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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-06-05 01:09:24 UTC

Update Date

2019-07-23 07:14:31 UTC

HMDB ID

HMDB0060524

Secondary Accession Numbers

HMDB60524

Metabolite Identification

Common Name

3-Iodothyronamine

Description

3-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

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

HMDB0060524
     RDKit          3D
3-Iodothyronamine
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.5717    0.8423    1.5317 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741    0.6485    1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532   -0.0757   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -0.2768   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -1.4383    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910   -1.6865   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2277   -0.7854   -0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247   -1.1596   -1.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859   -0.5885   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264   -0.5850    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138   -0.0062    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0919    0.5767    0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2959    1.1574    0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7494    0.5695   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497   -0.0124   -1.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958    0.3419   -1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.7738   -2.3447 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524    0.6114   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9955   -0.0308    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0797    1.1669    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361    0.0269    2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6981    1.6603    1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4401   -1.0795    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4477    0.4916   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -2.1670    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1781   -2.6137    0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652   -1.0356    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4818   -0.0040    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4882    1.1315    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4254    1.0220   -1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493    0.0022   -2.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    1.5221   -1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 16 18  2  0
 18  4  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
M  END


  Mrv1652304062013162D          

 18 19  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
  7 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060524

> <DATABASE_NAME>
hmdb

> <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_KEY>
XIINYOJWNGOUPF-UHFFFAOYSA-N

> <FORMULA>
C14H14INO2

> <MOLECULAR_WEIGHT>
355.1709

> <EXACT_MASS>
355.006922117

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
30.389707334132044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(2-aminoethyl)-2-iodophenoxy]phenol

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
2.8774073106812144

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.432175820049531

> <JCHEM_PKA_STRONGEST_BASIC>
10.040518767791866

> <JCHEM_POLAR_SURFACE_AREA>
55.480000000000004

> <JCHEM_REFRACTIVITY>
80.87060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-iodothyronamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060524
     RDKit          3D
3-Iodothyronamine
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.5717    0.8423    1.5317 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741    0.6485    1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532   -0.0757   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -0.2768   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -1.4383    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910   -1.6865   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2277   -0.7854   -0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247   -1.1596   -1.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859   -0.5885   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264   -0.5850    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138   -0.0062    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0919    0.5767    0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2959    1.1574    0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7494    0.5695   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497   -0.0124   -1.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958    0.3419   -1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.7738   -2.3447 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524    0.6114   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9955   -0.0308    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0797    1.1669    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361    0.0269    2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6981    1.6603    1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4401   -1.0795    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4477    0.4916   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -2.1670    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1781   -2.6137    0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652   -1.0356    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4818   -0.0040    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4882    1.1315    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4254    1.0220   -1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493    0.0022   -2.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    1.5221   -1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 16 18  2  0
 18  4  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  I   UNK     0       4.001 -10.010   0.000  0.00  0.00           I+0
HETATM   10  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -4.001 -10.010   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15    7                                                       
CONECT   17    5   18                                                       
CONECT   18   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060524
HETATM    1  N1  UNL     1       5.572   0.842   1.532  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.174   0.648   1.253  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.953  -0.076  -0.061  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.526  -0.277  -0.352  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.916  -1.438   0.103  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.591  -1.686  -0.134  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.228  -0.785  -0.848  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.525  -1.160  -1.009  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.686  -0.588  -0.646  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.026  -0.585   0.697  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.214  -0.006   1.087  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.092   0.577   0.201  1.00  0.00           C  
HETATM   13  O2  UNL     1      -6.296   1.157   0.647  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.749   0.570  -1.125  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.550  -0.012  -1.544  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.396   0.342  -1.280  1.00  0.00           C  
HETATM   17  I1  UNL     1      -0.700   1.774  -2.345  1.00  0.00           I  
HETATM   18  C14 UNL     1       1.752   0.611  -1.046  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.995  -0.031   1.922  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.080   1.167   0.676  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.736   0.027   2.068  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.698   1.660   1.213  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.440  -1.079   0.061  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.448   0.492  -0.867  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.517  -2.167   0.663  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.178  -2.614   0.249  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.365  -1.036   1.452  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.482  -0.004   2.148  1.00  0.00           H  
HETATM   29  H11 UNL     1      -6.488   1.131   1.620  1.00  0.00           H  
HETATM   30  H12 UNL     1      -5.425   1.022  -1.835  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.349   0.002  -2.628  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.204   1.522  -1.410  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5    5   18
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8   16
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   29
CONECT   14   15   15   30
CONECT   15   31
CONECT   16   17   18   18
CONECT   18   32
END

