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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 10:07:05 UTC
Update Date2021-09-26 23:04:43 UTC
HMDB IDHMDB0252262
Secondary Accession NumbersNone
Metabolite Identification
Common NameFingolimod
DescriptionFingolimod, also known as FTY720 or gilenya, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Fingolimod is a very strong basic compound (based on its pKa). Fingolimod-phosphate blocks the capacity of lymphocytes to egress from lymph nodes, reducing the number of lymphocytes in peripheral blood. Risk of infections. Immunologic responses were further decreased with fingolimod 1.25 mg (a dose higher than recommended for MS). Compared to placebo, antigen-specific IgM titers were decreased by 91% and 25% in response to KLH and PPV, respectively. -oxidative biotransformation mainly via the cytochrome P450 4F2 isoenzyme and subsequent fatty acid-like degradation to inactive metabolites. Potential to prolong the QT interval. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fingolimod is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fingolimod is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
FingolimodumChEBI
FTY720ChEBI
GilenyaKegg
2-amino-2-(2-(4-Octylphenyl)ethyl)-1,3-propanediol hydrochlorideMeSH
Fingolimod hydrochlorideMeSH
FTY-720MeSH
GileniaMeSH
FTY 720MeSH
Hydrochloride, fingolimodMeSH
Chemical FormulaC19H33NO2
Average Molecular Weight307.4708
Monoisotopic Molecular Weight307.251129305
IUPAC Name2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol
Traditional Namefingolimod
CAS Registry NumberNot Available
SMILES
CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1
InChI Identifier
InChI=1S/C19H33NO2/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-22/h9-12,21-22H,2-8,13-16,20H2,1H3
InChI KeyKKGQTZUTZRNORY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4ALOGPS
logP4.06ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.41ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity93.28 m³·mol⁻¹ChemAxon
Polarizability38.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+183.16430932474
DeepCCS[M-H]-180.80630932474
DeepCCS[M-2H]-213.69230932474
DeepCCS[M+Na]+189.32630932474
AllCCS[M+H]+181.132859911
AllCCS[M+H-H2O]+178.132859911
AllCCS[M+NH4]+183.832859911
AllCCS[M+Na]+184.632859911
AllCCS[M-H]-183.232859911
AllCCS[M+Na-2H]-184.532859911
AllCCS[M+HCOO]-186.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FingolimodCCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C13311.3Standard polar33892256
FingolimodCCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C12599.9Standard non polar33892256
FingolimodCCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C12609.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fingolimod,3TMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C)(CO[Si](C)(C)C)N[Si](C)(C)C)C=C12634.0Semi standard non polar33892256
Fingolimod,3TMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C)(CO[Si](C)(C)C)N[Si](C)(C)C)C=C12680.4Standard non polar33892256
Fingolimod,3TMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C)(CO[Si](C)(C)C)N[Si](C)(C)C)C=C12724.2Standard polar33892256
Fingolimod,3TMS,isomer #2CCCCCCCCC1=CC=C(CCC(CO)(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C12847.5Semi standard non polar33892256
Fingolimod,3TMS,isomer #2CCCCCCCCC1=CC=C(CCC(CO)(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C12740.2Standard non polar33892256
Fingolimod,3TMS,isomer #2CCCCCCCCC1=CC=C(CCC(CO)(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C12896.3Standard polar33892256
Fingolimod,4TMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C)(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C12889.2Semi standard non polar33892256
Fingolimod,4TMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C)(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C12780.2Standard non polar33892256
Fingolimod,4TMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C)(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C12708.5Standard polar33892256
Fingolimod,3TBDMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C13380.4Semi standard non polar33892256
Fingolimod,3TBDMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C13218.7Standard non polar33892256
Fingolimod,3TBDMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C13015.0Standard polar33892256
Fingolimod,3TBDMS,isomer #2CCCCCCCCC1=CC=C(CCC(CO)(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13538.6Semi standard non polar33892256
Fingolimod,3TBDMS,isomer #2CCCCCCCCC1=CC=C(CCC(CO)(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13264.3Standard non polar33892256
Fingolimod,3TBDMS,isomer #2CCCCCCCCC1=CC=C(CCC(CO)(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13097.7Standard polar33892256
Fingolimod,4TBDMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13760.1Semi standard non polar33892256
Fingolimod,4TBDMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13439.8Standard non polar33892256
Fingolimod,4TBDMS,isomer #1CCCCCCCCC1=CC=C(CCC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13023.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9150000000-3d6345487f899f4e1abf2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fingolimod GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 10V, Positive-QTOFsplash10-0a4l-2196000000-fcd0d97799da27c553032017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 20V, Positive-QTOFsplash10-0ukc-4190000000-b1b26fb51c05d0f1f5192017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 40V, Positive-QTOFsplash10-052f-9400000000-98a9c83ab83597c9b41a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 10V, Negative-QTOFsplash10-0a4i-0039000000-8a84119f49496a6e3fe02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 20V, Negative-QTOFsplash10-0a4r-1092000000-3f154d83e4526c400d8b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 40V, Negative-QTOFsplash10-0a4i-9060000000-81a2e903ffabaa3956392017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 10V, Positive-QTOFsplash10-0a4i-0089000000-5722c3832b418bc6a3a32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 20V, Positive-QTOFsplash10-08mi-3290000000-f5d07db2b1e34e6f74d82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 40V, Positive-QTOFsplash10-0api-9500000000-91433d3279fae2af3db82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 10V, Negative-QTOFsplash10-0a4i-0009000000-bda0c91e6f0fce2c2b1e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 20V, Negative-QTOFsplash10-0a4i-0069000000-f5344e48febd463c62db2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fingolimod 40V, Negative-QTOFsplash10-0apj-0590000000-34769ab42847fc0a49872021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08868
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFingolimod
METLIN IDNot Available
PubChem Compound107970
PDB IDNot Available
ChEBI ID63115
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]