Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:45:29 UTC
HMDB IDHMDB0015175
Secondary Accession Numbers
  • HMDB15175
Metabolite Identification
Common NameThalidomide
DescriptionA piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppresive and anti-angiogenic activity. It inhibits release of tumor necrosis factor-alpha from monocytes, and modulates other cytokine action. [PubChem]
Structure
Data?1582753267
Synonyms
ValueSource
ThalomidKegg
ThaledKegg
alpha-PhthalimidoglutarimideHMDB
N-Phthalimidoglutamic acid imideHMDB
N-PhthaloylglutamimideHMDB
N-Phthalylglutamic acid imideHMDB
Thalidomine usp26HMDB
SedovalHMDB
Celgene brand OF thalidomideHMDB
ThalidomideMeSH
Chemical FormulaC13H10N2O4
Average Molecular Weight258.2295
Monoisotopic Molecular Weight258.064056818
IUPAC Name2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
Traditional Namethalidomide
CAS Registry Number50-35-1
SMILES
O=C1N(C2CCC(=O)NC2=O)C(=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
InChI KeyUEJJHQNACJXSKW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindolines
Direct ParentPhthalimides
Alternative Parents
Substituents
  • Phthalimide
  • Alpha-amino acid or derivatives
  • Isoindole
  • Piperidinedione
  • Delta-lactam
  • Piperidinone
  • Benzenoid
  • Piperidine
  • Carboxylic acid imide, n-substituted
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.55 g/LNot Available
LogP0.3Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.55 g/LALOGPS
logP10(0.42) g/LALOGPS
logP10(0.016) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)11.59ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.32 m³·mol⁻¹ChemAxon
Polarizability24.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.00131661259
DarkChem[M-H]-158.38631661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thalidomide GC-MS (Non-derivatized) - 70eV, Positivesplash10-05d0-4950000000-f29254c7cc48a749c1002017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thalidomide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thalidomide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thalidomide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0wba-4900000000-77362eaf27267f59650d2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide LC-ESI-qTof , Positive-QTOFsplash10-000i-1940000000-f6d6997d1eaa7a83ec1b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide LC-ESI-qTof , Positive-QTOFsplash10-000i-0930000000-e92e8e23d5db87f50f532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide LC-ESI-qTof , Positive-QTOFsplash10-0019-2900000000-ecfd1b7ec17b857ea9772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide , positive-QTOFsplash10-000i-0930000000-e92e8e23d5db87f50f532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide , positive-QTOFsplash10-000i-1940000000-f6d6997d1eaa7a83ec1b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide , positive-QTOFsplash10-0019-2900000000-ecfd1b7ec17b857ea9772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 60V, Positive-QTOFsplash10-0aou-3910000000-91636cf8948ff2a1ec8c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 75V, Negative-QTOFsplash10-0aou-4900000000-0354536dffa9acdee12d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 90V, Negative-QTOFsplash10-066u-6900000000-ea3e7b4b381e65a7c9a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 75V, Positive-QTOFsplash10-0aou-4900000000-c5062441ebfb6523331b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 45V, Negative-QTOFsplash10-0bvl-2970000000-1e251d07e623c9fbe2a22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 60V, Negative-QTOFsplash10-0aou-3910000000-19940b0b041ba51e96e02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 30V, Negative-QTOFsplash10-0a6r-0190000000-a818a5ae6100d0f996ba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 15V, Negative-QTOFsplash10-0a4i-0090000000-42e8be928c8508c213f22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thalidomide 45V, Positive-QTOFsplash10-0bvl-2970000000-fcf57e68d7f7156f09d42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 10V, Positive-QTOFsplash10-0a4i-0090000000-094c39302b7589d692932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 20V, Positive-QTOFsplash10-0a4r-0590000000-a8eb9abb005e68bb1fdf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 40V, Positive-QTOFsplash10-000f-9800000000-e219527727ba0e4f62dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 10V, Negative-QTOFsplash10-0a4i-0190000000-88a6f8cb2bfe0f1b603f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 20V, Negative-QTOFsplash10-0bti-1790000000-bdf020cb11e65e0077f72016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 40V, Negative-QTOFsplash10-01oy-9700000000-ce19845489ffe3fdb3892016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 10V, Negative-QTOFsplash10-0bta-0960000000-38a7ecf36472375bfe142021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 20V, Negative-QTOFsplash10-0a4j-1590000000-40230dba1a083dee9f102021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 40V, Negative-QTOFsplash10-0005-4900000000-b49c37804603e0525f052021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thalidomide 10V, Positive-QTOFsplash10-052b-0960000000-d36ac6ec3b1b89dff27d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01041 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01041 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01041
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5233
KEGG Compound IDC07910
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThalidomide
METLIN IDNot Available
PubChem Compound5426
PDB IDNot Available
ChEBI ID74947
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1215651
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available