You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:09:30 UTC
Update Date2017-12-07 04:18:22 UTC
HMDB IDHMDB0040599
Secondary Accession Numbers
  • HMDB40599
Metabolite Identification
Common Name(±)-Fenarimol
DescriptionFenarimol, also known as rubigan-4 or rubigan 12 rc, is a member of the class of compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Fenarimol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Within the cell, fenarimol is primarily located in the membrane (predicted from logP). Fenarimol is a non-carcinogenic (not listed by IARC) potentially toxic compound. Fenarimol, sold under the tradenames Bloc, Rimidin and Rubigan, is a fungicide which acts against rusts, blackspot and mildew fungi. It is used on ornamental plants, trees, lawns, tomatoes, peppers, eggplants, cucumbers and melons. It is mainly used to control powdery mildew. It works by inhibiting the fungus's biosynthesis of important steroid molecules (Wikipedia). Fenarimol is an antiandrogen. It has effects on the reproductive organs and prostate gene expression levels. Studies suggested that the adverse effects of Fenarimol in males are mediated at least partialy via antagonism or androgen receptor (T3DB) (±)-Fenarimol is an Agricultural and horticultural fungicide..
Structure
Thumb
Synonyms
ValueSource
Rubigan-4MeSH
alpha-(2-Chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanolMeSH
Rubigan 12 RCMeSH
Chemical FormulaC17H12Cl2N2O
Average Molecular Weight331.196
Monoisotopic Molecular Weight330.03266843
IUPAC Name(2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol
Traditional NameBLOC
CAS Registry NumberNot Available
SMILES
OC(C1=CC=C(Cl)C=C1)(C1=CN=CN=C1)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C17H12Cl2N2O/c18-14-7-5-12(6-8-14)17(22,13-9-20-11-21-10-13)15-3-1-2-4-16(15)19/h1-11,22H
InChI KeyNHOWDZOIZKMVAI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Pyrimidine
  • Heteroaromatic compound
  • Tertiary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Origin
  • Food
  • Toxin/Pollutant
Biofunction
  • Nutrient
Application
  • Agricultural Chemical
Cellular locations
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point117 - 119 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
logP3.13ALOGPS
logP3.92ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)12.13ChemAxon
pKa (Strongest Basic)1.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.01 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity89.59 m³·mol⁻¹ChemAxon
Polarizability32.33 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, Positivesplash10-05n0-8961000000-075004d353317fe01459View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02fx-7097000000-54327afd3e0035057093View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0059000000-e16b8557415e91c4d761View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0179000000-d173b174711110be6e3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-1590000000-b860e5d396c463966a3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-59be4acc257da6550208View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2439000000-094c180523b4bfe77279View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-4953000000-69bcd9deed0b45d98ca2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0ktr-3930000000-e1ca6756e783ae9bdd9cView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDFDB020386
KNApSAcK IDNot Available
Chemspider ID39394
KEGG Compound IDC11226
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenarimol
METLIN IDNot Available
PubChem Compound43226
PDB IDNot Available
ChEBI ID83686
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .