Halofuginone (CHEM026654)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:09:01 UTC
Update Date2016-11-09 01:18:18 UTC
Accession NumberCHEM026654
Identification
Common NameHalofuginone
ClassSmall Molecule
DescriptionVeterinary antiprotozoal agent. Poultry feed additive for prevention of coccidiosis. Halofuginone is a coccidiostat used in veterinary medicine. It is derived from dichrorine, a kind of alkaloids which can be found in the Chinese herb Chang Shan (Dichroa febrifuga). Halofuginone, a fully synthetic small molecule, is a potent and selective regulator of stromal cell activation, cell migration and Collagen type I synthesis, a process that has been identified as a 'master switch' in the body's tissue repair process
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone, 9ciHMDB
C16H17BRCLN3O3HMDB
HalofuginonaHMDB
HalofuginonumHMDB
7-Bromo-6-chlorofebrifugineHMDB
StenorolHMDB
HalofunginoneHMDB
HalofuginoneMeSH
Chemical FormulaC16H17BrClN3O3
Average Molecular Mass414.681 g/mol
Monoisotopic Mass413.014 g/mol
CAS Registry Number55837-20-2
IUPAC Name7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one
Traditional Name7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]quinazolin-4-one
SMILESOC1CCCNC1CC(=O)CN1C=NC2=C(C=C(Cl)C(Br)=C2)C1=O
InChI IdentifierInChI=1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2
InChI KeyLVASCWIMLIKXLA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolines
Alternative Parents
Substituents
  • Quinazoline
  • Pyrimidone
  • Aryl bromide
  • Aryl chloride
  • Aryl halide
  • Beta-aminoketone
  • Benzenoid
  • Pyrimidine
  • Piperidine
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Ketone
  • Lactam
  • Secondary alcohol
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organobromide
  • Organohalogen compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP1.38ALOGPS
logP1.71ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.48ChemAxon
pKa (Strongest Basic)9.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.87 m³·mol⁻¹ChemAxon
Polarizability36.21 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9531000000-ad6d23d97b7b8b802456Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9772100000-33f767c26405baf989d5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0019400000-ef37bff5ad2e7944f658Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-4229100000-9dcac476806bf59275f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-2091000000-5bf157bd94019fecfb6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0023900000-140a33008401d0012984Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-5095200000-5d19f101c04a8000ea81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-1190000000-45f00a76c454d6ef5d31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009300000-7afba3c2c7d0c13e0159Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022a-0149300000-66b7f003bd06aa717823Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ea-5093000000-0c47978e630a5c91d73eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-0046900000-b271a5f6055f2a12bc42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0139000000-08906f28b7da88fd8c64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2190100000-7cf63cdf29574b0ee2a0Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031784
FooDB IDFDB008457
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHalofuginone
Chemspider ID56619
ChEBI IDNot Available
PubChem Compound ID62894
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Karakoyun B, Yuksel M, Ercan F, Salva E, Isik I, Yegen BC: Halofuginone, a specific inhibitor of collagen type 1 synthesis, ameliorates oxidant colonic damage in rats with experimental colitis. Dig Dis Sci. 2010 Mar;55(3):607-16. doi: 10.1007/s10620-009-0798-0. Epub 2009 Apr 24.
2. McLaughlin NP, Evans P: Dihydroxylation of vinyl sulfones: stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone. J Org Chem. 2010 Jan 15;75(2):518-21. doi: 10.1021/jo902396m.
3. Nagler A, Katz A, Aingorn H, Miao HQ, Condiotti R, Genina O, Pines M, Vlodavsky I: Inhibition of glomerular mesangial cell proliferation and extracellular matrix deposition by halofuginone. Kidney Int. 1997 Dec;52(6):1561-9.
4. Elkin M, Miao HQ, Nagler A, Aingorn E, Reich R, Hemo I, Dou HL, Pines M, Vlodavsky I: Halofuginone: a potent inhibitor of critical steps in angiogenesis progression. FASEB J. 2000 Dec;14(15):2477-85.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.