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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:20:02 UTC

HMDB ID

HMDB0000667

Secondary Accession Numbers

HMDB00667

Metabolite Identification

Common Name

L-Thyronine

Description

Thyronine (T0) is a de-iodinated form of thyroxine. Thyronine are a group of metabolites derived from thyroxine and triiodothyronine via the peripheral enzymatic removal of iodines from the thyroxine nucleus. Thyronine is the thyroxine nucleus devoid of its four iodine atoms. Thyronine (T0) has been identified in human urine. In 22 normal individuals urinary thyronine concentrations were found to range between 8-25 nmol‚ÅÑ24h (PMID: 479355 ). Thyronine is thought to be a byproduct of thyroxine metabolism and arises through the action of thyroxine deiodinases.

Structure

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

HMDB0000667
     RDKit          3D
L-Thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.1977    2.1484    0.1746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081    0.9583    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3407   -0.0263   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095   -0.4557   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435   -1.5567    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.9379    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310   -1.2210    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8051   -1.6073    0.9778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.8804    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862    0.2015    1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943    0.9142    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    0.5780   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2914    1.2954   -0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060   -0.5022   -0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992   -1.2181   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -0.1247   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.2205   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    0.3450    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.8378    2.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -0.8098    1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789    2.5384   -0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    2.8004    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9507    1.2755   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2728    0.4358   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.9171   -0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -2.1351    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -2.8044    1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    0.5154    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568    1.7598    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    2.0894   -1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -0.7569   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601   -2.0640   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    0.4323   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464    1.0797   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -1.4082    0.6328 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  2  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 17  4  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
M  END

L-Thyronine.mol
  Mrv1652305271900192D          

 20 21  0  0  0  0            999 V2000
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
  5 18  1  0  0  0  0
  1 19  2  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000667

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO4/c16-14(15(18)19)9-10-1-5-12(6-2-10)20-13-7-3-11(17)4-8-13/h1-8,14,17H,9,16H2,(H,18,19)/t14-/m0/s1

> <INCHI_KEY>
KKCIOUWDFWQUBT-AWEZNQCLSA-N

> <FORMULA>
C15H15NO4

> <MOLECULAR_WEIGHT>
273.2839

> <EXACT_MASS>
273.100107973

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.720858323594932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
0.011688075180960931

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.895019385843883

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6067971044923706

> <JCHEM_PKA_STRONGEST_BASIC>
9.261323301384072

> <JCHEM_POLAR_SURFACE_AREA>
92.78000000000002

> <JCHEM_REFRACTIVITY>
73.33800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thyronine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000667
     RDKit          3D
L-Thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.1977    2.1484    0.1746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081    0.9583    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3407   -0.0263   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095   -0.4557   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435   -1.5567    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.9379    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310   -1.2210    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8051   -1.6073    0.9778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.8804    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862    0.2015    1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943    0.9142    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    0.5780   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2914    1.2954   -0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060   -0.5022   -0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992   -1.2181   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -0.1247   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.2205   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    0.3450    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.8378    2.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -0.8098    1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789    2.5384   -0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    2.8004    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9507    1.2755   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2728    0.4358   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.9171   -0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -2.1351    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -2.8044    1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    0.5154    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568    1.7598    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    2.0894   -1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -0.7569   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601   -2.0640   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    0.4323   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464    1.0797   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -1.4082    0.6328 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  2  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 17  4  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: L-Thyronine.mol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       5.335   0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.668  -1.540   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.668  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   1.540   0.000  0.00  0.00           O+0
CONECT    1    3   19   20                                                  
CONECT    2    3                                                            
CONECT    3    2    1    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
CONECT   17    8   18                                                       
CONECT   18   17    5                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0000667
HETATM    1  N1  UNL     1      -3.198   2.148   0.175  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.008   0.958   0.026  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.341  -0.026  -0.896  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.010  -0.456  -0.396  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.843  -1.557   0.436  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.593  -1.938   0.889  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.531  -1.221   0.518  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.805  -1.607   0.978  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.904  -0.880   0.596  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.386   0.202   1.307  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.494   0.914   0.898  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.168   0.578  -0.236  1.00  0.00           C  
HETATM   13  O2  UNL     1       6.291   1.295  -0.657  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.706  -0.502  -0.968  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.599  -1.218  -0.565  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.395  -0.125  -0.307  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.855   0.221  -0.733  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.260   0.345   1.329  1.00  0.00           C  
HETATM   19  O3  UNL     1      -3.804   0.838   2.393  1.00  0.00           O  
HETATM   20  O4  UNL     1      -5.019  -0.810   1.418  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.879   2.538  -0.716  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.587   2.800   0.857  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.951   1.276  -0.465  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.273   0.436  -1.906  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.991  -0.917  -0.999  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.706  -2.135   0.741  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.471  -2.804   1.542  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.892   0.515   2.216  1.00  0.00           H  
HETATM   29  H9  UNL     1       4.857   1.760   1.470  1.00  0.00           H  
HETATM   30  H10 UNL     1       6.120   2.089  -1.280  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.249  -0.757  -1.865  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.260  -2.064  -1.163  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.298   0.432  -0.591  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.946   1.080  -1.377  1.00  0.00           H  
HETATM   35  H15 UNL     1      -5.222  -1.408   0.633  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3   18   23
CONECT    3    4   24   25
CONECT    4    5    5   17
CONECT    5    6   26
CONECT    6    7    7   27
CONECT    7    8   16
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   14
CONECT   13   30
CONECT   14   15   15   31
CONECT   15   32
CONECT   16   17   17   33
CONECT   17   34
CONECT   18   19   19   20
CONECT   20   35
END

HMDB0000667
     RDKit          3D
L-Thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.1977    2.1484    0.1746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081    0.9583    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3407   -0.0263   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095   -0.4557   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435   -1.5567    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.9379    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310   -1.2210    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8051   -1.6073    0.9778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.8804    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862    0.2015    1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943    0.9142    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    0.5780   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2914    1.2954   -0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060   -0.5022   -0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992   -1.2181   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -0.1247   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.2205   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    0.3450    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.8378    2.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -0.8098    1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789    2.5384   -0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    2.8004    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9507    1.2755   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2728    0.4358   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.9171   -0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -2.1351    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -2.8044    1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    0.5154    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568    1.7598    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    2.0894   -1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -0.7569   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601   -2.0640   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    0.4323   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464    1.0797   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -1.4082    0.6328 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  2  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 17  4  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(4-Hydroxyphenoxy)-L-phenylalanine	ChEBI
O-(4-Hydroxyphenyl)-L-tyrosine	ChEBI
b-(p-Hydroxyphenoxy)phenylalanine	HMDB
beta-(p-Hydroxyphenoxy)phenylalanine	HMDB
Desiodothyroxine	HMDB
O-(4-Hydroxyphenyl)tyrosine	HMDB
Thyronine	HMDB
Thyronines	HMDB

Chemical Formula

C₁₅H₁₅NO₄

Average Molecular Weight

273.2839

Monoisotopic Molecular Weight

273.100107973

IUPAC Name

(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid

Traditional Name

thyronine

CAS Registry Number

1596-67-4

SMILES

N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O

InChI Identifier

InChI=1S/C15H15NO4/c16-14(15(18)19)9-10-1-5-12(6-2-10)20-13-7-3-11(17)4-8-13/h1-8,14,17H,9,16H2,(H,18,19)/t14-/m0/s1

InChI Key

KKCIOUWDFWQUBT-AWEZNQCLSA-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
Amphetamine or derivatives
Alpha-amino acid
L-alpha-amino acid
Phenol ether
Phenoxy compound
Aralkylamine
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Amine
Organic oxide
Primary amine
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

thyronine (CHEBI:30662 )

Ontology

Physiological effect

Health effect

Hyperthyroidism (HMDB: HMDB0000667)
Amyotrophic lateral sclerosis (HMDB: HMDB0000667)

Renal system and urinary system

Renal disorder

Chronic kidney disease (HMDB: HMDB0000667)

Disposition

Biological location

Biofluid or Excreta

Blood (HMDB: HMDB0000667)
Urine (HMDB: HMDB0000667)

Organ

Gland

Endocrine gland

Thyroid gland (HMDB: HMDB0000667)

Thyroid Gland (HMDB: HMDB0000667)

Spleen (HMDB: HMDB0000667)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2915230)

Excreta

Biofluid or Excreta

Urine (PMID: 3410934)

Cellular substructure

Cytoplasm (HMDB: HMDB0000667)

Source

Endogenous

Endogenous (HMDB: HMDB0000667)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	255 °C	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	0.05 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	0.012	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	1.61	ChemAxon
pKa (Strongest Basic)	9.26	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	73.34 m³·mol⁻¹	ChemAxon
Polarizability	27.72 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
DarkChem	[M+H]+	166.219	31661259
DarkChem	[M-H]-	164.91	31661259
AllCCS	[M+H]+	163.417	32859911
AllCCS	[M-H]-	165.683	32859911
DeepCCS	[M+H]+	162.89	30932474
DeepCCS	[M-H]-	160.532	30932474
DeepCCS	[M-2H]-	193.418	30932474
DeepCCS	[M+Na]+	168.983	30932474
AllCCS	[M+H]+	163.4	32859911
AllCCS	[M+H-H2O]+	159.9	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	165.7	32859911
AllCCS	[M+Na-2H]-	165.4	32859911
AllCCS	[M+HCOO]-	165.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Thyronine	N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O	4236.7	Standard polar	33892256
L-Thyronine	N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O	2629.7	Standard non polar	33892256
L-Thyronine	N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O	2752.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Thyronine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(OC2=CC=C(C[C@H](N)C(=O)O)C=C2)C=C1	2699.2	Semi standard non polar	33892256
L-Thyronine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OC2=CC=C(O)C=C2)C=C1	2671.0	Semi standard non polar	33892256
L-Thyronine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(=O)O	2749.8	Semi standard non polar	33892256
L-Thyronine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C=C1	2640.6	Semi standard non polar	33892256
L-Thyronine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C=C1)C(=O)O	2697.4	Semi standard non polar	33892256
L-Thyronine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(=O)O[Si](C)(C)C	2675.1	Semi standard non polar	33892256
L-Thyronine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(=O)O)[Si](C)(C)C	2889.4	Semi standard non polar	33892256
L-Thyronine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C=C1)C(=O)O[Si](C)(C)C	2639.6	Semi standard non polar	33892256
L-Thyronine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C=C1)C(=O)O[Si](C)(C)C	2512.7	Standard non polar	33892256
L-Thyronine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C=C1)C(=O)O[Si](C)(C)C	3000.8	Standard polar	33892256
L-Thyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	2821.0	Semi standard non polar	33892256
L-Thyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	2620.7	Standard non polar	33892256
L-Thyronine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(OC2=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	3124.3	Standard polar	33892256
L-Thyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2802.1	Semi standard non polar	33892256
L-Thyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2637.7	Standard non polar	33892256
L-Thyronine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	3095.9	Standard polar	33892256
L-Thyronine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2805.5	Semi standard non polar	33892256
L-Thyronine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2598.3	Standard non polar	33892256
L-Thyronine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C)C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2897.7	Standard polar	33892256
L-Thyronine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(C[C@H](N)C(=O)O)C=C2)C=C1	2978.5	Semi standard non polar	33892256
L-Thyronine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OC2=CC=C(O)C=C2)C=C1	2945.1	Semi standard non polar	33892256
L-Thyronine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(=O)O	3008.7	Semi standard non polar	33892256
L-Thyronine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1	3187.7	Semi standard non polar	33892256
L-Thyronine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1)C(=O)O	3268.7	Semi standard non polar	33892256
L-Thyronine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3205.6	Semi standard non polar	33892256
L-Thyronine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3376.9	Semi standard non polar	33892256
L-Thyronine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3386.5	Semi standard non polar	33892256
L-Thyronine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3115.7	Standard non polar	33892256
L-Thyronine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3280.6	Standard polar	33892256
L-Thyronine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3599.3	Semi standard non polar	33892256
L-Thyronine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3176.4	Standard non polar	33892256
L-Thyronine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3328.2	Standard polar	33892256
L-Thyronine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3544.0	Semi standard non polar	33892256
L-Thyronine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3194.3	Standard non polar	33892256
L-Thyronine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3297.4	Standard polar	33892256
L-Thyronine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3755.5	Semi standard non polar	33892256
L-Thyronine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3328.7	Standard non polar	33892256
L-Thyronine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3223.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-8890000000-063f8216e411912c2cf5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-5329100000-f43bd1463108b6a840a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Thyronine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Thyronine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0adi-0090000000-0c68e00d57e7915b5486	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Thyronine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014i-2950000000-eb4bb2399809067f70a6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Thyronine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014l-6900000000-9a61d9007b69a8a69798	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 10V, Positive-QTOF	splash10-05di-0090000000-f5a6acd9aacd1337d8ef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 20V, Positive-QTOF	splash10-004i-0290000000-04f1d4a27147d2e5de3e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 40V, Positive-QTOF	splash10-014i-8910000000-485f22cea6f55f284b41	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 10V, Negative-QTOF	splash10-00di-0090000000-91792b99e52e68749b3d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 20V, Negative-QTOF	splash10-05fr-1290000000-447661ac05f8a8443c16	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 40V, Negative-QTOF	splash10-0a4i-9800000000-b0151cc80b1606bc9792	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 10V, Positive-QTOF	splash10-00b9-0090000000-9aca8f320542aca6d6d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 20V, Positive-QTOF	splash10-056r-0090000000-38d269a3c5b4c5a4aa48	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 40V, Positive-QTOF	splash10-006x-4940000000-bf911509debb14b7a5f2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 10V, Negative-QTOF	splash10-05fr-0090000000-9126d4805898c988e8b9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 20V, Negative-QTOF	splash10-0c00-2390000000-1b269790c138ee1f270f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Thyronine 40V, Negative-QTOF	splash10-05fr-5930000000-a276644672d767ec29e5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Spleen
Thyroid Gland

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.29 +/- 0.084 uM	Adult (>18 years old)	Both	Normal	2915230	details
Urine	Detected and Quantified	0.0038 +/- 0.00048 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3410934	details
Urine	Detected and Quantified	0.0010 +/- 0.00038 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3098453	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.34 +/- 0.02 uM	Adult (>18 years old)	Both	Amyotrophic lateral sclerosis	2915230	details
Urine	Detected and Quantified	0.0069 +/- 0.0014 umol/mmol creatinine	Adult (>18 years old)	Both	Hyperthyroidism	3410934	details
Urine	Detected and Quantified	0.00028 +/- 0.00017 umol/mmol creatinine	Adult (>18 years old)	Both	Chronic renal disease	3098453	details

Associated Disorders and Diseases

Disease References

Amyotrophic lateral sclerosis
Malin JP, Kodding R, Fuhrmann H, von zur Muhlen A: T4, T3 and rT3 levels in serum and cerebrospinal fluid of patients with amyotrophic lateral sclerosis. J Neurol. 1989 Jan;236(1):57-9. [PubMed:2915230 ]
Hyperthyroidism
Chopra IJ, Boado RJ, Geffner DL, Solomon DH: A radioimmunoassay for measurement of thyronine and its acetic acid analog in urine. J Clin Endocrinol Metab. 1988 Sep;67(3):480-7. [PubMed:3410934 ]
Chronic kidney disease
Ramsden DB, Farmer M, Mohammed MN, McGonigle RS, Sheppard MC: 3,5-Diiodotyrosine and thyronine in the urine of patients with chronic renal disease. Clin Endocrinol (Oxf). 1986 May;24(5):491-5. [PubMed:3098453 ]

