Traditional Namehydroxyflutamide
CAS Registry NumberNot Available
SMILES
CC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F
InChI Identifier
InChI=1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)
InChI KeyYPQLFJODEKMJEF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassTrifluoromethylbenzenes
Direct ParentTrifluoromethylbenzenes
Alternative Parents
Substituents
  • Trifluoromethylbenzene
  • Nitrobenzene
  • Anilide
  • Nitroaromatic compound
  • N-arylamide
  • Tertiary alcohol
  • Carboxamide group
  • C-nitro compound
  • Secondary carboxylic acid amide
  • Organic nitro compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Alkyl halide
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organic oxygen compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Alkyl fluoride
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic zwitterion
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
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
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP1.91ALOGPS
logP2.94ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)0.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.64 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.88 m³·mol⁻¹ChemAxon
Polarizability24.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+162.91130932474
DeepCCS[M-H]-160.55330932474
DeepCCS[M-2H]-194.42230932474
DeepCCS[M+Na]+169.81630932474
AllCCS[M+H]+160.332859911
AllCCS[M+H-H2O]+157.132859911
AllCCS[M+NH4]+163.432859911
AllCCS[M+Na]+164.332859911
AllCCS[M-H]-158.832859911
AllCCS[M+Na-2H]-158.532859911
AllCCS[M+HCOO]-158.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-hydroxyflutamideCC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F2289.0Standard polar33892256
2-hydroxyflutamideCC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F1979.8Standard non polar33892256
2-hydroxyflutamideCC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F1924.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-hydroxyflutamide,1TMS,isomer #1CC(C)(O[Si](C)(C)C)C(O)=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C11812.1Semi standard non polar33892256
2-hydroxyflutamide,1TMS,isomer #2CC(C)(O)C(=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)O[Si](C)(C)C1740.4Semi standard non polar33892256
2-hydroxyflutamide,2TMS,isomer #1CC(C)(O[Si](C)(C)C)C(=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)O[Si](C)(C)C1797.9Semi standard non polar33892256
2-hydroxyflutamide,1TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)C(O)=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C12073.4Semi standard non polar33892256
2-hydroxyflutamide,1TBDMS,isomer #2CC(C)(O)C(=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)O[Si](C)(C)C(C)(C)C1994.9Semi standard non polar33892256
2-hydroxyflutamide,2TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)C(=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)O[Si](C)(C)C(C)(C)C2289.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxyflutamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9050000000-f84e588ae9034a41b2dc2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxyflutamide GC-MS (2 TMS) - 70eV, Positivesplash10-0089-9611200000-62d9053b443fcb3656422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-hydroxyflutamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-hydroxyflutamide 90V, Negative-QTOFsplash10-06g0-9800000000-18021dcb8f1e955f52ad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-hydroxyflutamide 75V, Negative-QTOFsplash10-0a6r-6940000000-dd38c2394309e1626e1e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-hydroxyflutamide 75V, Positive-QTOFsplash10-0a6r-6940000000-81afeee01eada15bcf382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-hydroxyflutamide 60V, Negative-QTOFsplash10-0a4i-2490000000-6d0e498f9c29ac103dd72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-hydroxyflutamide 15V, Negative-QTOFsplash10-0006-0090000000-1892a491307294bb679e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-hydroxyflutamide 30V, Negative-QTOFsplash10-0a4i-0090000000-73482035831e8bedb25c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-hydroxyflutamide 45V, Negative-QTOFsplash10-0a4i-0090000000-e7bc28de00b2591fa92a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyflutamide 10V, Positive-QTOFsplash10-0006-0090000000-4c17b53efb57846397e42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyflutamide 20V, Positive-QTOFsplash10-00kr-3090000000-d9e96ed3ee61c4eaf8ed2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyflutamide 40V, Positive-QTOFsplash10-059f-9010000000-67e035c44d2e533ec7302016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyflutamide 10V, Negative-QTOFsplash10-0006-0090000000-c848958ccc3b75da2ac32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyflutamide 20V, Negative-QTOFsplash10-0006-1190000000-78cf87749f2c226b1da42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-hydroxyflutamide 40V, Negative-QTOFsplash10-0k9i-9200000000-b8932182dc70103690522016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDC14204
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydroxyflutamide
METLIN IDNot Available
PubChem Compound91649
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