MiMeDB: Showing metabocard for Thyroxine (MMDBc0000337)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:35:39 UTC

Update Date

2024-04-30 19:31:51 UTC

Metabolite ID

MMDBc0000337

Metabolite Identification

Common Name

Thyroxine

Description

Thyroxine (3,5,3‚Ä≤,5‚Ä≤-tetraiodothyronine) or T4 is one of two major hormones derived from the thyroid gland, the other being triiodothyronine (T3). The major form of thyroid hormone in the blood is thyroxine (T4), which has a longer half-life than T3. In humans, the ratio of T4 to T3 released into the blood is approximately 14:1. T4 is converted to the active T3 (three to four times more potent than T4) within cells by enzymes known as deiodinases (5‚Ä≤-iodinase). Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Iodine is critical to the synthesis of thyroxine and other thyroid hormones. Through a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues found in the thyroglobulin protein, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one molecule of MIT and one molecule of DIT produces triiodothyronine. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles where thyroxine is produced. If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in a condition called goitre. More specifically, the lack of thyroid hormones will lead to decreased negative feedback on the pituitary gland, leading to increased production of thyroid-stimulating hormone, which causes the thyroid to enlarge, leading to goitre. Thyroxine can be peripherally de-iodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism. Thyroid hormones function via a well-studied set of nuclear receptors, termed the thyroid hormone receptors. They act on nearly every cell in the body. In particular, thyroid hormones act to increase the basal metabolic rate, affect protein synthesis, help regulate long bone growth (synergy with growth hormone) and neural maturation, and increase the body's sensitivity to catecholamines (such as adrenaline) by permissiveness. The thyroid hormones are essential to proper development and differentiation of all cells of the human body. These hormones also regulate protein, fat, and carbohydrate metabolism, affecting how human cells use energetic compounds. They also stimulate vitamin metabolism. Numerous physiological and pathological stimuli influence thyroid hormone synthesis. Levothyroxine, a manufactured form of thyroxine, was the most prescribed medication in the United States with more than 114 million prescriptions.

Structure

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

HMDB0000248
     RDKit          3D
Thyroxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.2295   -0.3950    1.7635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    0.5456    0.7809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4197    0.0702   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995   -0.1748   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    0.8388   -1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    0.6654   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392    2.2834   -2.4092 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020   -0.5773   -1.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554   -0.6968   -1.7488 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483   -0.4465   -0.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6768   -0.0652    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6455    0.1915    1.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    0.7722    3.3353 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.9569    0.0504    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9408    0.3038    1.9766 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -0.3321   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3669   -0.5325   -0.7500 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554   -0.5836   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -1.6100   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -3.4752   -0.6593 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4103   -1.4000   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1066    0.8049    0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7654    0.2309    1.7978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7232    1.6845    0.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -0.2544    2.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5379   -1.3601    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1037    1.4905    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    0.8662   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0578   -0.8276   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6469    1.8149   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    0.0332    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7262    0.5864    2.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6480   -0.8827   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9848   -2.2205   -0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4087    2.6014   -0.1666 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  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  8 19  1  0
 19 20  1  0
 19 21  2  0
  2 22  1  0
 22 23  2  0
 22 24  1  0
 21  4  1  0
 18 10  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  3 29  1  0
  5 30  1  0
 11 31  1  0
 15 32  1  0
 18 33  1  0
 21 34  1  0
 24 35  1  0
M  END


  Mrv1652304202019192D          

 24 25  0  0  0  0            999 V2000
 9998.918510000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.060610000.8250    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4895 9998.3499    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0606 9999.1749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9185 9999.1749    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
10000.349010001.6500    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
10001.7763 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4900 9999.5885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.2057 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9193 9999.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.2057 9998.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.490010000.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.204010000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.489610000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.775010000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7750 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4895 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2040 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.062710000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.348310000.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.633710000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6337 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3482 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0627 9999.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 19  1  0  0  0  0
  1 21  1  0  0  0  0
 22  5  1  0  0  0  0
 24  7  1  0  0  0  0
 20  6  1  0  0  0  0
  1 13  1  0  0  0  0
 15  2  1  0  0  0  0
 16  4  1  0  0  0  0
 17  3  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000337

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1

> <INCHI_KEY>
XUIIKFGFIJCVMT-LBPRGKRZSA-N

> <FORMULA>
C15H11I4NO4

> <MOLECULAR_WEIGHT>
776.87

> <EXACT_MASS>
776.686681525

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
49.401554616111895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
3.7273070498224867