Associated OMIM IDs

105400 (Amyotrophic lateral sclerosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022172

KNApSAcK ID

Not Available

Chemspider ID

4574450

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thyronine

METLIN ID

5637

PubChem Compound

5461103

PDB ID

Not Available

ChEBI ID

30662

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Harrington, C. R.; Rivers, Rosalind V. Pitt. New synthesis of thyronine. Journal of the Chemical Society (1940), 1101-3.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Chopra IJ, Wu SY, Teco GN, Santini F: A radioimmunoassay for measurement of 3,5,3'-triiodothyronine sulfate: studies in thyroidal and nonthyroidal diseases, pregnancy, and neonatal life. J Clin Endocrinol Metab. 1992 Jul;75(1):189-94. [PubMed:1619009 ]
Malin JP, Kodding R, Fuhrmann H, von zur Muhlen A: T4, T3 and rT3 levels in serum and cerebrospinal fluid of patients with amyotrophic lateral sclerosis. J Neurol. 1989 Jan;236(1):57-9. [PubMed:2915230 ]
Lomo LC, Zhang F, McCormick DJ, Giraldo AA, David CS, Kong YC: Flexibility of the thyroiditogenic T cell repertoire for murine autoimmune thyroiditis in CD8-deficient (beta2m -/-) and T cell receptor Vbeta(c) congenic mice. Autoimmunity. 1998;27(3):127-33. [PubMed:9609129 ]
LoPresti JS, Anderson KP, Nicoloff JT: Does a hidden pool of reverse triiodothyronine (rT3) production contribute to total thyroxine (T4) disposal in high T4 states in man. J Clin Endocrinol Metab. 1990 May;70(5):1479-84. [PubMed:2335581 ]
Ramsden DB, Farmer M, Mohammed MN, Willetts P: Mass spectral properties of volatile derivatives of thyronine (T0) and use of these in the study of thyronine excretion in eu-, hyper- and hypothyroidism. Biomed Mass Spectrom. 1984 Apr;11(4):193-8. [PubMed:6733255 ]
Morell M, Fernandez-Guillien FJ, Lopez-Garcia JM: Levels of L-T3 in maternal and foetal compartments following experimental modifications of the maternal thyroid state in rats. Arch Int Physiol Biochim Biophys. 1994 Jan-Feb;102(1):1-3. [PubMed:7516725 ]
Kohrle J: The deiodinase family: selenoenzymes regulating thyroid hormone availability and action. Cell Mol Life Sci. 2000 Dec;57(13-14):1853-63. [PubMed:11215512 ]
Willetts P, Crossley DN, Ramsden DB, Hoffenberg R: The role of thyronine in thyroid hormone metabolism. J Clin Endocrinol Metab. 1979 Oct;49(4):658-60. doi: 10.1210/jcem-49-4-658. [PubMed:479355 ]

Showing metabocard for L-Thyronine (HMDB0000667)

MOL for HMDB0000667 (L-Thyronine)

3D MOL for HMDB0000667 (L-Thyronine)

3D SDF for HMDB0000667 (L-Thyronine)

3D-SDF for HMDB0000667 (L-Thyronine)

PDB for HMDB0000667 (L-Thyronine)

3D PDB for HMDB0000667 (L-Thyronine)

SMILES for HMDB0000667 (L-Thyronine)

INCHI for HMDB0000667 (L-Thyronine)

Structure for HMDB0000667 (L-Thyronine)

3D Structure for HMDB0000667 (L-Thyronine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra