NP-MRD: Showing NP-Card for Thyroxine (NP0000418)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-07-01 14:27:35 UTC

NP-MRD ID

NP0000418

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thyroxine

Description

Thyroxine (3,5,3′,5′-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′-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>
NP0000418

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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

Chemical Formula

C₁₅H₁₁I₄NO₄

Average Mass

776.8700 Da

Monoisotopic Mass

776.68668 Da

IUPAC Name

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

Traditional Name

levothyroxine

CAS Registry Number

51-48-9

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Homo sapiens	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	235.5 °C	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	0.009 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

External Links

HMDB ID

HMDB0000248

DrugBank ID

DB00451

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB112159

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

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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. [PubMed:2338121 ]
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. [PubMed:9729372 ]
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. [PubMed:717839 ]
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 ]
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. [PubMed:12030913 ]
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 ]
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 ]
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 ]
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. [PubMed:12193297 ]
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. [PubMed:16350585 ]
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. [PubMed:8020061 ]
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. [PubMed:15767619 ]
Bode HH, Vanjonack WJ, Crawford JD: Mitigation of cretinism by breast-feeding. Pediatrics. 1978 Jul;62(1):13-6. [PubMed:683777 ]
Marks P, Anderson J, Vincent R: Aldosterone in myxoedema. Lancet. 1978 Dec 16;2(8103):1277-8. [PubMed:82781 ]
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. [PubMed:807668 ]
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. [PubMed:9451592 ]
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. [PubMed:11913969 ]
Hekimsoy Z, Oktem IK: Serum creatine kinase levels in overt and subclinical hypothyroidism. Endocr Res. 2005;31(3):171-5. [PubMed:16392619 ]

Showing NP-Card for Thyroxine (NP0000418)

MOL for NP0000418 (Thyroxine)

3D MOL for NP0000418 (Thyroxine)

3D SDF for NP0000418 (Thyroxine)

3D-SDF for NP0000418 (Thyroxine)

PDB for NP0000418 (Thyroxine)

3D PDB for NP0000418 (Thyroxine)

SMILES for NP0000418 (Thyroxine)

INCHI for NP0000418 (Thyroxine)

Structure for NP0000418 (Thyroxine)

3D Structure for NP0000418 (Thyroxine)