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.426761076989792

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.2734558653923598

> <JCHEM_PKA_STRONGEST_BASIC>
9.433364269995794

> <JCHEM_POLAR_SURFACE_AREA>
92.78

> <JCHEM_REFRACTIVITY>
126.78799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
levothyroxine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000248
     RDKit          3D
Thyroxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.2295   -0.3950    1.7635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    0.5456    0.7809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4197    0.0702   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995   -0.1748   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    0.8388   -1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    0.6654   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392    2.2834   -2.4092 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020   -0.5773   -1.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554   -0.6968   -1.7488 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483   -0.4465   -0.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6768   -0.0652    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6455    0.1915    1.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    0.7722    3.3353 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.9569    0.0504    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9408    0.3038    1.9766 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -0.3321   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3669   -0.5325   -0.7500 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554   -0.5836   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -1.6100   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -3.4752   -0.6593 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4103   -1.4000   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1066    0.8049    0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7654    0.2309    1.7978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7232    1.6845    0.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -0.2544    2.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5379   -1.3601    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1037    1.4905    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    0.8662   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0578   -0.8276   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6469    1.8149   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    0.0332    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7262    0.5864    2.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6480   -0.8827   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9848   -2.2205   -0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4087    2.6014   -0.1666 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  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  8 19  1  0
 19 20  1  0
 19 21  2  0
  2 22  1  0
 22 23  2  0
 22 24  1  0
 21  4  1  0
 18 10  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  3 29  1  0
  5 30  1  0
 11 31  1  0
 15 32  1  0
 18 33  1  0
 21 34  1  0
 24 35  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0    8664.6488668.207   0.000  0.00  0.00           O+0
HETATM    2  I   UNK     0    8659.3138668.207   0.000  0.00  0.00           I+0
HETATM    3  I   UNK     0    8661.9808663.586   0.000  0.00  0.00           I+0
HETATM    4  O   UNK     0    8659.3138665.126   0.000  0.00  0.00           O+0
HETATM    5  I   UNK     0    8664.6488665.126   0.000  0.00  0.00           I+0
HETATM    6  I   UNK     0    8667.3188669.747   0.000  0.00  0.00           I+0
HETATM    7  C   UNK     0    8669.9828665.126   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.3158665.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8672.6518665.126   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8673.9838665.899   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8672.6518663.586   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    8671.3158667.437   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8663.3148667.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.9818668.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.6478667.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.6478665.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8661.9808665.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3148665.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.6508667.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.3178668.207   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.9838667.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8665.9838665.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3178665.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.6508665.897   0.000  0.00  0.00           C+0
CONECT    1   21   13                                                       
CONECT    2   15                                                            
CONECT    3   17                                                            
CONECT    4   16                                                            
CONECT    5   22                                                            
CONECT    6   20                                                            
CONECT    7    8   24                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13   14   18    1                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16    2                                                  
CONECT   16   15   17    4                                                  
CONECT   17   16   18    3                                                  
CONECT   18   17   13                                                       
CONECT   19   20   24                                                       
CONECT   20   19   21    6                                                  
CONECT   21   20   22    1                                                  
CONECT   22   21   23    5                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19    7                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0000248
HETATM    1  N1  UNL     1      -3.229  -0.395   1.764  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.665   0.546   0.781  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.420   0.070  -0.641  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.999  -0.175  -0.915  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.205   0.839  -1.400  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.134   0.665  -1.675  1.00  0.00           C  
HETATM    7  I1  UNL     1       1.239   2.283  -2.409  1.00  0.00           I  
HETATM    8  C6  UNL     1       0.702  -0.577  -1.455  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.055  -0.697  -1.749  1.00  0.00           O  
HETATM   10  C7  UNL     1       3.048  -0.447  -0.815  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.677  -0.065   0.451  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.646   0.191   1.404  1.00  0.00           C  
HETATM   13  I2  UNL     1       3.107   0.772   3.335  1.00  0.00           I  
HETATM   14  C10 UNL     1       4.957   0.050   1.033  1.00  0.00           C  
HETATM   15  O2  UNL     1       5.941   0.304   1.977  1.00  0.00           O  
HETATM   16  C11 UNL     1       5.337  -0.332  -0.236  1.00  0.00           C  
HETATM   17  I3  UNL     1       7.367  -0.533  -0.750  1.00  0.00           I  
HETATM   18  C12 UNL     1       4.355  -0.584  -1.173  1.00  0.00           C  
HETATM   19  C13 UNL     1      -0.053  -1.610  -0.974  1.00  0.00           C  
HETATM   20  I4  UNL     1       0.864  -3.475  -0.659  1.00  0.00           I  
HETATM   21  C14 UNL     1      -1.410  -1.400  -0.705  1.00  0.00           C  
HETATM   22  C15 UNL     1      -5.107   0.805   0.915  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.765   0.231   1.798  1.00  0.00           O  
HETATM   24  O4  UNL     1      -5.723   1.685   0.060  1.00  0.00           O  
HETATM   25  H1  UNL     1      -2.267  -0.254   2.090  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.538  -1.360   1.632  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.104   1.490   0.945  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.839   0.866  -1.301  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.058  -0.828  -0.819  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.647   1.815  -1.574  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.619   0.033   0.698  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.726   0.586   2.920  1.00  0.00           H  
HETATM   33  H9  UNL     1       4.648  -0.883  -2.167  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.985  -2.220  -0.329  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.409   2.601  -0.167  1.00  0.00           H  
CONECT    1    2   25   26
CONECT    2    3   22   27
CONECT    3    4   28   29
CONECT    4    5    5   21
CONECT    5    6   30
CONECT    6    7    8    8
CONECT    8    9   19
CONECT    9   10
CONECT   10   11   11   18
CONECT   11   12   31
CONECT   12   13   14   14
CONECT   14   15   16
CONECT   15   32
CONECT   16   17   18   18
CONECT   18   33
CONECT   19   20   21   21
CONECT   21   34
CONECT   22   23   23   24
CONECT   24   35
END

HMDB0000248
     RDKit          3D
Thyroxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.2295   -0.3950    1.7635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    0.5456    0.7809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4197    0.0702   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995   -0.1748   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    0.8388   -1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    0.6654   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392    2.2834   -2.4092 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020   -0.5773   -1.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554   -0.6968   -1.7488 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483   -0.4465   -0.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6768   -0.0652    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6455    0.1915    1.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    0.7722    3.3353 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.9569    0.0504    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9408    0.3038    1.9766 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -0.3321   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3669   -0.5325   -0.7500 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554   -0.5836   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -1.6100   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -3.4752   -0.6593 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4103   -1.4000   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1066    0.8049    0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7654    0.2309    1.7978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7232    1.6845    0.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -0.2544    2.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5379   -1.3601    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1037    1.4905    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    0.8662   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0578   -0.8276   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6469    1.8149   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    0.0332    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7262    0.5864    2.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6480   -0.8827   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9848   -2.2205   -0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4087    2.6014   -0.1666 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  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  8 19  1  0
 19 20  1  0
 19 21  2  0
  2 22  1  0
 22 23  2  0
 22 24  1  0
 21  4  1  0
 18 10  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  3 29  1  0
  5 30  1  0
 11 31  1  0
 15 32  1  0
 18 33  1  0
 21 34  1  0
 24 35  1  0
M  END

Synonyms

Value	Source
3,3',5,5'-Tetraiodo-L-thyronine	ChEBI
3,5,3',5'-TETRAIODO-L-thyronine	ChEBI
4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine	ChEBI
L-T4	ChEBI
Levothyroxin	ChEBI
Levothyroxine	ChEBI
LT4	ChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine	ChEBI
T4	ChEBI
L-Thyroxine	Kegg
O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine	Kegg
3,5,3'5'-Tetraiodo-L-thyronine	Kegg
Forthyron	Kegg
(-)-Thyroxine	HMDB
3,3',5,5''-tetraiodo-L-Thyronine	HMDB
3,5,3',5'-Tetraiodothyronine	HMDB, MeSH
D-Thyroxine	HMDB
DL-Thyroxin	HMDB
Henning	HMDB
L-3,5,3',5'-Tetraiodothyronine	HMDB, MeSH
L-Thyroxin	HMDB
Laevothyroxinum	HMDB
Levothroid	HMDB, MeSH
Levothyroxine sodium	HMDB, MeSH
Levothyroxinum	HMDB
Levoxyl	HMDB, MeSH
Prestwick_548	HMDB
Synthroid	HMDB, MeSH
Tetraiodothyronine	HMDB
Tetramet	HMDB
THX	HMDB
Thyratabs	HMDB
Thyrax	HMDB, MeSH
Thyreoideum	HMDB
Thyroxin	HMDB, MeSH
Thyroxinal	HMDB
Thyroxine I 125	HMDB
Thyroxine iodine	HMDB
Allphar brand OF levothyroxine sodium	MeSH, HMDB
Berlthyrox	MeSH, HMDB
Delalande, levothyroxin	MeSH, HMDB
Dexnon	MeSH, HMDB
Eferox	MeSH, HMDB
Eltroxin	MeSH, HMDB
Kern brand OF levothyroxine sodium	MeSH, HMDB
L-Thyrox	MeSH, HMDB
L-Thyroxin henning	MeSH, HMDB
L-Thyroxin beta	MeSH, HMDB
L-Thyroxine roche	MeSH, HMDB
Levothyroxin deladande	MeSH, HMDB
Lévothyrox	MeSH, HMDB
Merck lipha santé brand OF levothyroxine sodium	MeSH, HMDB
Nourypharma brand OF levothyroxine sodium	MeSH, HMDB
Oroxine	MeSH, HMDB
Aventis brand OF levothyroxine sodium	MeSH, HMDB
Euthyrox	MeSH, HMDB
Eutirox	MeSH, HMDB
Forest brand OF levothyroxine sodium	MeSH, HMDB
Genpharm brand OF levothyroxine sodium	MeSH, HMDB
GlaxoSmithKline brand OF levothyroxine sodium	MeSH, HMDB
Goldshield brand OF levothyroxine sodium	MeSH, HMDB
LThyroxin henning	MeSH, HMDB
levo-T	MeSH, HMDB
Sanofi synthelabo brand OF levothyroxine sodium	MeSH, HMDB
Sigma brand OF levothyroxine sodium	MeSH, HMDB
Synthrox	MeSH, HMDB
Thevier	MeSH, HMDB
Watson brand OF levothyroxine sodium	MeSH, HMDB
Berlin chemie brand OF levothyroxine sodium	MeSH, HMDB
Delalande brand OF levothyroxine sodium	MeSH, HMDB
Eltroxine	MeSH, HMDB
Hexal brand 2 OF levothyroxine sodium	MeSH, HMDB
L Thyroxine roche	MeSH, HMDB
Novothyral	MeSH, HMDB
Tiroidine	MeSH, HMDB
Vortex brand OF levothyroxine sodium	MeSH, HMDB
Abbot brand OF levothyroxine sodium	MeSH, HMDB
Berlin-chemie brand OF levothyroxine sodium	MeSH, HMDB
Byk brand OF levothyroxine sodium	MeSH, HMDB
Deladande, levothyroxin	MeSH, HMDB
GlaxoWellcome brand OF levothyroxine sodium	MeSH, HMDB
Henning berlin brand OF levothyroxine sodium	MeSH, HMDB
Hexal brand 1 OF levothyroxine sodium	MeSH, HMDB
L Thyrox	MeSH, HMDB
L Thyroxin henning	MeSH, HMDB
L Thyroxin beta	MeSH, HMDB
L Thyroxine	MeSH, HMDB
LThyroxin beta	MeSH, HMDB
leo, Tiroxina	MeSH, HMDB
levo T	MeSH, HMDB
LevoT	MeSH, HMDB
Levothyroid	MeSH, HMDB
Levothyroxin delalande	MeSH, HMDB
Levoxine	MeSH, HMDB
Merck brand OF levothyroxine sodium	MeSH, HMDB
Monarch brand OF levothyroxine sodium	MeSH, HMDB
Mova brand OF levothyroxine sodium	MeSH, HMDB
Novothyrox	MeSH, HMDB
O-(4-Hydroxy-3,5-diiodophenyl) 3,5-diiodo-L-tyrosine	MeSH, HMDB
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine	MeSH, HMDB
Roche brand OF levothyroxine sodium	MeSH, HMDB
Rudefsa brand OF levothyroxine sodium	MeSH, HMDB
Sodium levothyroxine	MeSH, HMDB
T4 Thyroid hormone	MeSH, HMDB
Thyroid hormone, T4	MeSH, HMDB
Tiroxina leo	MeSH, HMDB
Unithroid	MeSH, HMDB
Betapharm brand OF levothyroxine sodium	MeSH, HMDB

Molecular Formula

C₁₅H₁₁I₄NO₄

Average Mass

776.87

Monoisotopic Mass

776.686681525

IUPAC Name

(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid

Traditional Name

levothyroxine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1

InChI Key

XUIIKFGFIJCVMT-LBPRGKRZSA-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
L-alpha-amino acid
Phenoxy compound
Phenol ether
2-halophenol
2-iodophenol
Aralkylamine
Phenol
Halobenzene
Iodobenzene
Aryl halide
Aryl iodide
Benzenoid
Monocyclic benzene moiety
Amino acid
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organoiodide
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Primary amine
Amine
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:18332 )
L-phenylalanine derivative (CHEBI:18332 )
iodophenol (CHEBI:18332 )
2-halophenol (CHEBI:18332 )
thyroxine (CHEBI:18332 )
thyroxine (C01829 )
Other amino acids (C01829 )
Biogenic amines (C01829 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	1.15	ALOGPS
logP	3.73	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	0.27	ChemAxon
pKa (Strongest Basic)	9.43	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	126.79 m³·mol⁻¹	ChemAxon
Polarizability	49.4 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-4002002900-0d489fed1cb888a2d9d0	2017-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0ac9-0591664310-c9b7aec3184ebb20a2da	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-2566449540-35bb942c7bcbcfe41af7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00xr-3375497520-9dee3cb0c153e6c6df9e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0059-0001001900-83ff4aafed0b73c6c7b7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0900000000-6e0a640216afcce0837e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-004i-0900000000-9223d3d63e3db43052a7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-004i-0900000000-1e8e674422aa4d820da7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0132219000-42259b5a596f74aec76f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0019217000-baafc92556cb18d71b3a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-0900000000-bb154453510a75ca822c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-004i-0900000000-f785346765de92765afd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000119000-af7b1e923ec5750514af	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0f8j-1248309000-68eea5695ceb400ea5b0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0029337000-a85b59c3575dc95d36fd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0003109000-480d647f8d49feeec28c	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01si-0000000900-524d052a32c1fe4b904d	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000001900-553f6a4045ef2241fd85	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0009000000-d2431d885a79bb80b7a5	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-137b5f8f48031bc9aa4f	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-0004001900-db1d8cdb93785d786382	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0h9u-7029014300-3bd9620b0c6a8dd20c93	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000900-95266ab7e52b7d3cb322	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1700000900-195c16ab7434b857e712	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-0dba40d354fa6a5575e0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000900-d76aec17d3d890cb64c1	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Feces
Fibroblasts
Intestine
Neuron
Ovary
Placenta
Platelet
Prostate
Saliva
Skeletal Muscle
Spleen
Testis
Thyroid Gland
Urine

Tissue Locations

Adipose Tissue
Fibroblasts
Intestine
Neuron
Ovary
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Testis
Thyroid Gland

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191946	Thyroid peroxidase	Unknown	P07202	Homo sapiens
MMDBp0192113	Solute carrier organic anion transporter family member 1C1	Transporter	Q9NYB5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0192670	Type I iodothyronine deiodinase	Enzyme	P49895	Homo sapiens
MMDBp0192671	Type II iodothyronine deiodinase	Enzyme	Q92813	Homo sapiens
MMDBp0193289	Transthyretin	Enzyme	P02766	Homo sapiens
MMDBp0193712	Thyroxine-binding globulin	Enzyme	P05543	Homo sapiens
MMDBp0193808	4F2 cell-surface antigen heavy chain	Unknown	P08195	Homo sapiens
MMDBp0196040	Type III iodothyronine deiodinase	Enzyme	P55073	Homo sapiens
MMDBp0196982	Sulfotransferase 6B1	Unknown	Q6IMI4

