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Showing metabocard for Iobenguane (HMDB0253507)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 12:04:48 UTC
Update Date2021-09-26 23:06:46 UTC
HMDB IDHMDB0253507
Secondary Accession NumbersNone
Metabolite Identification
Common NameIobenguane
DescriptionIobenguane 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0253507 (Iobenguane)

  Mrv0541 02241212482D          

 12 12  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
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3D MOL for HMDB0253507 (Iobenguane)

HMDB0253507
     RDKit          3D
Iobenguane
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.3072   -1.8309   -0.1388 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6224   -0.5852   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871    0.6119   -0.3991 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570   -0.5860   -0.0757 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176    0.6494   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    0.4005   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    1.4975   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0551    1.3726   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    0.1213    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7730   -0.9629    0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6139   -2.8902    0.2673 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4024   -0.8492    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6854   -2.2017   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4217   -2.3390    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425    1.5281   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3109    0.5498   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877    1.2375    0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8134    1.2123   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919    2.5068   -0.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    2.2527   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7220   -0.0021    0.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -1.6931    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12  6  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 12 22  1  0
M  END
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3D SDF for HMDB0253507 (Iobenguane)

  Mrv0541 02241212482D          

 12 12  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253507

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C8H10IN3

> <MOLECULAR_WEIGHT>
275.0896

> <EXACT_MASS>
274.991940755

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.92774033036308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3-iodophenyl)methyl]guanidine

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.6402546463333332

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
11.270847308527944

> <JCHEM_POLAR_SURFACE_AREA>
64.39999999999999

> <JCHEM_REFRACTIVITY>
58.31569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
meta iodobenzylguanidine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0253507 (Iobenguane)

HMDB0253507
     RDKit          3D
Iobenguane
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.3072   -1.8309   -0.1388 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6224   -0.5852   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871    0.6119   -0.3991 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570   -0.5860   -0.0757 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176    0.6494   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    0.4005   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    1.4975   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0551    1.3726   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    0.1213    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7730   -0.9629    0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6139   -2.8902    0.2673 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4024   -0.8492    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6854   -2.2017   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4217   -2.3390    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425    1.5281   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3109    0.5498   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877    1.2375    0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8134    1.2123   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919    2.5068   -0.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    2.2527   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7220   -0.0021    0.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -1.6931    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12  6  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0253507 (Iobenguane)

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
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3D PDB for HMDB0253507 (Iobenguane)

COMPND    HMDB0253507
HETATM    1  N1  UNL     1       3.307  -1.831  -0.139  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.622  -0.585  -0.200  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.387   0.612  -0.399  1.00  0.00           N  
HETATM    4  N3  UNL     1       1.357  -0.586  -0.076  1.00  0.00           N  
HETATM    5  C2  UNL     1       0.618   0.649  -0.131  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.851   0.400  -0.058  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.682   1.498  -0.100  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.055   1.373  -0.040  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.629   0.121   0.066  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.773  -0.963   0.106  1.00  0.00           C  
HETATM   11  I1  UNL     1      -3.614  -2.890   0.267  1.00  0.00           I  
HETATM   12  C8  UNL     1      -1.402  -0.849   0.046  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.685  -2.202  -1.037  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.422  -2.339   0.754  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.042   1.528  -0.096  1.00  0.00           H  
HETATM   16  H4  UNL     1       4.311   0.550  -0.860  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.888   1.237   0.770  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.813   1.212  -1.055  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.292   2.507  -0.183  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.701   2.253  -0.074  1.00  0.00           H  
HETATM   21  H9  UNL     1      -4.722  -0.002   0.116  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.731  -1.693   0.078  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3    4    4
CONECT    3   15   16
CONECT    4    5
CONECT    5    6   17   18
CONECT    6    7    7   12
CONECT    7    8   19
CONECT    8    9    9   20
CONECT    9   10   21
CONECT   10   11   12   12
CONECT   12   22
END
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SMILES for HMDB0253507 (Iobenguane)

NC(N)=NCC1=CC(I)=CC=C1
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INCHI for HMDB0253507 (Iobenguane)

InChI=1S/C8H10IN3/c9-7-3-1-2-6(4-7)5-12-8(10)11/h1-4H,5H2,(H4,10,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(3-iodo-(131I)benzyl)guanidineMeSH
m IodobenzylguanidineMeSH
Meta-iodobenzylguanidineMeSH
123I labeled 3-iodobenzylguanidineMeSH
3 Iodobenzylguanidine, 125I labeledMeSH
MIBGMeSH
125I labeled 3-iodobenzylguanidineMeSH
3 IodobenzylguanidineMeSH
3 Iodobenzylguanidine, 123I labeledMeSH
3-IodobenzylguanidineMeSH
3-Iodobenzylguanidine, 123I labeledMeSH
3-Iodobenzylguanidine, 125I labeledMeSH
m-IodobenzylguanidineMeSH
Iobenguane (131I)MeSH
Meta iodobenzylguanidineMeSH
Chemical FormulaC8H10IN3
Average Molecular Weight275.0896
Monoisotopic Molecular Weight274.991940755
IUPAC Name2-[(3-iodophenyl)methyl]guanidine
Traditional Namemeta iodobenzylguanidine
CAS Registry NumberNot 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 KeyPDWUPXJEEYOOTR-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentIodobenzenes
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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
Predicted Chromatographic Properties
Spectra
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 IDDB06704
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 LinkIobenguane
METLIN IDNot Available
PubChem Compound60860
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 ]