NP-MRD: Showing NP-Card for Levothyroxine (NP0338705)

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Record Information

Version

2.0

Created at

2024-09-11 17:09:42 UTC

Updated at

2024-09-11 17:09:42 UTC

NP-MRD ID

NP0338705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Levothyroxine

Description

Levothyroxine was first documented in 2024 (PMID: 39307136). Based on a literature review a small amount of articles have been published on Levothyroxine (PMID: 39295705) (PMID: 39290156) (PMID: 39287310) (PMID: 39286238).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262319412D          

 24 25  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  6  1  0  0  0  0
  2 11  2  0  0  0  0
  3  6  1  0  0  0  0
  3 12  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  7 24  1  0  0  0  0
  8 13  2  0  0  0  0
  8 16  1  0  0  0  0
  9 13  1  0  0  0  0
  9 17  1  0  0  0  0
 10 14  2  0  0  0  0
 10 18  1  0  0  0  0
 11 14  1  0  0  0  0
 11 19  1  0  0  0  0
 12 15  1  0  0  0  0
 12 20  1  0  0  0  0
 13 21  1  0  0  0  0
 14 24  1  0  0  0  0
 15 22  2  0  0  0  0
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/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)

> <INCHI_KEY>
XUIIKFGFIJCVMT-UHFFFAOYNA-N

> <FORMULA>
C15H11I4NO4

> <MOLECULAR_WEIGHT>
776.874

> <EXACT_MASS>
776.68669

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
49.37803814427795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
3.72730704982258

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.426761076989792

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.27345586539235944

> <JCHEM_PKA_STRONGEST_BASIC>
9.433364269995794

> <JCHEM_POLAR_SURFACE_AREA>
92.78000000000002

> <JCHEM_REFRACTIVITY>
126.788

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
thyroxine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  I   UNK     0     -12.003   2.310   0.000  0.00  0.00           I+0
HETATM   17  I   UNK     0      -9.336  -2.310   0.000  0.00  0.00           I+0
HETATM   18  I   UNK     0      -4.001   3.850   0.000  0.00  0.00           I+0
HETATM   19  I   UNK     0      -6.668  -0.770   0.000  0.00  0.00           I+0
HETATM   20  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1    6   10                                                       
CONECT    2    6   11                                                       
CONECT    3    6   12                                                       
CONECT    4    7    8                                                       
CONECT    5    7    9                                                       
CONECT    6    1    2    3                                                  
CONECT    7    4    5   24                                                  
CONECT    8    4   13   16                                                  
CONECT    9    5   13   17                                                  
CONECT   10    1   14   18                                                  
CONECT   11    2   14   19                                                  
CONECT   12    3   15   20                                                  
CONECT   13    8    9   21                                                  
CONECT   14   10   11   24                                                  
CONECT   15   12   22   23                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   15                                                            
CONECT   23   15                                                            
CONECT   24    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₁I₄NO₄

Average Mass

776.8740 Da

Monoisotopic Mass

776.68669 Da

IUPAC Name

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

Traditional Name

thyroxine

CAS Registry Number

Not Available

SMILES

NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O

InChI Identifier

InChI=1/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)

InChI Key

XUIIKFGFIJCVMT-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These 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
Phenoxy compound
2-iodophenol
2-halophenol
Phenol ether
Iodobenzene
Halobenzene
Aralkylamine
Phenol
Aryl halide
Aryl iodide
Monocyclic benzene moiety
Benzenoid
Amino acid
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organohalogen compound
Organoiodide
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:30660 )
tyrosine derivative (CHEBI:30660 )
iodothyronine (CHEBI:30660 )
iodophenol (CHEBI:30660 )
2-halophenol (CHEBI:30660 )
an iodoaromatic compound (THRYROXINE )
a hormone (THRYROXINE )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.73	ChemAxon
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	49.38 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

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

Not Available

Good Scents ID

Not Available

References

General References

Wang J, Hao J, Gao Y, Wang S, Wang D, Tao W, Duan R, Zhang Z, Gao M: Application value of iodine-131 combined with levothyroxine sodium in patients with differentiated thyroid cancer after surgery. Oncology. 2024 Sep 20:1-15. doi: 10.1159/000541546. [PubMed:39307136 ]
Alshaakh Mohd Mari A, Titus J, Zayat V, Kinaan M: A Malignant Duo: Mixed Medullary and Follicular Variant Papillary Thyroid Cancer. Cureus. 2024 Aug 19;16(8):e67231. doi: 10.7759/cureus.67231. eCollection 2024 Aug. [PubMed:39295705 ]
de Lima Beltrao FE, Carvalhal G, de Almeida Beltrao DC, de Lima Beltrao FE, Ribeiro MO, Ettleson MD, Ramos HE, Bianco AC: Treatment Preferences in Patients with Hypothyroidism: an Analysis of Eleven Randomized Controlled Trials. J Clin Endocrinol Metab. 2024 Sep 18:dgae651. doi: 10.1210/clinem/dgae651. [PubMed:39290156 ]
Lin H, Zhang X, Zheng Y, Tang C, Wang J: Research on the soothing Liver - Qi stagnation method in the treatment of postoperative papillary thyroid carcinoma patients' concomitant depression: A randomized controlled clinical trial. Medicine (Baltimore). 2024 Sep 13;103(37):e39325. doi: 10.1097/MD.0000000000039325. [PubMed:39287310 ]
Fortunati F, Froidure A, Baldin P, Horsmans Y, Lanthier N, Dahlqvist G, Delire B: Pirfenidone-induced liver injury, a case report of a rare idiosyncratic reaction. Ther Adv Drug Saf. 2024 Sep 14;15:20420986241270866. doi: 10.1177/20420986241270866. eCollection 2024. [PubMed:39286238 ]

Showing NP-Card for Levothyroxine (NP0338705)

MOL for NP0338705 (Levothyroxine)

3D MOL for NP0338705 (Levothyroxine)

3D SDF for NP0338705 (Levothyroxine)

3D-SDF for NP0338705 (Levothyroxine)

PDB for NP0338705 (Levothyroxine)

3D PDB for NP0338705 (Levothyroxine)

SMILES for NP0338705 (Levothyroxine)

INCHI for NP0338705 (Levothyroxine)

Structure for NP0338705 (Levothyroxine)

3D Structure for NP0338705 (Levothyroxine)