HMDB0060524
     RDKit          3D
3-Iodothyronamine
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.5717    0.8423    1.5317 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741    0.6485    1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532   -0.0757   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -0.2768   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -1.4383    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910   -1.6865   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2277   -0.7854   -0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247   -1.1596   -1.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859   -0.5885   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264   -0.5850    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138   -0.0062    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0919    0.5767    0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2959    1.1574    0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7494    0.5695   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497   -0.0124   -1.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958    0.3419   -1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    1.7738   -2.3447 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524    0.6114   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9955   -0.0308    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0797    1.1669    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361    0.0269    2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6981    1.6603    1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4401   -1.0795    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4477    0.4916   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -2.1670    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1781   -2.6137    0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652   -1.0356    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4818   -0.0040    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4882    1.1315    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4254    1.0220   -1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493    0.0022   -2.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    1.5221   -1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 16 18  2  0
 18  4  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
T(1)AM CPD	HMDB

Chemical Formula

C₁₄H₁₄INO₂

Average Molecular Weight

355.1709

Monoisotopic Molecular Weight

355.006922117

IUPAC Name

4-[4-(2-aminoethyl)-2-iodophenoxy]phenol

Traditional Name

3-iodothyronamine

CAS Registry Number

Not 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 Key

XIINYOJWNGOUPF-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21490071)

Cellular substructure

Membrane (HMDB: HMDB0060524)

Source

Endogenous

Endogenous (HMDB: HMDB0060524)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