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001498	3,5-Diiodo-L-tyrosine	2-Aminoacrylic acid	Thyroid peroxidase	Iodide:Hydrogen-Peroxide Oxidoreductase 4	VMH	2997169 3153466 3475693
MMDBr0002252	Hydrogen carbonate	Hydrogen carbonate	Solute carrier organic anion transporter family, member 1a2	T4 Transport via Bicarbonate Antiport	VMH	12507753 9007731 9334206
MMDBr0002253	Thyroxine	Thyroxine	Solute carrier family 16, member 2 (thyroid hormone transporter)	T4 Transport via Facilitated Diffusion	VMH	12871948 7981683
MMDBr0003593	Glutathione	Glutathione	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076394 11076396 14579113
MMDBr0003604	1-(S-Glutathionyl)-2,4-Dinitrobenzene	1-(S-Glutathionyl)-2,4-Dinitrobenzene	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076396 14579113
MMDBr0003605	S-Glutathionyl-Ethacrynic-Acid	S-Glutathionyl-Ethacrynic-Acid	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076396 14579113
MMDBr0003910	Thyroxine	3,5,3,5-Tetraiodo-L-Thyronine-Beta-D-Glucuronoside	Udp glucuronosyltransferase 1 family, polypeptide a8	Glucuronosyltransferase	VMH	7263841 8405382
MMDBr0003911	Thyroxine	3,5,3,5-Tetraiodo-L-Thyronine-Beta-D-Glucuronoside	Udp glucuronosyltransferase 1 family, polypeptide a10	Glucuronosyltransferase	VMH	7263841 8405382
MMDBr0010436	Iodide	NADPH	Deiodinase, iodothyronine, type i	L-Thyroxine Iodohydrolase (Reducing)	VMH; KEGG	30371894
MMDBr0010437	Iodide	NADPH	Deiodinase, iodothyronine, type i	Thyroxine 5'-Deiodinase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Anorexia nervosa	Slight Decrease	Association	Human Blood	HMDB	10197568
Hypothyroidism		Association	Human Blood	HMDB	9849813
Proteinuria		Association	Human Urine	HMDB	18238748

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human stool; Human ; Human urine; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.0953				uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	7951484
Human Blood	Detected and Quantified	0.000011	0.0000016			uM	Adolescent (13-18 years old)	Female	Anorexia nervosa	HMDB	10197568
Human Blood	Detected and Quantified	0.0579				uM	Newborn (0-30 days old)	Male	Diabetes Mellitus, Congenital Insulin-dependent, With Fatal Secretory Diarrhea; Immunodeficiency, Polyendocrinopathy, and Enteropathy, X-linked, Formerly	HMDB	11295725
Human Blood	Detected and Quantified	0.0000185	0.0000052			uM	Adult (>18 years old)	Both	Hypothyroidism	HMDB	9849813
Human Blood	Detected and Quantified			0.0180	0.0206	uM	Children (1-13 years old)	Male	Hypothyroidism, congenital, nongoitrous, 2	HMDB	7234795
Human Blood	Detected and Quantified			23	55.2	uM	Children (1-13 years old)	Both	Hypothyroidism, congenital, nongoitrous, 2	HMDB	17468187
Human Blood	Detected and Quantified	0.0747				uM	Infant (0-1 year old)	Female	Leptin Deficiency or Dysfunction	HMDB	10486419
Human Blood	Detected and Quantified			0.0260	0.164	uM	Infant (0-1 year old)	Male	Pendred Syndrome	HMDB	1389454
Human Blood	Detected and Quantified			0.0540	0.112	uM	Newborn (0-30 days old)	Both	Pendred Syndrome	HMDB	1389454
Human Blood	Detected and Quantified	0.00000219				uM	Adult (>18 years old)	Male	Pituitary Hormone Deficiency, Combined, 1	HMDB	28356564
Human Blood	Detected and Quantified	0.00000557				uM	Children (1-13 years old)	Male	Pituitary Hormone Deficiency, Combined, 1	HMDB	28356564
Human Blood	Detected and Quantified	0.000009				uM	Children (1-13 years old)	Female	Pituitary Hormone Deficiency, Combined, 1	HMDB	25161449
Human Blood	Detected and Quantified	<0.0100				uM	Children (1-13 years old)	Male	Pituitary Hormone Deficiency, Combined, 1	HMDB	28356564
Human Blood	Detected and Quantified	0.000009				uM	Adult (>18 years old)	Female	Proprotein Convertase 1/3 Deficiency	HMDB	7477119
Human Urine	Detected and Quantified	0.0015	0.00154			umol/mmol creatinine	Adult (>18 years old)	Both	Proteinuria	HMDB	18238748
Human Saliva	Detected and Quantified			0.0	1.0	uM	Adult (>18 years old)	Both	Normal	HMDB	15179829
Human Blood	Detected and Quantified			0.000009	0.00002	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	7477119
Human Blood	Detected and Quantified			0.00001	0.000023	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	28356564
Human Blood	Detected and Quantified			0.000012	0.000025	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	28356564
Human Blood	Detected and Quantified	0.0000144	0.0000036			uM	Adolescent (13-18 years old)	Female	Normal	HMDB	10197568
Human Blood	Detected and Quantified	0.000016		0.0000064	0.000064	uM	Adult (>18 years old)	Both	Normal	HMDB	17936741
Human Urine	Detected and Quantified	0.00032	0.00015			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18238748
Human Blood	Detected and Quantified			0.0515	0.142	uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	10486419
Human Blood	Detected and Quantified			0.0579	0.148	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	7234795
Human Blood	Detected and Quantified			0.0600	0.150	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	28356564
Human Blood	Detected and Quantified			0.0700	0.175	uM	Infant (0-1 year old)	Both	Normal	HMDB	1389454
Human Blood	Detected and Quantified			0.105	0.215	uM	Newborn (0-30 days old)	Both	Normal	HMDB	1389454
Human Blood	Detected and Quantified	0.13	0.0061			uM	Children (1-13 years old)	Both	Normal	HMDB	10731506
Human Blood	Detected and Quantified			60	160	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	17468187
Human Blood	Detected and Quantified			0.000009	0.000023	uM		Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.00002		0.00001	0.00003	uM	Adult (>18 years old)	Both	Normal	HMDB	Wu AHB. Tietz clinical guide to laboratory tests. 4th ed. St. Louis: Saunders/Elsevier, 2006.
Human Blood	Detected and Quantified			0.000010	0.000023	uM	Adult (>18 years old)	Female	Normal	HMDB	K&S Clinical Diagnostics (http://www.ksdiagnostics.com)
Human Blood	Detected and Quantified			0.000010	0.000023	uM	Adult (>18 years old)	Male	Normal	HMDB	K&S Clinical Diagnostics (http://www.ksdiagnostics.com)
Human Blood	Detected and Quantified			0.000010	0.000023	uM	Adult (>18 years old)	Both	Normal	HMDB	K&S Clinical Diagnostics (http://www.ksdiagnostics.com)
Human Blood	Detected and Quantified			0.0399	0.162	uM	Adult (>18 years old)	Both	Normal	HMDB	K&S Clinical Diagnostics (http://www.ksdiagnostics.com)
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Ovary	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Thyroid gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000248

DrugBank ID

DB00451

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5614

KEGG Compound ID

C01829

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levothyroxine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18332

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Marks P, Anderson J, Vincent R: Aldosterone in myxoedema. Lancet. 1978 Dec 16;2(8103):1277-8. doi: 10.1016/s0140-6736(78)92040-8. [PubMed:82781 ]
Etling N, Gehin-Fouque F, Vielh JP, Gautray JP: The iodine content of amniotic fluid and placental transfer of iodinated drugs. Obstet Gynecol. 1979 Mar;53(3):376-80. [PubMed:424113 ]
Bode HH, Vanjonack WJ, Crawford JD: Mitigation of cretinism by breast-feeding. Pediatrics. 1978 Jul;62(1):13-6. [PubMed:683777 ]
Kurz W, Wittlinger G, Litmanovitch YI, Romanoff H, Pfeifer Y, Tal E, Sulman FG: Effect of manual lymph drainage massage on urinary excretion of neurohormones and minerals in chronic lymphedema. Angiology. 1978 Oct;29(10):764-72. doi: 10.1177/000331977802901007. [PubMed:717839 ]
Sutherland RL, Simpson-Morgan MW: The thyroxine-binding properties of serum proteins. A competitive binding technique employing sephadex G-25. J Endocrinol. 1975 Jun;65(3):319-32. doi: 10.1677/joe.0.0650319. [PubMed:807668 ]
Kahan IL, Varsanyi-Nagy M, Toth M, Nadrai A: The possible role of tear fluid thyroxine in keratoconus development. Exp Eye Res. 1990 Apr;50(4):339-43. doi: 10.1016/0014-4835(90)90134-g. [PubMed:2338121 ]
Randolph VS: Four clinical chemistry analyses for pediatric patients: glycosylated hemoglobin, free bilirubin, sweat electrolytes, neonatal thyroxine. Am J Med Technol. 1982 Jan;48(1):15-22. [PubMed:7041647 ]
Hays MT, McGuire RA, Hoogeveen JT, Diezeraad KN: Measurement method for radioactive thyroxine, triiodothyronine, iodide, and iodoprotein in samples with low activity. J Nucl Med. 1980 Mar;21(3):225-32. [PubMed:7365515 ]
Gil-Loyzaga P, Remezal M, Mollicone R, Ibanez A, Oriol R: H and B human blood-group antigen expression in cochlear hair cells is modulated by thyroxine. Cell Tissue Res. 1994 May;276(2):239-43. doi: 10.1007/BF00306109. [PubMed:8020061 ]
Braley-Mullen H, Sharp GC: A thyroxine-containing thyroglobulin peptide induces both lymphocytic and granulomatous forms of experimental autoimmune thyroiditis. J Autoimmun. 1997 Dec;10(6):531-40. doi: 10.1006/jaut.1997.0160. [PubMed:9451592 ]
Zenovko EI, Pavlov BA, Koreshkov GG, Gudukina GN, Sonkina EG: [Hypothalamo-pituitary-thyroid system in patients with rheumatoid arthritis]. Ter Arkh. 1998;70(1):49-52. [PubMed:9532653 ]
Jagannathan NR, Tandon N, Raghunathan P, Kochupillai N: Reversal of abnormalities of myelination by thyroxine therapy in congenital hypothyroidism: localized in vivo proton magnetic resonance spectroscopy (MRS) study. Brain Res Dev Brain Res. 1998 Aug 8;109(2):179-86. doi: 10.1016/s0165-3806(98)00081-9. [PubMed:9729372 ]
Raghu P, Reddy GB, Sivakumar B: Inhibition of transthyretin amyloid fibril formation by 2,4-dinitrophenol through tetramer stabilization. Arch Biochem Biophys. 2002 Apr 1;400(1):43-7. doi: 10.1006/abbi.2002.2779. [PubMed:11913969 ]
van Wassenaer AG, Stulp MR, Valianpour F, Tamminga P, Ris Stalpers C, de Randamie JS, van Beusekom C, de Vijlder JJ: The quantity of thyroid hormone in human milk is too low to influence plasma thyroid hormone levels in the very preterm infant. Clin Endocrinol (Oxf). 2002 May;56(5):621-7. doi: 10.1046/j.1365-2265.2002.01526.x. [PubMed:12030913 ]
Benvenga S, Alesci S, Trimarchi F: High-density lipoprotein-facilitated entry of thyroid hormones into cells: a mechanism different from the low-density lipoprotein-facilitated entry. Thyroid. 2002 Jul;12(7):547-56. doi: 10.1089/105072502320288384. [PubMed:12193297 ]
Gil'miiarova FN, Pervova IuV, Radomskaia VM, Gergel' NI, Tarasova SV: [Levels of unified metabolites and thyroid hormones in blood and oral fluid of children with minimal brain dysfunction]. Biomed Khim. 2004 Mar-Apr;50(2):204-10. [PubMed:15179829 ]
Escobar-Morreale HF, Botella-Carretero JI, Gomez-Bueno M, Galan JM, Barrios V, Sancho J: Thyroid hormone replacement therapy in primary hypothyroidism: a randomized trial comparing L-thyroxine plus liothyronine with L-thyroxine alone. Ann Intern Med. 2005 Mar 15;142(6):412-24. doi: 10.7326/0003-4819-142-6-200503150-00007. [PubMed:15767619 ]
Hausman GJ, Wright JT, Latimer A, Watson R, Martin RJ: The influence of human growth hormone (GH) and thyroxine (T4) on the differentiation of adipose tissue in the fetus. Obes Res. 1993 Sep;1(5):345-56. doi: 10.1002/j.1550-8528.1993.tb00012.x. [PubMed:16350585 ]
Hekimsoy Z, Oktem IK: Serum creatine kinase levels in overt and subclinical hypothyroidism. Endocr Res. 2005;31(3):171-5. doi: 10.1080/07435800500371706. [PubMed:16392619 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

Showing metabocard for Thyroxine (MMDBc0000337)

MOL for #<Metabolite:0x0000564af1d614a0>

3D MOL for #<Metabolite:0x0000564af1d614a0>

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3D PDB for #<Metabolite:0x0000564af1d614a0>

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Structure for #<Metabolite:0x0000564af1d614a0>

3D Structure for #<Metabolite:0x0000564af1d614a0>