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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:16:27 UTC
Update Date2021-09-26 22:53:29 UTC
HMDB IDHMDB0245177
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Iodo-l-phenylalanine
Description2-Iodo-l-phenylalanine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on 2-Iodo-l-phenylalanine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-iodo-l-phenylalanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Iodo-l-phenylalanine 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
SynonymsNot Available
Chemical FormulaC9H10INO2
Average Molecular Weight291.088
Monoisotopic Molecular Weight290.97562
IUPAC Name2-amino-3-(2-iodophenyl)propanoic acid
Traditional Name2-amino-3-(2-iodophenyl)propanoic acid
CAS Registry NumberNot Available
SMILES
NC(CC1=CC=CC=C1I)C(O)=O
InChI Identifier
InChI=1S/C9H10INO2/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)
InChI KeyBKXVGLPBXYBDDM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • Aralkylamine
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organohalogen compound
  • Organoiodide
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • 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
logP-1.2ALOGPS
logP-0.26ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.48 m³·mol⁻¹ChemAxon
Polarizability22.24 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]+147.61730932474
DeepCCS[M-H]-143.7930932474
DeepCCS[M-2H]-180.930932474
DeepCCS[M+Na]+156.4430932474
AllCCS[M+H]+159.832859911
AllCCS[M+H-H2O]+156.132859911
AllCCS[M+NH4]+163.232859911
AllCCS[M+Na]+164.132859911
AllCCS[M-H]-149.732859911
AllCCS[M+Na-2H]-151.132859911
AllCCS[M+HCOO]-152.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Iodo-l-phenylalanineNC(CC1=CC=CC=C1I)C(O)=O3023.7Standard polar33892256
2-Iodo-l-phenylalanineNC(CC1=CC=CC=C1I)C(O)=O1873.1Standard non polar33892256
2-Iodo-l-phenylalanineNC(CC1=CC=CC=C1I)C(O)=O2113.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Iodo-l-phenylalanine,2TMS,isomer #1C[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C1968.3Semi standard non polar33892256
2-Iodo-l-phenylalanine,2TMS,isomer #1C[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C1967.3Standard non polar33892256
2-Iodo-l-phenylalanine,2TMS,isomer #1C[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C2022.7Standard polar33892256
2-Iodo-l-phenylalanine,2TMS,isomer #2C[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C2127.5Semi standard non polar33892256
2-Iodo-l-phenylalanine,2TMS,isomer #2C[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C2108.0Standard non polar33892256
2-Iodo-l-phenylalanine,2TMS,isomer #2C[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C2204.9Standard polar33892256
2-Iodo-l-phenylalanine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C)[Si](C)(C)C2168.9Semi standard non polar33892256
2-Iodo-l-phenylalanine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C)[Si](C)(C)C2146.1Standard non polar33892256
2-Iodo-l-phenylalanine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C)[Si](C)(C)C1991.2Standard polar33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C(C)(C)C2435.5Semi standard non polar33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C(C)(C)C2503.4Standard non polar33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C(C)(C)C2293.6Standard polar33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C(C)(C)C2559.5Semi standard non polar33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C(C)(C)C2549.6Standard non polar33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C(C)(C)C2378.0Standard polar33892256
2-Iodo-l-phenylalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2817.3Semi standard non polar33892256
2-Iodo-l-phenylalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2800.1Standard non polar33892256
2-Iodo-l-phenylalanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2334.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-4090000000-0501463b5147f2c5f2df2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 10V, Positive-QTOFsplash10-006w-0090000000-36235136908cda3b5d152021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 20V, Positive-QTOFsplash10-014i-0090000000-a4cd42aac3bb19e388ad2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 40V, Positive-QTOFsplash10-014i-1090000000-574431fb7e02561e5e0a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 10V, Negative-QTOFsplash10-002r-0090000000-433587abfb60aeeb4f3c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 20V, Negative-QTOFsplash10-004i-0390000000-a7832a8cf049e0af97932021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 40V, Negative-QTOFsplash10-004i-0930000000-b53a15a3191573bdbf3d2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-12Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3169163
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3948024
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 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 ]