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
Water Solubility	0.032 g/L	ALOGPS
logP	3.74	ALOGPS
logP	2.88	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.43	ChemAxon
pKa (Strongest Basic)	10.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.87 m³·mol⁻¹	ChemAxon
Polarizability	30.39 Å³	ChemAxon
Number of Rings	2	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]+	175.135	30932474
DeepCCS	[M-H]-	172.777	30932474
DeepCCS	[M-2H]-	205.665	30932474
DeepCCS	[M+Na]+	181.228	30932474
AllCCS	[M+H]+	174.0	32859911
AllCCS	[M+H-H2O]+	170.8	32859911
AllCCS	[M+NH4]+	176.9	32859911
AllCCS	[M+Na]+	177.8	32859911
AllCCS	[M-H]-	163.8	32859911
AllCCS	[M+Na-2H]-	164.1	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.87 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8753 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.75 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1044.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	301.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	112.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	389.8 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	387.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	652.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	861.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	359.0 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	915.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	300.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	412.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	332.6 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	55.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Iodothyronamine	NCCC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C1	3555.0	Standard polar	33892256
3-Iodothyronamine	NCCC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C1	2601.9	Standard non polar	33892256
3-Iodothyronamine	NCCC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C1	2595.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Iodothyronamine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN)C=C2I)C=C1	2556.8	Semi standard non polar	33892256
3-Iodothyronamine,1TMS,isomer #2	C[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1	2665.3	Semi standard non polar	33892256
3-Iodothyronamine,2TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1	2645.2	Semi standard non polar	33892256
3-Iodothyronamine,2TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1	2613.0	Standard non polar	33892256
3-Iodothyronamine,2TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1	2744.3	Standard polar	33892256
3-Iodothyronamine,2TMS,isomer #2	C[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C	2831.8	Semi standard non polar	33892256
3-Iodothyronamine,2TMS,isomer #2	C[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C	2839.4	Standard non polar	33892256
3-Iodothyronamine,2TMS,isomer #2	C[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C	2925.1	Standard polar	33892256
3-Iodothyronamine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1	2853.5	Semi standard non polar	33892256
3-Iodothyronamine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1	2766.8	Standard non polar	33892256
3-Iodothyronamine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1	2666.5	Standard polar	33892256
3-Iodothyronamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(CCN)C=C2I)C=C1	2857.6	Semi standard non polar	33892256
3-Iodothyronamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1	2923.2	Semi standard non polar	33892256
3-Iodothyronamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1	3175.5	Semi standard non polar	33892256
3-Iodothyronamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1	3079.2	Standard non polar	33892256
3-Iodothyronamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1	2948.9	Standard polar	33892256
3-Iodothyronamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C(C)(C)C	3294.4	Semi standard non polar	33892256
3-Iodothyronamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C(C)(C)C	3176.6	Standard non polar	33892256
3-Iodothyronamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCC1=CC=C(OC2=CC=C(O)C=C2)C(I)=C1)[Si](C)(C)C(C)(C)C	3023.9	Standard polar	33892256
3-Iodothyronamine,3TBDMS,isomer #1	CC(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=C1	3557.2	Semi standard non polar	33892256
3-Iodothyronamine,3TBDMS,isomer #1	CC(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=C1	3321.7	Standard non polar	33892256
3-Iodothyronamine,3TBDMS,isomer #1	CC(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=C1	2927.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Iodothyronamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9234000000-cbe7ce6b0b5390196617	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Iodothyronamine GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9544200000-abcf7fbd451095b060fd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Iodothyronamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Iodothyronamine 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 - 3-Iodothyronamine 10V, Positive-QTOF	splash10-0a4r-0009000000-cd25707825600657237e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 20V, Positive-QTOF	splash10-052r-0019000000-c676f1af5a1bbb019cf4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 40V, Positive-QTOF	splash10-0059-7290000000-a48ad0fe4a8b940c6594	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 10V, Negative-QTOF	splash10-0udi-0009000000-eee6542cdd26d5ee7054	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 20V, Negative-QTOF	splash10-0zfr-1409000000-cc1eb04889537ba7c435	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 40V, Negative-QTOF	splash10-0a4i-9530000000-a68000570cc66dff41cc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 10V, Positive-QTOF	splash10-000i-0009000000-91d096588f7442497322	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 20V, Positive-QTOF	splash10-000i-0009000000-26545fb92394df44883f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 40V, Positive-QTOF	splash10-0159-1792000000-48cae08e0cf6af8bdb71	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 10V, Negative-QTOF	splash10-0udi-0009000000-5cbc314388be299c05f8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 20V, Negative-QTOF	splash10-0udi-0129000000-9707c1df1eff5eae73fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Iodothyronamine 40V, Negative-QTOF	splash10-0a6r-8930000000-811a2969de1e7fb4e8d8	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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 and Quantified	0.066 +/- 0.026 uM	Adult (>18 years old)	Both	Normal	21490071	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000232 +/- 0.000014 uM	Adult (>18 years old)	Both	Type 2 diabetes	22031514	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 2
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

125853 (Diabetes mellitus type 2)

External Links

DrugBank ID

Not Available

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

3-Iodothyronamine

METLIN ID

Not Available

PubChem Compound

9950514

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

Not Available

Showing metabocard for 3-Iodothyronamine (HMDB0060524)

MOL for HMDB0060524 (3-Iodothyronamine)

3D MOL for HMDB0060524 (3-Iodothyronamine)

3D SDF for HMDB0060524 (3-Iodothyronamine)

3D-SDF for HMDB0060524 (3-Iodothyronamine)

PDB for HMDB0060524 (3-Iodothyronamine)

3D PDB for HMDB0060524 (3-Iodothyronamine)

SMILES for HMDB0060524 (3-Iodothyronamine)

INCHI for HMDB0060524 (3-Iodothyronamine)

Structure for HMDB0060524 (3-Iodothyronamine)

3D Structure for HMDB0060524 (3-Iodothyronamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra