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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:04:48 UTC

Update Date

2021-09-26 23:06:46 UTC

HMDB ID

HMDB0253507

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Iobenguane

Description

Iobenguane belongs to the class of organic compounds known as iodobenzenes. These are aromatic compounds containing one or more iodine atoms attached to a benzene. Iodine 123 is a cyclotron-produced radionuclide that decays to Te 123 by electron capture. The radioisotope used can either be iodine-123 for imaging or iodine-131 for destruction of tissues that metabolize noradrenaline. Images are produced by a I123 MIBG scintigraphy. Iobenguane is a very strong basic compound (based on its pKa). AdreView is a diagnostic radiopharmaceutical which contains a small quantity of iobenguane that is not expected to produce a pharmacodynamic effect. Patients with renal insufficiency may experience increased radiation exposure and impaired imaging results. Less than 10% of the dose is metabolized into m-iodohippuric acid (MIHA). The most common adverse reactions, dizziness, rash, pruritis, flushing, headache, and injection site hemorrhage occurred in < 1.3% of patients. Structure of iobenguane is similar to noradrenaline so it can be taken up by adrenergic tissue in the adrenal medulla, liver, heart, and spleen. FDA approved on September 19, 2008. Oral, rabbit: LD50 = 3200 mg/kg;. This compound has been identified in human blood as reported by (PMID: 31557052 ). Iobenguane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Iobenguane 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         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  I   UNK     0       1.334   3.850   0.000  0.00  0.00           I+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -4.001  -2.310   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3-iodo-(131I)benzyl)guanidine	MeSH
m Iodobenzylguanidine	MeSH
Meta-iodobenzylguanidine	MeSH
123I labeled 3-iodobenzylguanidine	MeSH
3 Iodobenzylguanidine, 125I labeled	MeSH
MIBG	MeSH
125I labeled 3-iodobenzylguanidine	MeSH
3 Iodobenzylguanidine	MeSH
3 Iodobenzylguanidine, 123I labeled	MeSH
3-Iodobenzylguanidine	MeSH
3-Iodobenzylguanidine, 123I labeled	MeSH
3-Iodobenzylguanidine, 125I labeled	MeSH
m-Iodobenzylguanidine	MeSH
Iobenguane (131I)	MeSH
Meta iodobenzylguanidine	MeSH

Chemical Formula

C₈H₁₀IN₃

Average Molecular Weight

275.0896

Monoisotopic Molecular Weight

274.991940755

IUPAC Name

2-[(3-iodophenyl)methyl]guanidine

Traditional Name

meta iodobenzylguanidine

CAS Registry Number

Not Available

SMILES

NC(N)=NCC1=CC(I)=CC=C1

InChI Identifier

InChI=1S/C8H10IN3/c9-7-3-1-2-6(4-7)5-12-8(10)11/h1-4H,5H2,(H4,10,11,12)

InChI Key

PDWUPXJEEYOOTR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iodobenzenes. These are aromatic compounds containing one or more iodine atoms attached to a benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Iodobenzenes

Alternative Parents

Substituents

Iodobenzene
Aryl iodide
Aryl halide
Guanidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organoiodide
Organohalogen compound
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)

