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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-11-15 21:04:30 UTC

HMDB ID

HMDB0000582

Secondary Accession Numbers

HMDB0000627
HMDB00582
HMDB00627

Metabolite Identification

Common Name

3,5-Diiodothyronine

Description

3,5-Diiodothyronine, also known as 3,5-T2, belongs to the class of organic compounds known as phenylalanines 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. It is also a member of the class of compounds known as iodothyronines. Iodothyronines are phenolic amino acids with iodine substituents. 3,5-Diiodothyronine is a metabolite of the two main thyroid hormones T3 and T4 (thyroxine and triiodo-L-thyronine). It is a biologically active iodothyronine with mitochondria and bioenergetic mechanisms being the major targets of 3,5-T2. Nanomolar concentrations of 3,5-T2 significantly increases cytochrome oxidase (COX) activity (PMID: 30090086 ). It increases COX activity by preventing the interaction of adenosine triphosphate (ATP) as an allosteric inhibitor. At 1 pM concentration, 3,5-T2 stimulates oxygen consumption more rapidly than thyroxine (T3). A case report involving two human participants revealed that administration of 3,5-T2 to humans (1-5 ug/kg BW) rapidly (after 4-6 h) increased resting metabolic rate. Chronic 3,5-T2 administration (28 days, approximately 5 ug/kg BW) increased resting metabolic rate by approximately 15% and decreased body weight by approximately 4 kg in both participants (PMID: 22217997 ). 3,5-T2 stimulates the thyroid receptor (TR)-beta receptor for thyroid hormones and thus increases energy expenditure. It has agonistic (thyromimetic) effects on myocardial tissue and on the pituitary, which results in 3,5-T2 suppressing thyroid stimulating hormone release.

Structure

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

HMDB0246056
     RDKit          3D
3,5-Diiodo-L-thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.9305   -0.4025    2.2199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6196   -0.8834    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753    0.1338   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696    0.3638   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4990   -0.4263   -1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -0.2250   -1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6424   -1.4554   -3.2545 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    0.7730   -1.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8459    0.9420   -1.5005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514    0.3522   -0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.5471    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -1.1392    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545   -0.8530    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943   -1.4734    0.5828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3424    0.0548   -0.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853    0.6524   -1.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    1.5708   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086    3.0430    0.7304 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141    1.3440    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0626   -0.9943    1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4983   -0.6904    2.4775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9396   -1.4388    0.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235   -1.2217    2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5122    0.2741    2.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2575   -1.8823    0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232    1.0794    0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -0.3008   -0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899   -1.2075   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -0.8305    0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473   -1.8556    1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040   -1.0621    1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3149    0.2720   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3461    1.3520   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527    1.9734    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8079   -1.1733   -0.5669 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  1  0
 17 19  2  0
  2 20  1  0
 20 21  2  0
 20 22  1  0
 19  4  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
 22 35  1  0
M  END


  Mrv1652305261923582D          

 22 23  0  0  0  0            999 V2000
    9.2317   -5.2562    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   12.0896   -5.2562    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   10.6607   -4.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2317   -9.3812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6607   -9.3812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5185   -2.7812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2317   -7.7312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6607   -7.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9462   -8.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6607   -6.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3751   -6.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9462   -6.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6607   -5.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9462   -5.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3751   -5.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9462   -8.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3751   -4.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3751   -3.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0896   -4.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0896   -2.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8041   -4.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8041   -3.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  0  0  0  0
  3 13  1  0  0  0  0
  3 17  1  0  0  0  0
  4 16  1  0  0  0  0
  5 16  2  0  0  0  0
  6 22  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000582

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)

