Miltefosine (CHEM018656)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:25:25 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018656
Identification
Common NameMiltefosine
ClassSmall Molecule
DescriptionA phospholipid that is the hexadecyl monoester of phosphocholine.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HexadecylphosphocholineChEBI
HexadecylphosphorylcholineChEBI
MiltefosinaChEBI
MiltefosinumChEBI
MonohexadecylphosphocholineChEBI
MonohexadecylphosphorylcholineChEBI
ImpavidoKegg
HDPCMeSH
MiltexMeSH
N-HexadecylphosphorylcholineMeSH
Chemical FormulaC21H46NO4P
Average Molecular Mass407.576 g/mol
Monoisotopic Mass407.316 g/mol
CAS Registry Number58066-85-6
IUPAC Namehexadecyl 2-(trimethylazaniumyl)ethyl phosphate
Traditional Namemiltex
SMILESCCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C
InChI IdentifierInChI=1S/C21H46NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-25-27(23,24)26-21-19-22(2,3)4/h5-21H2,1-4H3
InChI KeyPQLXHQMOHUQAKB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentPhosphocholines
Alternative Parents
Substituents
  • Phosphocholine
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Tetraalkylammonium salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 Solubility0.00022 g/LALOGPS
logP2.68ALOGPS
logP2.25ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.59 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity125.51 m³·mol⁻¹ChemAxon
Polarizability50.58 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-9432000000-642b57f37f036f7f50c3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0550-9061400000-e095141ca899b073c533Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-5690000000-7d225d53e68dce85d25bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9410000000-f258e2588380399fafa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0003900000-1691b838c8f926e3c434Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kor-2019200000-4631320f9dcefaac10a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9011000000-f7696a7826d1d702049dSpectrum
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 IDDB09031
HMDB IDHMDB0254735
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMiltefosine
Chemspider ID3473
ChEBI ID75283
PubChem Compound ID3599
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22385017
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22935677
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22995097
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23136856
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23165465
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23199340
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23239091
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23243111
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23434530
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23434716
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23468121
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23601234
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23673723
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23723490
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23729024
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23738749
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23740007
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23811261
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23811637
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23861311
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23871798
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23890327
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23930349