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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:16:27 UTC

Update Date

2021-09-26 22:53:29 UTC

HMDB ID

HMDB0245177

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Iodo-l-phenylalanine

Description

2-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 a significant number of 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM   13  I   UNK     0      -1.334   2.310   0.000  0.00  0.00           I+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    4                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₁₀INO₂

Average Molecular Weight

291.088

Monoisotopic Molecular Weight

290.97562

IUPAC Name

2-amino-3-(2-iodophenyl)propanoic acid

Traditional Name

2-amino-3-(2-iodophenyl)propanoic acid

CAS Registry Number

Not 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 Key

BKXVGLPBXYBDDM-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.2	ALOGPS
logP	-0.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.48 m³·mol⁻¹	ChemAxon
Polarizability	22.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.617	30932474
DeepCCS	[M-H]-	143.79	30932474
DeepCCS	[M-2H]-	180.9	30932474
DeepCCS	[M+Na]+	156.44	30932474
AllCCS	[M+H]+	159.8	32859911
AllCCS	[M+H-H2O]+	156.1	32859911
AllCCS	[M+NH4]+	163.2	32859911
AllCCS	[M+Na]+	164.1	32859911
AllCCS	[M-H]-	149.7	32859911
AllCCS	[M+Na-2H]-	151.1	32859911
AllCCS	[M+HCOO]-	152.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.0092 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.97 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	600.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	285.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	300.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	711.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	690.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	240.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	758.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	502.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	437.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	229.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Iodo-l-phenylalanine	NC(CC1=CC=CC=C1I)C(O)=O	3023.7	Standard polar	33892256
2-Iodo-l-phenylalanine	NC(CC1=CC=CC=C1I)C(O)=O	1873.1	Standard non polar	33892256
2-Iodo-l-phenylalanine	NC(CC1=CC=CC=C1I)C(O)=O	2113.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Iodo-l-phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C	1968.3	Semi standard non polar	33892256
2-Iodo-l-phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C	1967.3	Standard non polar	33892256
2-Iodo-l-phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C	2022.7	Standard polar	33892256
2-Iodo-l-phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C	2127.5	Semi standard non polar	33892256
2-Iodo-l-phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C	2108.0	Standard non polar	33892256
2-Iodo-l-phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C	2204.9	Standard polar	33892256
2-Iodo-l-phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C)[Si](C)(C)C	2168.9	Semi standard non polar	33892256
2-Iodo-l-phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C)[Si](C)(C)C	2146.1	Standard non polar	33892256
2-Iodo-l-phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1I)N([Si](C)(C)C)[Si](C)(C)C	1991.2	Standard polar	33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C(C)(C)C	2435.5	Semi standard non polar	33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C(C)(C)C	2503.4	Standard non polar	33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1I)C(=O)O[Si](C)(C)C(C)(C)C	2293.6	Standard polar	33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C(C)(C)C	2559.5	Semi standard non polar	33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C(C)(C)C	2549.6	Standard non polar	33892256
2-Iodo-l-phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1I)C(=O)O)[Si](C)(C)C(C)(C)C	2378.0	Standard polar	33892256
2-Iodo-l-phenylalanine,3TBDMS,isomer #1	CC(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)C	2817.3	Semi standard non polar	33892256
2-Iodo-l-phenylalanine,3TBDMS,isomer #1	CC(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)C	2800.1	Standard non polar	33892256
2-Iodo-l-phenylalanine,3TBDMS,isomer #1	CC(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)C	2334.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-4090000000-0501463b5147f2c5f2df	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Iodo-l-phenylalanine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 10V, Positive-QTOF	splash10-006w-0090000000-36235136908cda3b5d15	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 20V, Positive-QTOF	splash10-014i-0090000000-a4cd42aac3bb19e388ad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 40V, Positive-QTOF	splash10-014i-1090000000-574431fb7e02561e5e0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 10V, Negative-QTOF	splash10-002r-0090000000-433587abfb60aeeb4f3c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 20V, Negative-QTOF	splash10-004i-0390000000-a7832a8cf049e0af9793	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Iodo-l-phenylalanine 40V, Negative-QTOF	splash10-004i-0930000000-b53a15a3191573bdbf3d	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3169163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3948024

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for 2-Iodo-l-phenylalanine (HMDB0245177)

MOL for HMDB0245177 (2-Iodo-l-phenylalanine)

3D MOL for HMDB0245177 (2-Iodo-l-phenylalanine)

3D SDF for HMDB0245177 (2-Iodo-l-phenylalanine)

3D-SDF for HMDB0245177 (2-Iodo-l-phenylalanine)

PDB for HMDB0245177 (2-Iodo-l-phenylalanine)

3D PDB for HMDB0245177 (2-Iodo-l-phenylalanine)

SMILES for HMDB0245177 (2-Iodo-l-phenylalanine)

INCHI for HMDB0245177 (2-Iodo-l-phenylalanine)

Structure for HMDB0245177 (2-Iodo-l-phenylalanine)

3D Structure for HMDB0245177 (2-Iodo-l-phenylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra