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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:26 UTC
Update Date2019-07-23 06:09:30 UTC
HMDB IDHMDB0031784
Secondary Accession Numbers
  • HMDB31784
Metabolite Identification
Common NameHalofuginone
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
Structure
Data?1563862170
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 Weight414.681
Monoisotopic Molecular Weight413.014181779
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
CAS Registry Number55837-20-2
SMILES
OC1CCCNC1CC(=O)CN1C=NC2=C(C=C(Cl)C(Br)=C2)C1=O
InChI Identifier
InChI=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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

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 Solubility0.11 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FooDB IDFDB008457
KNApSAcK IDNot Available
Chemspider ID56619
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHalofuginone
METLIN IDNot Available
PubChem Compound62894
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:19390970 ]
  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. [PubMed:20000346 ]
  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. [PubMed:9407501 ]
  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. [PubMed:11099465 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in extracellular matrix structural constituent
Specific function:
Type I collagen is a member of group I collagen (fibrillar forming collagen)
Gene Name:
COL1A1
Uniprot ID:
P02452
Molecular weight:
138941.1
References
  1. 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. [PubMed:11099465 ]
General function:
Involved in metalloendopeptidase activity
Specific function:
PEX, the C-terminal non-catalytic fragment of MMP2, posseses anti-angiogenic and anti-tumor properties and inhibits cell migration and cell adhesion to FGF2 and vitronectin. Ligand for integrinv/beta3 on the surface of blood vessels
Gene Name:
MMP2
Uniprot ID:
P08253
Molecular weight:
73881.7
References
  1. 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. [PubMed:11099465 ]