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	1.53	ALOGPS
logP	1.64	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	11.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.32 m³·mol⁻¹	ChemAxon
Polarizability	21.93 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]+	148.501	30932474
DeepCCS	[M-H]-	145.477	30932474
DeepCCS	[M-2H]-	182.166	30932474
DeepCCS	[M+Na]+	157.703	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	151.5	32859911
AllCCS	[M+NH4]+	158.8	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	146.6	32859911
AllCCS	[M+Na-2H]-	148.2	32859911
AllCCS	[M+HCOO]-	150.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Iobenguane	NC(N)=NCC1=CC(I)=CC=C1	3021.8	Standard polar	33892256
Iobenguane	NC(N)=NCC1=CC(I)=CC=C1	1833.8	Standard non polar	33892256
Iobenguane	NC(N)=NCC1=CC(I)=CC=C1	2094.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Iobenguane,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCC1=CC=CC(I)=C1	2072.0	Semi standard non polar	33892256
Iobenguane,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCC1=CC=CC(I)=C1	1921.7	Standard non polar	33892256
Iobenguane,1TMS,isomer #1	C[Si](C)(C)NC(N)=NCC1=CC=CC(I)=C1	2795.8	Standard polar	33892256
Iobenguane,2TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N[Si](C)(C)C	2216.6	Semi standard non polar	33892256
Iobenguane,2TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N[Si](C)(C)C	1895.2	Standard non polar	33892256
Iobenguane,2TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N[Si](C)(C)C	2600.5	Standard polar	33892256
Iobenguane,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCC1=CC=CC(I)=C1)[Si](C)(C)C	2159.0	Semi standard non polar	33892256
Iobenguane,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCC1=CC=CC(I)=C1)[Si](C)(C)C	2083.3	Standard non polar	33892256
Iobenguane,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NCC1=CC=CC(I)=C1)[Si](C)(C)C	2746.9	Standard polar	33892256
Iobenguane,3TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	2210.9	Semi standard non polar	33892256
Iobenguane,3TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	2089.3	Standard non polar	33892256
Iobenguane,3TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	2390.9	Standard polar	33892256
Iobenguane,4TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2255.1	Semi standard non polar	33892256
Iobenguane,4TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2286.7	Standard non polar	33892256
Iobenguane,4TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2173.5	Standard polar	33892256
Iobenguane,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCC1=CC=CC(I)=C1	2289.6	Semi standard non polar	33892256
Iobenguane,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCC1=CC=CC(I)=C1	2167.3	Standard non polar	33892256
Iobenguane,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NCC1=CC=CC(I)=C1	2914.6	Standard polar	33892256
Iobenguane,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N[Si](C)(C)C(C)(C)C	2640.1	Semi standard non polar	33892256
Iobenguane,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N[Si](C)(C)C(C)(C)C	2342.0	Standard non polar	33892256
Iobenguane,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N[Si](C)(C)C(C)(C)C	2656.8	Standard polar	33892256
Iobenguane,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCC1=CC=CC(I)=C1)[Si](C)(C)C(C)(C)C	2517.4	Semi standard non polar	33892256
Iobenguane,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCC1=CC=CC(I)=C1)[Si](C)(C)C(C)(C)C	2494.5	Standard non polar	33892256
Iobenguane,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NCC1=CC=CC(I)=C1)[Si](C)(C)C(C)(C)C	2896.2	Standard polar	33892256
Iobenguane,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2804.2	Semi standard non polar	33892256
Iobenguane,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2675.7	Standard non polar	33892256
Iobenguane,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2611.3	Standard polar	33892256
Iobenguane,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3027.6	Semi standard non polar	33892256
Iobenguane,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2998.3	Standard non polar	33892256
Iobenguane,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=CC(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2513.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Iobenguane GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-6390000000-640361ed282a3fc2307a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iobenguane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Iobenguane 10V, Positive-QTOF	splash10-004i-0090000000-b3e76b79f5d46e05883e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 20V, Positive-QTOF	splash10-0059-0090000000-1911bfc0197ac56701cd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 40V, Positive-QTOF	splash10-0006-9350000000-c62170aa98fc5ba091f4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 10V, Negative-QTOF	splash10-0089-0090000000-6e8494d4f9d207c202a7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 20V, Negative-QTOF	splash10-001i-0090000000-6466be43f7795b19bee3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 40V, Negative-QTOF	splash10-0006-9140000000-0579f63118d89ba7131e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 10V, Positive-QTOF	splash10-016r-0090000000-2af9c404886fbbb4e3df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 20V, Positive-QTOF	splash10-014i-0090000000-642fc9e3486633795624	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 40V, Positive-QTOF	splash10-014i-1590000000-f167610a98c4d564aa14	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 10V, Negative-QTOF	splash10-0036-7090000000-4d662d91bb96651374ba	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 20V, Negative-QTOF	splash10-0006-9110000000-e869684000929e923df1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iobenguane 40V, Negative-QTOF	splash10-004i-4900000000-ebee621b00db762eb0ef	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

DB06704

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Iobenguane

METLIN ID

Not Available

PubChem Compound

60860

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 Iobenguane (HMDB0253507)

MOL for HMDB0253507 (Iobenguane)

3D MOL for HMDB0253507 (Iobenguane)

3D SDF for HMDB0253507 (Iobenguane)

3D-SDF for HMDB0253507 (Iobenguane)

PDB for HMDB0253507 (Iobenguane)

3D PDB for HMDB0253507 (Iobenguane)

SMILES for HMDB0253507 (Iobenguane)

INCHI for HMDB0253507 (Iobenguane)

Structure for HMDB0253507 (Iobenguane)

3D Structure for HMDB0253507 (Iobenguane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra