NP-MRD: Showing NP-Card for 3,3'-diiodo-l-thyronine (NP0299675)

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Record Information

Version

2.0

Created at

2022-09-10 11:38:12 UTC

Updated at

2022-09-10 11:38:12 UTC

NP-MRD ID

NP0299675

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,3'-diiodo-l-thyronine

Description

3,3'-Diiodo-L-thyronine, also known as 3,3'-T2, 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. 3,3'-diiodo-l-thyronine is found in Homo sapiens. 3,3'-Diiodo-L-thyronine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.5804   -1.0936    0.1870 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089   -0.4242    0.4476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1998   -1.0469   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -0.4405   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    0.5894   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315    1.1803   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6261    0.7358    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8519    1.3100    0.3173 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841    0.7291    0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677   -0.5589   -0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360   -1.1200   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6283   -0.3650   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9075   -0.9006   -0.1081 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868    0.9258    0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1898    2.0494    0.9650 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.2110    1.4482    0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853   -0.2897    0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -1.0223    2.5515 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -0.8890    0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4533    1.0236    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5107    1.8317    0.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6390    1.5848   -0.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5128   -2.1012    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8926   -0.9575   -0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -0.5331    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4865   -0.8939   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1719   -2.1441   -0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    0.9671   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200    1.9820   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -1.1592   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6965   -2.1299   -0.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7259   -0.3822    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1289    2.4640    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3627   -1.7039    1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5158    1.3346    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4 19  2  0
 19 17  1  0
 17 18  1  0
 17  7  2  0
  7  8  1  0
  8  9  1  0
  9 16  2  0
 16 14  1  0
 14 15  1  0
 14 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
  7  6  1  0
  6  5  2  0
  2 20  1  0
 20 22  1  0
 20 21  2  0
  5  4  1  0
 10  9  1  0
  2 25  1  1
  1 23  1  0
  1 24  1  0
  3 26  1  0
  3 27  1  0
 19 34  1  0
 16 33  1  0
 13 32  1  0
 11 31  1  0
 10 30  1  0
  6 29  1  0
  5 28  1  0
 22 35  1  0
M  END


  Mrv0541 05041411402D          

 23 24  0  0  1  0            999 V2000
   -0.7145   -2.8875    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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
   -1.4289   -2.4750    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    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
   -2.8579   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  2  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  3  1  0  0  0  0
 13 10  2  0  0  0  0
 14  4  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 12 18  1  1  0  0  0
 19 13  1  0  0  0  0
 20 15  2  0  0  0  0
 21 15  1  0  0  0  0
 22  9  1  0  0  0  0
 22 14  1  0  0  0  0
 12 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0299675

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H13I2NO4/c16-10-7-9(2-3-13(10)19)22-14-4-1-8(5-11(14)17)6-12(18)15(20)21/h1-5,7,12,19H,6,18H2,(H,20,21)/t12-/m0/s1

> <INCHI_KEY>
CPCJBZABTUOGNM-LBPRGKRZSA-N

> <FORMULA>
C15H13I2NO4

> <MOLECULAR_WEIGHT>
525.077

> <EXACT_MASS>
524.893394749

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.51040783368235

> <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-iodophenoxy)-3-iodophenyl]propanoic acid

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
1.8695015556014722

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.504080013009542

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.7536693906174272

> <JCHEM_PKA_STRONGEST_BASIC>
9.497536714228461

> <JCHEM_POLAR_SURFACE_AREA>
92.78

> <JCHEM_REFRACTIVITY>
100.06300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3'-diiodo-L-thyronine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  I   UNK     0       0.000   0.000   0.000  0.00  0.00           I+0
HETATM   17  I   UNK     0       0.000   0.000   0.000  0.00  0.00           I+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4    8                                                       
CONECT    2    3    9                                                       
CONECT    3    2   13                                                       
CONECT    4    1   14                                                       
CONECT    5    8   11                                                       
CONECT    6    8   12                                                       
CONECT    7    9   10                                                       
CONECT    8    1    5    6                                                  
CONECT    9    2    7   22                                                  
CONECT   10    7   13   16                                                  
CONECT   11    5   14   17                                                  
CONECT   12    6   15   18   23                                             
CONECT   13    3   10   19                                                  
CONECT   14    4   11   22                                                  
CONECT   15   12   20   21                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   15                                                            
CONECT   21   15                                                            
CONECT   22    9   14                                                       
CONECT   23   12                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-Amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoic acid	ChEBI
3,3'-DEIODO-thyroxine	ChEBI
O-(4-Hydroxy-3-iodophenyl)-3-iodo-L-tyrosine	ChEBI
(2S)-2-Amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoate	Generator
3,3'-Diiodothyronine, (L)-isomer, 125I-labeled	MeSH
3,3'-Diiodothyronine	MeSH
3,3'-T2	MeSH
3,3'-Diiodothyronine, (L)-isomer	MeSH
3,3'-Diiodothyronine, (DL)-isomer	MeSH

Chemical Formula

C₁₅H₁₃I₂NO₄

Average Mass

525.0770 Da

Monoisotopic Mass

524.89339 Da

IUPAC Name

(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoic acid

Traditional Name

3,3'-diiodo-L-thyronine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H13I2NO4/c16-10-7-9(2-3-13(10)19)22-14-4-1-8(5-11(14)17)6-12(18)15(20)21/h1-5,7,12,19H,6,18H2,(H,20,21)/t12-/m0/s1

InChI Key

CPCJBZABTUOGNM-LBPRGKRZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Homo sapiens	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
2-iodophenol
2-halophenol
Phenol ether
Iodobenzene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Amino acid
Ether
Carboxylic acid
Monocarboxylic acid or derivatives
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

3,3'-diiodothyronine (CHEBI:45698 )

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	0.46	ALOGPS
logP	1.87	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	0.75	ChemAxon
pKa (Strongest Basic)	9.5	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	100.06 m³·mol⁻¹	ChemAxon
Polarizability	38.51 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

Not Available

METLIN ID

Not Available

PubChem Compound

107564

PDB ID

Not Available

ChEBI ID

45698

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,3'-diiodo-l-thyronine (NP0299675)

MOL for NP0299675 (3,3'-diiodo-l-thyronine)

3D MOL for NP0299675 (3,3'-diiodo-l-thyronine)

3D SDF for NP0299675 (3,3'-diiodo-l-thyronine)

3D-SDF for NP0299675 (3,3'-diiodo-l-thyronine)

PDB for NP0299675 (3,3'-diiodo-l-thyronine)

3D PDB for NP0299675 (3,3'-diiodo-l-thyronine)

SMILES for NP0299675 (3,3'-diiodo-l-thyronine)

INCHI for NP0299675 (3,3'-diiodo-l-thyronine)

Structure for NP0299675 (3,3'-diiodo-l-thyronine)

3D Structure for NP0299675 (3,3'-diiodo-l-thyronine)