NP-MRD: Showing NP-Card for 3,5-Diiodothyronine (NP0000465)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:41:57 UTC

NP-MRD ID

NP0000465

Secondary Accession Numbers

None

Natural Product 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

HMDB0000582
     RDKit          3D
3,5-Diiodothyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2373    2.1553   -0.1105 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761    1.2060    0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9179    1.7199   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531    0.8377   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318   -0.1744   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3494   -0.9687   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968   -2.5383   -1.9780 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.3941   -0.7702    0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4899   -1.5684    0.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668   -1.2837    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593   -0.1735   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3634    0.1021   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3823   -0.7410   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7087   -0.4724   -0.8195 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0932   -1.8565    0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -2.1223    0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.2380    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170    0.5546    3.1099 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    1.0379    1.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5249   -0.1391   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5954   -0.2921   -0.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7660   -1.2686    0.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8081    3.1047   -0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9482    2.1618    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024    1.2688    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027    2.7540   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    1.7369   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266   -0.3316   -1.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2846    0.5142   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6040    0.9779   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3327    0.0845   -0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9039   -2.5212    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6034   -3.0181    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325    1.8208    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -2.0351   -0.6190 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>
NP0000465

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

HMDB0000582
     RDKit          3D
3,5-Diiodothyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2373    2.1553   -0.1105 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761    1.2060    0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9179    1.7199   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531    0.8377   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318   -0.1744   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3494   -0.9687   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968   -2.5383   -1.9780 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.3941   -0.7702    0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4899   -1.5684    0.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668   -1.2837    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593   -0.1735   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3634    0.1021   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3823   -0.7410   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7087   -0.4724   -0.8195 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0932   -1.8565    0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -2.1223    0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.2380    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170    0.5546    3.1099 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    1.0379    1.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5249   -0.1391   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5954   -0.2921   -0.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7660   -1.2686    0.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8081    3.1047   -0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9482    2.1618    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024    1.2688    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027    2.7540   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    1.7369   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266   -0.3316   -1.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2846    0.5142   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6040    0.9779   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3327    0.0845   -0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9039   -2.5212    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6034   -3.0181    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325    1.8208    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -2.0351   -0.6190 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

HMDB0000582
     RDKit          3D
3,5-Diiodothyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.2373    2.1553   -0.1105 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761    1.2060    0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9179    1.7199   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531    0.8377   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318   -0.1744   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3494   -0.9687   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968   -2.5383   -1.9780 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.3941   -0.7702    0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4899   -1.5684    0.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668   -1.2837    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593   -0.1735   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3634    0.1021   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3823   -0.7410   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7087   -0.4724   -0.8195 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0932   -1.8565    0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -2.1223    0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.2380    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170    0.5546    3.1099 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    1.0379    1.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5249   -0.1391   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5954   -0.2921   -0.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7660   -1.2686    0.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8081    3.1047   -0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9482    2.1618    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024    1.2688    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027    2.7540   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    1.7369   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266   -0.3316   -1.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2846    0.5142   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6040    0.9779   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3327    0.0845   -0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9039   -2.5212    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6034   -3.0181    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325    1.8208    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -2.0351   -0.6190 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 NMR Assignments

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 Mass

525.0770 Da

Monoisotopic Mass

524.89339 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000582

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
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 NP-Card for 3,5-Diiodothyronine (NP0000465)

MOL for NP0000465 (3,5-Diiodothyronine)

3D MOL for NP0000465 (3,5-Diiodothyronine)

3D SDF for NP0000465 (3,5-Diiodothyronine)

3D-SDF for NP0000465 (3,5-Diiodothyronine)

PDB for NP0000465 (3,5-Diiodothyronine)

3D PDB for NP0000465 (3,5-Diiodothyronine)

SMILES for NP0000465 (3,5-Diiodothyronine)

INCHI for NP0000465 (3,5-Diiodothyronine)

Structure for NP0000465 (3,5-Diiodothyronine)

3D Structure for NP0000465 (3,5-Diiodothyronine)