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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:47 UTC
HMDB IDHMDB0014931
Secondary Accession Numbers
  • HMDB14931
Metabolite Identification
Common NameHaloprogin
DescriptionHaloprogin is used as a topical ointment or cream in the treatment of Tinea infections. Tinea infections are superficial fungal infections caused by three species of fungi collectively known as dermatophytes (Trichophyton, Microsporum and Epidermophyton). Commonly these infections are named for the body part affected, including tinea corporis (general skin), tinea cruris (groin), and tinea pedis (feet). Haloprogin is a halogenated phenolic ether administered topically for dermotaphytic infections. The mechanism of action is unknown, but it is thought to be via inhibition of oxygen uptake and disruption of yeast membrane structure and function.
Structure
Data?1582753236
Synonyms
ValueSource
HalotexKegg
Théraplix brand OF haloproginHMDB
MycilanHMDB
Westwood squibb brand OF haloproginHMDB
3-Iodo-2-propynyl 2,4,5-trichlorophenyl etherHMDB
Chemical FormulaC9H4Cl3IO
Average Molecular Weight361.391
Monoisotopic Molecular Weight359.837241291
IUPAC Name1,2,4-trichloro-5-[(3-iodoprop-2-yn-1-yl)oxy]benzene
Traditional Namehaloprogin
CAS Registry Number777-11-7
SMILES
ClC1=CC(Cl)=C(Cl)C=C1OCC#CI
InChI Identifier
InChI=1S/C9H4Cl3IO/c10-6-4-8(12)9(5-7(6)11)14-3-1-2-13/h4-5H,3H2
InChI KeyCTETYYAZBPJBHE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Ether
  • Haloacetylene or derivatives
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organochloride
  • Organoiodide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point113.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.006 g/LNot Available
LogP5.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.006 g/LALOGPS
logP4.69ALOGPS
logP4.85ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity66.88 m³·mol⁻¹ChemAxon
Polarizability26.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+148.07330932474
DeepCCS[M-H]-145.71530932474
DeepCCS[M-2H]-180.02730932474
DeepCCS[M+Na]+154.75630932474
AllCCS[M+H]+160.532859911
AllCCS[M+H-H2O]+157.432859911
AllCCS[M+NH4]+163.432859911
AllCCS[M+Na]+164.332859911
AllCCS[M-H]-137.632859911
AllCCS[M+Na-2H]-138.132859911
AllCCS[M+HCOO]-138.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HaloproginClC1=CC(Cl)=C(Cl)C=C1OCC#CI2686.6Standard polar33892256
HaloproginClC1=CC(Cl)=C(Cl)C=C1OCC#CI2087.8Standard non polar33892256
HaloproginClC1=CC(Cl)=C(Cl)C=C1OCC#CI2052.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Haloprogin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nvi-2937000000-e0fbc50dec2df8a7392c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Haloprogin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 10V, Positive-QTOFsplash10-03di-0009000000-205241bf6f19269ac44f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 20V, Positive-QTOFsplash10-03di-0009000000-685736b870ca3a5b73962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 40V, Positive-QTOFsplash10-01q9-0904000000-0fa7f51cc65c247bc53e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 10V, Negative-QTOFsplash10-0a4i-0009000000-613da8314566eab0ea092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 20V, Negative-QTOFsplash10-0a4i-0009000000-5526c9d6e567956ca1c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 40V, Negative-QTOFsplash10-0a6r-0639000000-48169dabf0e58c7b946c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 10V, Positive-QTOFsplash10-03di-0009000000-13123a05c84264f3a2632021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 20V, Positive-QTOFsplash10-03di-0029000000-82363b16547174d037832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 40V, Positive-QTOFsplash10-06w9-4296000000-43a5c95da82f2b8363042021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 10V, Negative-QTOFsplash10-0a4i-0009000000-c2d55deaed82c6582a922021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 20V, Negative-QTOFsplash10-0a4i-0009000000-c2d55deaed82c6582a922021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Haloprogin 40V, Negative-QTOFsplash10-0a4i-2249000000-3d6d4d91ac564a883d2b2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00793 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00793 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00793
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3440
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHaloprogin
METLIN IDNot Available
PubChem Compound3561
PDB IDNot Available
ChEBI ID353862
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 References
  1. Harrison EF, Zygmunt WA: Haloprogin: mode of action studies in Candida albicans. Can J Microbiol. 1974 Sep;20(9):1241-5. [PubMed:4608935 ]
  2. Harrison EF, Zwadyk P Jr, Bequette RJ, Hamlow EE, Tavormina PA, Zygmunt WA: Haloprogin: a topical antifungal agent. Appl Microbiol. 1970 May;19(5):746-50. [PubMed:5422306 ]