NP-MRD: Showing NP-Card for L-Thyronine (NP0000208)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:13:41 UTC

NP-MRD ID

NP0000208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Thyronine

Description

Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles. (If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in goitre.) Via a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues in the thyroglobulin molecules, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one particle of MIT and one particle of DIT produces triiodothyronine. The thyronamines function via some unknown mechanism to inhibit neuronal activity; this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature. Both T3 and T4 are used to treat thyroid hormone deficiency (hypothyroidism). They are both absorbed well by the gut, so can be given orally. Levothyroxine, the most commonly used synthetic thyroxine form, is a stereoisomer of physiological thyroxine, which is metabolised more slowly and hence usually only needs once-daily administration. Natural desiccated thyroid hormones, which are derived from pig thyroid glands, are a "natural" hypothyroid treatment containing 20% T3 and traces of T2, T1 and calcitonin. A group of metabolites derived from thyroxine and triiodothyronine via the peripheral enzymatic removal of iodines from the thyroxine nucleus. Thyronine is the thyroxine nucleus devoid of its four iodine atoms.

Structure

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

HMDB0000667
     RDKit          3D
L-Thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.1977    2.1484    0.1746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081    0.9583    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3407   -0.0263   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095   -0.4557   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435   -1.5567    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.9379    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310   -1.2210    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8051   -1.6073    0.9778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.8804    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862    0.2015    1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943    0.9142    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    0.5780   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2914    1.2954   -0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060   -0.5022   -0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992   -1.2181   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -0.1247   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.2205   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    0.3450    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.8378    2.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -0.8098    1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789    2.5384   -0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    2.8004    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9507    1.2755   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2728    0.4358   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.9171   -0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -2.1351    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -2.8044    1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    0.5154    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568    1.7598    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    2.0894   -1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -0.7569   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601   -2.0640   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    0.4323   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464    1.0797   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -1.4082    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 17  4  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
M  END

L-Thyronine.mol
  Mrv1652305271900192D          

 20 21  0  0  0  0            999 V2000
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
  5 18  1  0  0  0  0
  1 19  2  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000208

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
KKCIOUWDFWQUBT-AWEZNQCLSA-N

> <FORMULA>
C15H15NO4

> <MOLECULAR_WEIGHT>
273.2839

> <EXACT_MASS>
273.100107973

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.720858323594932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
0.011688075180960931

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.895019385843883

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6067971044923706

> <JCHEM_PKA_STRONGEST_BASIC>
9.261323301384072

> <JCHEM_POLAR_SURFACE_AREA>
92.78000000000002

> <JCHEM_REFRACTIVITY>
73.33800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thyronine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000667
     RDKit          3D
L-Thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.1977    2.1484    0.1746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081    0.9583    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3407   -0.0263   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095   -0.4557   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435   -1.5567    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.9379    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310   -1.2210    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8051   -1.6073    0.9778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.8804    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862    0.2015    1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943    0.9142    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    0.5780   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2914    1.2954   -0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060   -0.5022   -0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992   -1.2181   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -0.1247   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.2205   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    0.3450    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.8378    2.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -0.8098    1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789    2.5384   -0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    2.8004    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9507    1.2755   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2728    0.4358   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.9171   -0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -2.1351    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -2.8044    1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    0.5154    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568    1.7598    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    2.0894   -1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -0.7569   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601   -2.0640   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    0.4323   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464    1.0797   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -1.4082    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 17  4  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
M  END

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

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

HMDB0000667
     RDKit          3D
L-Thyronine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.1977    2.1484    0.1746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081    0.9583    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3407   -0.0263   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095   -0.4557   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435   -1.5567    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.9379    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310   -1.2210    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8051   -1.6073    0.9778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -0.8804    0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862    0.2015    1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943    0.9142    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    0.5780   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2914    1.2954   -0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060   -0.5022   -0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992   -1.2181   -0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950   -0.1247   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.2205   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    0.3450    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.8378    2.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -0.8098    1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789    2.5384   -0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    2.8004    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9507    1.2755   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2728    0.4358   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.9171   -0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -2.1351    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714   -2.8044    1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    0.5154    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568    1.7598    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    2.0894   -1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -0.7569   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601   -2.0640   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    0.4323   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464    1.0797   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -1.4082    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
 17  4  1  0
 15  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
M  END

View in JSmol

Synonyms

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

Chemical Formula

C₁₅H₁₅NO₄

Average Mass

273.2839 Da

Monoisotopic Mass

273.10011 Da

IUPAC Name

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

Traditional Name

thyronine

CAS Registry Number

1596-67-4

SMILES

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

InChI Identifier

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

InChI Key

KKCIOUWDFWQUBT-AWEZNQCLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, simulated)	V.dorna83			2021-08-23	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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-08-01	View Spectrum

Species

Species of Origin

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

thyronine (CHEBI:30662 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	255 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	0.012	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	1.61	ChemAxon
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.34 m³·mol⁻¹	ChemAxon
Polarizability	27.72 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000667

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022172

KNApSAcK ID

Not Available

Chemspider ID

4574450

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thyronine

METLIN ID

5637

PubChem Compound

5461103

PDB ID

Not Available

ChEBI ID

30662

Good Scents ID

Not Available

References

General References

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

Showing NP-Card for L-Thyronine (NP0000208)

MOL for NP0000208 (L-Thyronine)

3D MOL for NP0000208 (L-Thyronine)

3D SDF for NP0000208 (L-Thyronine)

3D-SDF for NP0000208 (L-Thyronine)

PDB for NP0000208 (L-Thyronine)

3D PDB for NP0000208 (L-Thyronine)

SMILES for NP0000208 (L-Thyronine)

INCHI for NP0000208 (L-Thyronine)

Structure for NP0000208 (L-Thyronine)

3D Structure for NP0000208 (L-Thyronine)