Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-06-05 01:09:24 UTC
Update Date2019-07-23 07:14:31 UTC
HMDB IDHMDB0060524
Secondary Accession Numbers
  • HMDB60524
Metabolite Identification
Common Name3-Iodothyronamine
Description3-Iodothyronamine, also known as T(1)am CPD, belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. 3-Iodothyronamine is a very strong basic compound (based on its pKa). T1AM is the most potent TAAR1 agonist yet discovered. T1AM is a high-affinity ligand for the trace amine-associated receptor TAAR1, a recently discovered G protein-coupled receptor. 3-Iodothyronamine is an endogenous thyronamine.
Structure
Data?1563866071
Synonyms
ValueSource
T(1)AM CPDHMDB
Chemical FormulaC14H14INO2
Average Molecular Weight355.1709
Monoisotopic Molecular Weight355.006922117
IUPAC Name4-[4-(2-aminoethyl)-2-iodophenoxy]phenol
Traditional Name3-iodothyronamine
CAS Registry NumberNot Available
SMILES
NCCC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C14H14INO2/c15-13-9-10(7-8-16)1-6-14(13)18-12-4-2-11(17)3-5-12/h1-6,9,17H,7-8,16H2
InChI KeyXIINYOJWNGOUPF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • Diaryl ether
  • Phenethylamine
  • 2-arylethylamine
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Ether
  • Organic oxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Amine
  • Primary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
Water Solubility0.032 g/LALOGPS
logP3.74ALOGPS
logP2.88ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)10.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity80.87 m³·mol⁻¹ChemAxon
Polarizability30.39 ųChemAxon
Number of Rings2ChemAxon
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]+175.13530932474
DeepCCS[M-H]-172.77730932474
DeepCCS[M-2H]-205.66530932474
DeepCCS[M+Na]+181.22830932474
AllCCS[M+H]+174.032859911
AllCCS[M+H-H2O]+170.832859911
AllCCS[M+NH4]+176.932859911
AllCCS[M+Na]+177.832859911
AllCCS[M-H]-163.832859911
AllCCS[M+Na-2H]-164.132859911
AllCCS[M+HCOO]-164.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-IodothyronamineNCCC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C13555.0Standard polar33892256
3-IodothyronamineNCCC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C12601.9Standard non polar33892256
3-IodothyronamineNCCC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C12595.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Iodothyronamine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN)C=C2I)C=C12556.8Semi standard non polar33892256
3-Iodothyronamine,1TMS,isomer #2C[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C12665.3Semi standard non polar33892256
3-Iodothyronamine,2TMS,isomer #1C[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C12645.2Semi standard non polar33892256
3-Iodothyronamine,2TMS,isomer #1C[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C12613.0Standard non polar33892256
3-Iodothyronamine,2TMS,isomer #1C[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C12744.3Standard polar33892256
3-Iodothyronamine,2TMS,isomer #2C[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C2831.8Semi standard non polar33892256
3-Iodothyronamine,2TMS,isomer #2C[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C2839.4Standard non polar33892256
3-Iodothyronamine,2TMS,isomer #2C[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C2925.1Standard polar33892256
3-Iodothyronamine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C12853.5Semi standard non polar33892256
3-Iodothyronamine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C12766.8Standard non polar33892256
3-Iodothyronamine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C12666.5Standard polar33892256
3-Iodothyronamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN)C=C2I)C=C12857.6Semi standard non polar33892256
3-Iodothyronamine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C12923.2Semi standard non polar33892256
3-Iodothyronamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C13175.5Semi standard non polar33892256
3-Iodothyronamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C13079.2Standard non polar33892256
3-Iodothyronamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C12948.9Standard polar33892256
3-Iodothyronamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C(C)(C)C3294.4Semi standard non polar33892256
3-Iodothyronamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C(C)(C)C3176.6Standard non polar33892256
3-Iodothyronamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C(C)(C)C3023.9Standard polar33892256
3-Iodothyronamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C13557.2Semi standard non polar33892256
3-Iodothyronamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C13321.7Standard non polar33892256
3-Iodothyronamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C12927.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Iodothyronamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9234000000-cbe7ce6b0b53901966172017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Iodothyronamine GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9544200000-abcf7fbd451095b060fd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Iodothyronamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Iodothyronamine 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 - 3-Iodothyronamine 10V, Positive-QTOFsplash10-0a4r-0009000000-cd25707825600657237e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 20V, Positive-QTOFsplash10-052r-0019000000-c676f1af5a1bbb019cf42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 40V, Positive-QTOFsplash10-0059-7290000000-a48ad0fe4a8b940c65942017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 10V, Negative-QTOFsplash10-0udi-0009000000-eee6542cdd26d5ee70542017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 20V, Negative-QTOFsplash10-0zfr-1409000000-cc1eb04889537ba7c4352017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 40V, Negative-QTOFsplash10-0a4i-9530000000-a68000570cc66dff41cc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 10V, Positive-QTOFsplash10-000i-0009000000-91d096588f74424973222021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 20V, Positive-QTOFsplash10-000i-0009000000-26545fb92394df44883f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 40V, Positive-QTOFsplash10-0159-1792000000-48cae08e0cf6af8bdb712021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 10V, Negative-QTOFsplash10-0udi-0009000000-5cbc314388be299c05f82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 20V, Negative-QTOFsplash10-0udi-0129000000-9707c1df1eff5eae73fd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Iodothyronamine 40V, Negative-QTOFsplash10-0a6r-8930000000-811a2969de1e7fb4e8d82021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.066 +/- 0.026 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000232 +/- 0.000014 uMAdult (>18 years old)BothType 2 diabetes details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Galli E, Marchini M, Saba A, Berti S, Tonacchera M, Vitti P, Scanlan TS, Iervasi G, Zucchi R: Detection of 3-iodothyronamine in human patients: a preliminary study. J Clin Endocrinol Metab. 2012 Jan;97(1):E69-74. doi: 10.1210/jc.2011-1115. Epub 2011 Oct 26. [PubMed:22031514 ]
Associated OMIM IDs
DrugBank IDNot Available
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 Link3-Iodothyronamine
METLIN IDNot Available
PubChem Compound9950514
PDB IDNot Available
ChEBI IDNot Available
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 ReferencesNot Available