> <INCHI_KEY>
ZHSOTLOTTDYIIK-UHFFFAOYSA-N

> <FORMULA>
C15H13I2NO4

> <MOLECULAR_WEIGHT>
525.077

> <EXACT_MASS>
524.893394749

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
38.69552149080478

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
1.86961479590096

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.867820908725388

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.33171965894530775

> <JCHEM_PKA_STRONGEST_BASIC>
9.232461570060185

> <JCHEM_POLAR_SURFACE_AREA>
92.78

> <JCHEM_REFRACTIVITY>
100.06299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-diiodo-dl-thryronine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246056
     RDKit          3D
3,5-Diiodo-L-thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.9305   -0.4025    2.2199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6196   -0.8834    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753    0.1338   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696    0.3638   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4990   -0.4263   -1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -0.2250   -1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6424   -1.4554   -3.2545 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    0.7730   -1.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8459    0.9420   -1.5005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514    0.3522   -0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.5471    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -1.1392    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545   -0.8530    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943   -1.4734    0.5828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3424    0.0548   -0.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853    0.6524   -1.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    1.5708   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086    3.0430    0.7304 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141    1.3440    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0626   -0.9943    1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4983   -0.6904    2.4775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9396   -1.4388    0.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235   -1.2217    2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5122    0.2741    2.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2575   -1.8823    0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232    1.0794    0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -0.3008   -0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899   -1.2075   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -0.8305    0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473   -1.8556    1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040   -1.0621    1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3149    0.2720   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3461    1.3520   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527    1.9734    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8079   -1.1733   -0.5669 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  1  0
 17 19  2  0
  2 20  1  0
 20 21  2  0
 20 22  1  0
 19  4  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
 22 35  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  I   UNK     0      17.233  -9.812   0.000  0.00  0.00           I+0
HETATM    2  I   UNK     0      22.567  -9.812   0.000  0.00  0.00           I+0
HETATM    3  O   UNK     0      19.900  -8.272   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.233 -17.512   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      19.900 -17.512   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      25.235  -5.192   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      17.233 -14.432   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      19.900 -14.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.566 -15.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.900 -12.892   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.234 -12.122   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.566 -12.122   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.900  -9.812   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.566 -10.582   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.234 -10.582   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.566 -16.742   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.234  -7.502   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.234  -5.962   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.567  -8.272   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.567  -5.192   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.901  -7.502   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.901  -5.962   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3   13   17                                                       
CONECT    4   16                                                            
CONECT    5   16                                                            
CONECT    6   22                                                            
CONECT    7    9                                                            
CONECT    8    9   10                                                       
CONECT    9    7    8   16                                                  
CONECT   10    8   11   12                                                  
CONECT   11   10   15                                                       
CONECT   12   10   14                                                       
CONECT   13    3   14   15                                                  
CONECT   14    1   12   13                                                  
CONECT   15    2   11   13                                                  
CONECT   16    4    5    9                                                  
CONECT   17    3   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   22                                                       
CONECT   22    6   20   21                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0000582
HETATM    1  N1  UNL     1      -5.237   2.155  -0.111  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.176   1.206   0.242  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.918   1.720  -0.375  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.753   0.838  -0.092  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.432  -0.174  -0.973  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.349  -0.969  -0.670  1.00  0.00           C  
HETATM    7  I1  UNL     1       0.197  -2.538  -1.978  1.00  0.00           I  
HETATM    8  C6  UNL     1       0.394  -0.770   0.469  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.490  -1.568   0.783  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.767  -1.284   0.380  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.059  -0.174  -0.373  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.363   0.102  -0.775  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.382  -0.741  -0.419  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.709  -0.472  -0.820  1.00  0.00           O  
HETATM   15  C11 UNL     1       5.093  -1.856   0.338  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.796  -2.122   0.732  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.082   0.238   1.355  1.00  0.00           C  
HETATM   18  I2  UNL     1       1.217   0.555   3.110  1.00  0.00           I  
HETATM   19  C14 UNL     1      -1.000   1.038   1.060  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.525  -0.139  -0.218  1.00  0.00           C  
HETATM   21  O3  UNL     1      -5.595  -0.292  -0.862  1.00  0.00           O  
HETATM   22  O4  UNL     1      -3.766  -1.269   0.001  1.00  0.00           O  
HETATM   23  H1  UNL     1      -4.808   3.105  -0.141  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.948   2.162   0.641  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.102   1.269   1.365  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.703   2.754  -0.085  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.043   1.737  -1.493  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.027  -0.332  -1.888  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.285   0.514  -0.674  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.604   0.978  -1.371  1.00  0.00           H  
HETATM   31  H9  UNL     1       7.333   0.085  -0.250  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.904  -2.521   0.617  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.603  -3.018   1.333  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.232   1.821   1.760  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.662  -2.035  -0.619  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3   20   25
CONECT    3    4   26   27
CONECT    4    5    5   19
CONECT    5    6   28
CONECT    6    7    8    8
CONECT    8    9   17
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   15
CONECT   14   31
CONECT   15   16   16   32
CONECT   16   33
CONECT   17   18   19   19
CONECT   19   34
CONECT   20   21   21   22
CONECT   22   35
END

HMDB0246056
     RDKit          3D
3,5-Diiodo-L-thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.9305   -0.4025    2.2199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6196   -0.8834    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753    0.1338   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696    0.3638   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4990   -0.4263   -1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -0.2250   -1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6424   -1.4554   -3.2545 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    0.7730   -1.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8459    0.9420   -1.5005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514    0.3522   -0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.5471    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -1.1392    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545   -0.8530    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943   -1.4734    0.5828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3424    0.0548   -0.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853    0.6524   -1.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    1.5708   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2086    3.0430    0.7304 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141    1.3440    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0626   -0.9943    1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4983   -0.6904    2.4775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9396   -1.4388    0.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235   -1.2217    2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5122    0.2741    2.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2575   -1.8823    0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232    1.0794    0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -0.3008   -0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899   -1.2075   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -0.8305    0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473   -1.8556    1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040   -1.0621    1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3149    0.2720   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3461    1.3520   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527    1.9734    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8079   -1.1733   -0.5669 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  1  0
 17 19  2  0
  2 20  1  0
 20 21  2  0
 20 22  1  0
 19  4  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
 22 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
35-Diiodothyronine	HMDB
(3,5-Diiodo-4-(-p-hydroxyphenoxy)phenyl)-alanine	HMDB
3',5'-Diiodothyronine	HMDB
3,5-Diiodo-D-thyronine	HMDB
3,5-Diiodo-DL-thryronine	HMDB
3,5-Diiodo-DL-thyronine	HMDB
3,5-Diiodo-L-thyronine	HMDB
3,5-T2	HMDB
4-(4-Hydroxyphenoxy)-3,5-diiodophenylalanine	HMDB
D-O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine	HMDB
Diiodo-L-thyronine	HMDB
Diiodothyronine	HMDB
DL-3,5-Diiodothyronine	HMDB
DL-Diiodothyronine	HMDB
L-3,5-Diiodothyronine	HMDB
L-O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine	HMDB
O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine	HMDB
3,5-Diiodothyronine, (L)-isomer	HMDB
3,5-Diiodothyronine, (DL)-isomer	HMDB
2-Amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoate	HMDB
3,5-Diiodothyronine	MeSH

Chemical Formula

C₁₅H₁₃I₂NO₄

Average Molecular Weight

525.077

Monoisotopic Molecular Weight

524.893394749

IUPAC Name

2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid

Traditional Name

3,5-diiodo-dl-thryronine

CAS Registry Number

534-51-0

SMILES

NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O

InChI Identifier

InChI=1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)

InChI Key

ZHSOTLOTTDYIIK-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
Diphenylether
Diaryl ether
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
Phenoxy compound
Phenol ether
Iodobenzene
Halobenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Benzenoid
Monocyclic benzene moiety
Amino acid
Ether
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary aliphatic amine
Organohalogen compound
Organoiodide
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

Not Available

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	186.44	30932474
[M+H]+	MetCCS_train_pos	198.208	30932474
[M-H]-	Not Available	186.44	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000021
[M+H]+	Not Available	198.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000021

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	0.45	ALOGPS
logP	1.87	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	0.33	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.06 m³·mol⁻¹	ChemAxon
Polarizability	38.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	195.947	32859911
AllCCS	[M-H]-	184.345	32859911
DeepCCS	[M+H]+	189.085	30932474
DeepCCS	[M-H]-	186.727	30932474
DeepCCS	[M-2H]-	219.612	30932474
DeepCCS	[M+Na]+	195.178	30932474
AllCCS	[M+H]+	195.9	32859911
AllCCS	[M+H-H2O]+	193.9	32859911
AllCCS	[M+NH4]+	197.9	32859911
AllCCS	[M+Na]+	198.4	32859911
AllCCS	[M-H]-	184.3	32859911
AllCCS	[M+Na-2H]-	185.4	32859911
AllCCS	[M+HCOO]-	186.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Diiodothyronine	NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O	4479.3	Standard polar	33892256
3,5-Diiodothyronine	NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O	3212.9	Standard non polar	33892256
3,5-Diiodothyronine	NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O	3486.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Diiodothyronine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(N)C(=O)O)C=C2I)C=C1	3202.0	Semi standard non polar	33892256
3,5-Diiodothyronine,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1	3216.0	Semi standard non polar	33892256
3,5-Diiodothyronine,1TMS,isomer #3	C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O	3265.9	Semi standard non polar	33892256
3,5-Diiodothyronine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1	3221.8	Semi standard non polar	33892256
3,5-Diiodothyronine,2TMS,isomer #2	C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)C(=O)O	3210.0	Semi standard non polar	33892256
3,5-Diiodothyronine,2TMS,isomer #3	C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C	3184.6	Semi standard non polar	33892256
3,5-Diiodothyronine,2TMS,isomer #4	C[Si](C)(C)N(C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O)[Si](C)(C)C	3357.2	Semi standard non polar	33892256
3,5-Diiodothyronine,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C	3191.5	Semi standard non polar	33892256
3,5-Diiodothyronine,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C	2850.1	Standard non polar	33892256
3,5-Diiodothyronine,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C	3105.1	Standard polar	33892256
3,5-Diiodothyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1	3352.8	Semi standard non polar	33892256
3,5-Diiodothyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1	3037.3	Standard non polar	33892256
3,5-Diiodothyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1	3284.8	Standard polar	33892256
3,5-Diiodothyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3311.9	Semi standard non polar	33892256
3,5-Diiodothyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3011.1	Standard non polar	33892256
3,5-Diiodothyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3246.9	Standard polar	33892256
3,5-Diiodothyronine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3361.2	Semi standard non polar	33892256
3,5-Diiodothyronine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3007.0	Standard non polar	33892256
3,5-Diiodothyronine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C	3019.0	Standard polar	33892256
3,5-Diiodothyronine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(N)C(=O)O)C=C2I)C=C1	3478.8	Semi standard non polar	33892256
3,5-Diiodothyronine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1	3487.6	Semi standard non polar	33892256
3,5-Diiodothyronine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O	3524.0	Semi standard non polar	33892256
3,5-Diiodothyronine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1	3725.5	Semi standard non polar	33892256
3,5-Diiodothyronine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1)C(=O)O	3735.7	Semi standard non polar	33892256
3,5-Diiodothyronine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3719.1	Semi standard non polar	33892256
3,5-Diiodothyronine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3820.5	Semi standard non polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3936.0	Semi standard non polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3523.4	Standard non polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C	3393.5	Standard polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C1	4073.5	Semi standard non polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C1	3616.3	Standard non polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2I)C=C1	3476.7	Standard polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4043.1	Semi standard non polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3617.7	Standard non polar	33892256
3,5-Diiodothyronine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3440.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5200920000-b93c897ae4b72c23519b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9600058000-453c4267903543f11c76	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodothyronine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodothyronine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-0000090000-0c32e1647fb8ad73f0b7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodothyronine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-003r-0003970000-f35e706ebe5a01fd53a0	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Diiodothyronine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0fb9-0129700000-6535af9505fe3bcdc464	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 10V, Positive-QTOF	splash10-004i-0100890000-a4c3898b3f5e77f46dbe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 20V, Positive-QTOF	splash10-004i-0000910000-e0bf5e5b19dbc8da3983	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 40V, Positive-QTOF	splash10-016u-2009200000-ed00e535f6a635c85b0f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 10V, Negative-QTOF	splash10-00di-0100090000-71fa162482707b5eb3d7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 20V, Negative-QTOF	splash10-0ab9-1600390000-2a1c97e2e04e68ad8521	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 40V, Negative-QTOF	splash10-05iu-9102200000-a695396d7ea8bb382a70	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 10V, Positive-QTOF	splash10-004i-0000290000-18b94b7e0180ef2e9c95	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 20V, Positive-QTOF	splash10-004i-0000920000-c6b727eb99ca0e5a1992	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 40V, Positive-QTOF	splash10-004i-4203900000-460478b6a64a00caf41a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 10V, Negative-QTOF	splash10-00di-0000090000-2c48801ad2bd401ad2c3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 20V, Negative-QTOF	splash10-00fr-1800290000-803aa569bbb8878983f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodothyronine 40V, Negative-QTOF	splash10-004i-0900000000-0dba40d354fa6a5575e0	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Brain

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000016 +/- 0.000006 uM	Adult (>18 years old)	Both	Normal	9141546	details
Urine	Detected and Quantified	0.000018 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3988241	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000046 +/- 0.000048 uM	Adult (>18 years old)	Both	Sepsis	9141546	details
Blood	Detected and Quantified	0.000024 +/- 0.000014 uM	Adult (>18 years old)	Both	Cirrhosis	9141546	details
Blood	Detected and Quantified	0.000021 +/- 0.000005 uM	Adult (>18 years old)	Both	Brain tumors	9141546	details
Urine	Detected and Quantified	0.000086 umol/mmol creatinine	Adult (>18 years old)	Both	Hyperthyroidism	3988241	details
Urine	Detected and Quantified	0.00001 umol/mmol creatinine	Adult (>18 years old)	Both	Hypothyroidism	3988241	details

Associated Disorders and Diseases

Disease References

Sepsis
Pinna G, Meinhold H, Hiedra L, Thoma R, Hoell T, Graf KJ, Stoltenburg-Didinger G, Eravci M, Prengel H, Brodel O, Finke R, Baumgartner A: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors. J Clin Endocrinol Metab. 1997 May;82(5):1535-42. [PubMed:9141546 ]
Cirrhosis
Pinna G, Meinhold H, Hiedra L, Thoma R, Hoell T, Graf KJ, Stoltenburg-Didinger G, Eravci M, Prengel H, Brodel O, Finke R, Baumgartner A: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors. J Clin Endocrinol Metab. 1997 May;82(5):1535-42. [PubMed:9141546 ]
Brain tumors
Pinna G, Meinhold H, Hiedra L, Thoma R, Hoell T, Graf KJ, Stoltenburg-Didinger G, Eravci M, Prengel H, Brodel O, Finke R, Baumgartner A: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors. J Clin Endocrinol Metab. 1997 May;82(5):1535-42. [PubMed:9141546 ]
Hyperthyroidism
Hommel E, Faber J, Kirkegaard C, Siersbaek-Nielsen K, Friis T: Urinary excretion of unconjugated and conjugated 3,5-diiodothyronine. Horm Metab Res. 1985 Feb;17(2):90-2. [PubMed:3988241 ]
Hypothyroidism
Hommel E, Faber J, Kirkegaard C, Siersbaek-Nielsen K, Friis T: Urinary excretion of unconjugated and conjugated 3,5-diiodothyronine. Horm Metab Res. 1985 Feb;17(2):90-2. [PubMed:3988241 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022128

KNApSAcK ID

Not Available

Chemspider ID

110252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3,5-Diiodothyronine

METLIN ID

5564

PubChem Compound

123675

PDB ID

Not Available

ChEBI ID

350682

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000193

Good Scents ID

Not Available

References

Synthesis Reference

Valashek, I. E.; Kochergin, P. M.; Vinogradova, E. M.; Budanova, L. I. Synthesis of 3,5-diiodo-DL-thyronine. Khimiko-Farmatsevticheskii Zhurnal (1995), 29(6), 44.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Goglia F: Biological effects of 3,5-diiodothyronine (T(2)). Biochemistry (Mosc). 2005 Feb;70(2):164-72. [PubMed:15807655 ]
Nishikawa M, Inada M, Naito K, Ishii H, Tanaka K, Mashio Y, Imura H: Serum concentrations of 3, 3'-diiodothyronine, 3', 5'-diiodothyronine, and 3, 5-diiodothyronine in altered thyroid states. Endocrinol Jpn. 1983 Apr;30(2):167-72. [PubMed:6641638 ]
Takeshita A: [Monoiodothyronine and diiodothyronine]. Nihon Rinsho. 1999 Dec;57 Suppl:86-9. [PubMed:10778070 ]
Pinna G, Meinhold H, Hiedra L, Thoma R, Hoell T, Graf KJ, Stoltenburg-Didinger G, Eravci M, Prengel H, Brodel O, Finke R, Baumgartner A: Elevated 3,5-diiodothyronine concentrations in the sera of patients with nonthyroidal illnesses and brain tumors. J Clin Endocrinol Metab. 1997 May;82(5):1535-42. [PubMed:9141546 ]
Martinez MB, Ruan M, Fitzpatrick LA: Altered response to thyroid hormones by breast and ovarian cancer cells. Anticancer Res. 2000 Nov-Dec;20(6B):4141-6. [PubMed:11205239 ]
Faber J, Heaf J, Kirkegaard C, Lumholtz IB, Siersbaek-Nielsen K, Kolendorf K, Friis T: Simultaneous turnover studies of thyroxine, 3,5,3' and 3,3',5'-triiodothyronine, 3,5-, 3,3'-, and 3',5'- diiodothyronine, and 3'-monoiodothyronine in chronic renal failure. J Clin Endocrinol Metab. 1983 Feb;56(2):211-7. [PubMed:6401746 ]
Kirkegaard C, Faber J, Siersbaek-Nielsen K, Friis T: A radioimmunoassay of serum 3,5-diiodothyronine. Acta Endocrinol (Copenh). 1981 Jun;97(2):196-201. [PubMed:7234287 ]
Jaedig S, Faber J: The effect of starvation and refeeding with oral versus intravenous glucose on serum 3,5-,3,3'-and 3'-5'-diiodothyronine and 3'-monoiodothyronine. Acta Endocrinol (Copenh). 1982 Jul;100(3):388-92. [PubMed:7113605 ]
Engler D, Merkelbach U, Steiger G, Burger AG: The monodeiodination of triiodothyronine and reverse triiodothyronine in man: a quantitative evaluation of the pathway by the use of turnover rate techniques. J Clin Endocrinol Metab. 1984 Jan;58(1):49-61. [PubMed:6689682 ]
Baur A, Bauer K, Jarry H, Kohrle J: 3,5-diiodo-L-thyronine stimulates type 1 5'deiodinase activity in rat anterior pituitaries in vivo and in reaggregate cultures and GH3 cells in vitro. Endocrinology. 1997 Aug;138(8):3242-8. [PubMed:9231774 ]
Engler D, Burger AG: The deiodination of the iodothyronines and of their derivatives in man. Endocr Rev. 1984 Spring;5(2):151-84. [PubMed:6376077 ]
Hommel E, Faber J, Kirkegaard C, Siersbaek-Nielsen K, Friis T: Urinary excretion of unconjugated and conjugated 3,5-diiodothyronine. Horm Metab Res. 1985 Feb;17(2):90-2. [PubMed:3988241 ]
Senese R, de Lange P, Petito G, Moreno M, Goglia F, Lanni A: 3,5-Diiodothyronine: A Novel Thyroid Hormone Metabolite and Potent Modulator of Energy Metabolism. Front Endocrinol (Lausanne). 2018 Jul 25;9:427. doi: 10.3389/fendo.2018.00427. eCollection 2018. [PubMed:30090086 ]
Antonelli A, Fallahi P, Ferrari SM, Di Domenicantonio A, Moreno M, Lanni A, Goglia F: 3,5-diiodo-L-thyronine increases resting metabolic rate and reduces body weight without undesirable side effects. J Biol Regul Homeost Agents. 2011 Oct-Dec;25(4):655-60. [PubMed:22217997 ]

Showing metabocard for 3,5-Diiodothyronine (HMDB0000582)

MOL for HMDB0000582 (3,5-Diiodothyronine)

3D MOL for HMDB0000582 (3,5-Diiodothyronine)

3D SDF for HMDB0000582 (3,5-Diiodothyronine)

3D-SDF for HMDB0000582 (3,5-Diiodothyronine)

PDB for HMDB0000582 (3,5-Diiodothyronine)

3D PDB for HMDB0000582 (3,5-Diiodothyronine)

SMILES for HMDB0000582 (3,5-Diiodothyronine)

INCHI for HMDB0000582 (3,5-Diiodothyronine)

Structure for HMDB0000582 (3,5-Diiodothyronine)

3D Structure for HMDB0000582 (3,5-Diiodothyronine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra