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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014651

Secondary Accession Numbers

HMDB14651

Metabolite Identification

Common Name

Dextrothyroxine

Description

The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism. [PubChem]

Structure

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

HMDB0014651
     RDKit          3D
Dextrothyroxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.5360   -1.0756    0.6331 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4435   -0.1325   -0.4513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2320   -0.3364   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577   -0.2144   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -1.2890    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -1.1617    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8071   -2.8189    1.5996 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005    0.0662    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    0.2363    1.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229    0.1149    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824    0.2978    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3289    0.1756    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0953    0.4644    2.0913 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.3817   -0.1348   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -0.2614   -0.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2523   -0.3267   -1.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370   -0.8037   -3.1690 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.0241   -0.1962   -0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    1.1438    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    3.0240    0.2984 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    1.0112   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    1.2696   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5062    2.1476   -0.9270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7471    1.7037    1.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9994   -0.6886    1.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578   -2.0063    0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3335   -0.3399   -1.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2736   -1.3486   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511    0.4539   -2.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8226   -2.2424   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415    0.5416    2.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4734   -0.1322   -0.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1227   -0.3407   -1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720    1.8975   -0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3369    1.3019    2.0834 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  6
  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


  Mrv0541 04191212132D          

 24 25  0  0  1  0            999 V2000
    1.3047    0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -0.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5902   -0.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243   -0.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243    0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5902    0.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4481    0.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4481    1.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336    0.3228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0192    0.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336   -0.5022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.3228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5902   -1.7397    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387   -0.9147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6966    0.7353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6966   -0.9147    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -0.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -0.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2677   -0.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532    0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821    0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387    0.7353    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2677    0.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2677    1.5603    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
  8  7  2  0  0  0  0
 12  7  1  0  0  0  0
 10  9  1  0  0  0  0
  9 11  1  6  0  0  0
  1 10  1  0  0  0  0
  4 14  1  0  0  0  0
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  5  4  2  0  0  0  0
  3  4  1  0  0  0  0
  3  2  2  0  0  0  0
  5  6  1  0  0  0  0
 13  3  1  0  0  0  0
 14 17  1  0  0  0  0
 21 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 23  2  0  0  0  0
 23 21  1  0  0  0  0
 18 21  2  0  0  0  0
  5 22  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014651

> <DATABASE_NAME>
hmdb

> <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-/m1/s1

> <INCHI_KEY>
XUIIKFGFIJCVMT-GFCCVEGCSA-N

> <FORMULA>
C15H11I4NO4

> <MOLECULAR_WEIGHT>
776.87

> <EXACT_MASS>
776.686681525

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
49.311808389762874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
3.727307065150786

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.426761076903324

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.2733674568179616

> <JCHEM_PKA_STRONGEST_BASIC>
9.433364269994815

> <JCHEM_POLAR_SURFACE_AREA>
92.78000000000002

> <JCHEM_REFRACTIVITY>
126.788

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dextrothyroxine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014651
     RDKit          3D
Dextrothyroxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.5360   -1.0756    0.6331 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4435   -0.1325   -0.4513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2320   -0.3364   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577   -0.2144   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -1.2890    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -1.1617    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8071   -2.8189    1.5996 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005    0.0662    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    0.2363    1.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229    0.1149    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824    0.2978    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3289    0.1756    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0953    0.4644    2.0913 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.3817   -0.1348   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -0.2614   -0.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2523   -0.3267   -1.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370   -0.8037   -3.1690 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.0241   -0.1962   -0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    1.1438    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    3.0240    0.2984 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    1.0112   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    1.2696   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5062    2.1476   -0.9270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7471    1.7037    1.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9994   -0.6886    1.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578   -2.0063    0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3335   -0.3399   -1.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2736   -1.3486   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511    0.4539   -2.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8226   -2.2424   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415    0.5416    2.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4734   -0.1322   -0.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1227   -0.3407   -1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720    1.8975   -0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3369    1.3019    2.0834 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  6
  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                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       2.435   0.603   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.435  -0.937   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.102  -1.707   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.232  -0.937   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.232   0.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.102   1.373   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.436   1.373   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.436   2.913   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.103   0.603   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.769   1.373   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.103  -0.937   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       7.770   0.603   0.000  0.00  0.00           O+0
HETATM   13  I   UNK     0       1.102  -3.247   0.000  0.00  0.00           I+0
HETATM   14  O   UNK     0      -1.566  -1.707   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -6.900   1.373   0.000  0.00  0.00           O+0
HETATM   16  I   UNK     0      -6.900  -1.707   0.000  0.00  0.00           I+0
HETATM   17  C   UNK     0      -2.899  -0.937   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.567  -0.937   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.233  -1.707   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.899   0.603   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.567   0.603   0.000  0.00  0.00           C+0
HETATM   22  I   UNK     0      -1.566   1.373   0.000  0.00  0.00           I+0
HETATM   23  C   UNK     0      -4.233   1.373   0.000  0.00  0.00           C+0
HETATM   24  I   UNK     0      -4.233   2.913   0.000  0.00  0.00           I+0
CONECT    1   10    2    6                                                  
CONECT    2    1    3                                                       
CONECT    3    4    2   13                                                  
CONECT    4   14    5    3                                                  
CONECT    5    4    6   22                                                  
CONECT    6    1    5                                                       
CONECT    7    9    8   12                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    7                                                            
CONECT   13    3                                                            
CONECT   14    4   17                                                       
CONECT   15   21                                                            
CONECT   16   18                                                            
CONECT   17   14   19   20                                                  
CONECT   18   16   19   21                                                  
CONECT   19   17   18                                                       
CONECT   20   17   23                                                       
CONECT   21   15   23   18                                                  
CONECT   22    5                                                            
CONECT   23   20   21   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0014651
HETATM    1  N1  UNL     1      -4.536  -1.076   0.633  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.443  -0.133  -0.451  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.232  -0.336  -1.301  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.958  -0.214  -0.590  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.326  -1.289   0.019  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.125  -1.162   0.686  1.00  0.00           C  
HETATM    7  I1  UNL     1       0.807  -2.819   1.600  1.00  0.00           I  
HETATM    8  C6  UNL     1       0.500   0.066   0.770  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.703   0.236   1.428  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.923   0.115   0.838  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.082   0.298   1.553  1.00  0.00           C  
HETATM   12  C9  UNL     1       5.329   0.176   0.959  1.00  0.00           C  
HETATM   13  I2  UNL     1       7.095   0.464   2.091  1.00  0.00           I  
HETATM   14  C10 UNL     1       5.382  -0.135  -0.371  1.00  0.00           C  
HETATM   15  O2  UNL     1       6.622  -0.261  -0.983  1.00  0.00           O  
HETATM   16  C11 UNL     1       4.252  -0.327  -1.126  1.00  0.00           C  
HETATM   17  I3  UNL     1       4.337  -0.804  -3.169  1.00  0.00           I  
HETATM   18  C12 UNL     1       3.024  -0.196  -0.497  1.00  0.00           C  
HETATM   19  C13 UNL     1      -0.114   1.144   0.171  1.00  0.00           C  
HETATM   20  I4  UNL     1       0.840   3.024   0.298  1.00  0.00           I  
HETATM   21  C14 UNL     1      -1.333   1.011  -0.505  1.00  0.00           C  
HETATM   22  C15 UNL     1      -4.569   1.270  -0.025  1.00  0.00           C  
HETATM   23  O3  UNL     1      -4.506   2.148  -0.927  1.00  0.00           O  
HETATM   24  O4  UNL     1      -4.747   1.704   1.261  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.999  -0.689   1.479  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.858  -2.006   0.356  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.334  -0.340  -1.116  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.274  -1.349  -1.759  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.251   0.454  -2.096  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.823  -2.242  -0.054  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.042   0.542   2.598  1.00  0.00           H  
HETATM   32  H8  UNL     1       7.473  -0.132  -0.480  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.123  -0.341  -1.062  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.772   1.897  -0.960  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.337   1.302   2.083  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

HMDB0014651
     RDKit          3D
Dextrothyroxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.5360   -1.0756    0.6331 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4435   -0.1325   -0.4513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2320   -0.3364   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577   -0.2144   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -1.2890    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -1.1617    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8071   -2.8189    1.5996 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005    0.0662    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    0.2363    1.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229    0.1149    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824    0.2978    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3289    0.1756    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0953    0.4644    2.0913 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.3817   -0.1348   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -0.2614   -0.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2523   -0.3267   -1.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370   -0.8037   -3.1690 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.0241   -0.1962   -0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    1.1438    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    3.0240    0.2984 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    1.0112   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    1.2696   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5062    2.1476   -0.9270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7471    1.7037    1.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9994   -0.6886    1.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578   -2.0063    0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3335   -0.3399   -1.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2736   -1.3486   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511    0.4539   -2.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8226   -2.2424   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415    0.5416    2.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4734   -0.1322   -0.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1227   -0.3407   -1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720    1.8975   -0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3369    1.3019    2.0834 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  6
  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 View Stereo Labels

Synonyms

Value	Source
D-T4	ChEBI
DT4	ChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-D-tyrosine	ChEBI
D-Thyroxine	HMDB
Choloxin	HMDB
Sodium dextrothyroxine	HMDB
D Thyroxine	HMDB
D-T4 Thyroid hormone	HMDB
Dextrothyroxine sodium	HMDB
Dextrothyroxine	ChEBI

Chemical Formula

C₁₅H₁₁I₄NO₄

Average Molecular Weight

776.87

Monoisotopic Molecular Weight

776.686681525

IUPAC Name

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

Traditional Name

dextrothyroxine

CAS Registry Number

51-49-0

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-/m1/s1

InChI Key

XUIIKFGFIJCVMT-GFCCVEGCSA-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
D-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

thyroxine (CHEBI:30659 )
D-tyrosine derivative (CHEBI:30659 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014651)
Membrane (HMDB: HMDB0014651)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235 - 236 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.009 g/L	Not Available
LogP	4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	49.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	217.542	30932474
DeepCCS	[M-H]-	214.992	30932474
DeepCCS	[M-2H]-	249.21	30932474
DeepCCS	[M+Na]+	224.563	30932474
AllCCS	[M+H]+	207.3	32859911
AllCCS	[M+H-H2O]+	206.5	32859911
AllCCS	[M+NH4]+	207.9	32859911
AllCCS	[M+Na]+	208.1	32859911
AllCCS	[M-H]-	203.6	32859911
AllCCS	[M+Na-2H]-	205.7	32859911
AllCCS	[M+HCOO]-	208.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dextrothyroxine	N[C@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O	4887.2	Standard polar	33892256
Dextrothyroxine	N[C@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O	3942.7	Standard non polar	33892256
Dextrothyroxine	N[C@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O	4159.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrothyroxine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-4002002900-0d489fed1cb888a2d9d0	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrothyroxine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrothyroxine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrothyroxine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrothyroxine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrothyroxine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrothyroxine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 10V, Positive-QTOF	splash10-01si-0000000900-524d052a32c1fe4b904d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 20V, Positive-QTOF	splash10-001i-0000001900-553f6a4045ef2241fd85	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 40V, Positive-QTOF	splash10-014i-0009000000-d2431d885a79bb80b7a5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 10V, Negative-QTOF	splash10-004i-0000000900-137b5f8f48031bc9aa4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 20V, Negative-QTOF	splash10-03fr-0004001900-db1d8cdb93785d786382	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 40V, Negative-QTOF	splash10-0h9u-7029014300-3bd9620b0c6a8dd20c93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 10V, Positive-QTOF	splash10-004i-0000000900-d76aec17d3d890cb64c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 20V, Positive-QTOF	splash10-001i-0000001900-daf0bb8e065f55b0cda3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 40V, Positive-QTOF	splash10-001i-0001013900-6d1177cb9a243bb761eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 10V, Negative-QTOF	splash10-004i-0000000900-95266ab7e52b7d3cb322	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 20V, Negative-QTOF	splash10-004i-1700000900-195c16ab7434b857e712	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrothyroxine 40V, Negative-QTOF	splash10-004i-0900000000-0dba40d354fa6a5575e0	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00509	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00509	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00509

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dextrothyroxine

METLIN ID

Not Available

PubChem Compound

8730

PDB ID

Not Available

ChEBI ID

30659

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Uchino H, Kanai Y, Kim DK, Wempe MF, Chairoungdua A, Morimoto E, Anders MW, Endou H: Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition. Mol Pharmacol. 2002 Apr;61(4):729-37. [PubMed:11901210 ]

Enzymes

Enzyme Details

1. Thyroid peroxidase

General function:: Involved in calcium ion binding
Specific function:: Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:: TPO
Uniprot ID:: P07202
Molecular weight:: 102961.63

References

Visser TJ: The elemental importance of sufficient iodine intake: a trace is not enough. Endocrinology. 2006 May;147(5):2095-7. [PubMed:16617153 ]

Enzyme Details

2. Thyroid hormone receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: High affinity receptor for triiodothyronine
Gene Name:: THRB
Uniprot ID:: P10828
Molecular weight:: 52787.2

References

Bernal J: Thyroid hormone receptors in brain development and function. Nat Clin Pract Endocrinol Metab. 2007 Mar;3(3):249-59. [PubMed:17315033 ]
Gonzalez-Sancho JM, Garcia V, Bonilla F, Munoz A: Thyroid hormone receptors/THR genes in human cancer. Cancer Lett. 2003 Mar 31;192(2):121-32. [PubMed:12668276 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Yen PM, Feng X, Flamant F, Chen Y, Walker RL, Weiss RE, Chassande O, Samarut J, Refetoff S, Meltzer PS: Effects of ligand and thyroid hormone receptor isoforms on hepatic gene expression profiles of thyroid hormone receptor knockout mice. EMBO Rep. 2003 Jun;4(6):581-7. [PubMed:12776178 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Wu SY, Sadow PM, Refetoff S, Weiss RE: Tissue responses to thyroid hormone in a kindred with resistance to thyroid hormone harboring a commonly occurring mutation in the thyroid hormone receptor beta gene (P453T). J Lab Clin Med. 2005 Aug;146(2):85-94. [PubMed:16099238 ]

Enzyme Details

3. Thyroid hormone receptor alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. High affinity receptor for triiodothyronine
Gene Name:: THRA
Uniprot ID:: P10827
Molecular weight:: 54815.1

References

Jiang W, Miyamoto T, Kakizawa T, Sakuma T, Nishio S, Takeda T, Suzuki S, Hashizume K: Expression of thyroid hormone receptor alpha in 3T3-L1 adipocytes; triiodothyronine increases the expression of lipogenic enzyme and triglyceride accumulation. J Endocrinol. 2004 Aug;182(2):295-302. [PubMed:15283690 ]
Kariv R, Enden A, Zvibel I, Rosner G, Brill S, Shafritz DA, Halpern Z, Oren R: Triiodothyronine and interleukin-6 (IL-6) induce expression of HGF in an immortalized rat hepatic stellate cell line. Liver Int. 2003 Jun;23(3):187-93. [PubMed:12955882 ]
Mai W, Janier MF, Allioli N, Quignodon L, Chuzel T, Flamant F, Samarut J: Thyroid hormone receptor alpha is a molecular switch of cardiac function between fetal and postnatal life. Proc Natl Acad Sci U S A. 2004 Jul 13;101(28):10332-7. Epub 2004 Jul 6. [PubMed:15240882 ]
Sciaudone MP, Yao L, Schaller M, Zinn SA, Freake HC: Diethylenetriaminepentaacetic acid enhances thyroid hormone action by a transcriptional mechanism. Biol Trace Elem Res. 2004 Summer;99(1-3):219-31. [PubMed:15235154 ]
Timmer DC, Bakker O, Wiersinga WM: Triiodothyronine affects the alternative splicing of thyroid hormone receptor alpha mRNA. J Endocrinol. 2003 Nov;179(2):217-25. [PubMed:14596673 ]
Bernal J: Thyroid hormone receptors in brain development and function. Nat Clin Pract Endocrinol Metab. 2007 Mar;3(3):249-59. [PubMed:17315033 ]

Showing metabocard for Dextrothyroxine (HMDB0014651)

MOL for HMDB0014651 (Dextrothyroxine)

3D MOL for HMDB0014651 (Dextrothyroxine)

3D SDF for HMDB0014651 (Dextrothyroxine)

3D-SDF for HMDB0014651 (Dextrothyroxine)

PDB for HMDB0014651 (Dextrothyroxine)

3D PDB for HMDB0014651 (Dextrothyroxine)

SMILES for HMDB0014651 (Dextrothyroxine)

INCHI for HMDB0014651 (Dextrothyroxine)

Structure for HMDB0014651 (Dextrothyroxine)

3D Structure for HMDB0014651 (Dextrothyroxine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References