Showing Compound 3,5-Diiodo-L-tyrosine (FDB023181)

Record Information

Version

1.0

Creation date

2011-09-21 00:25:51 UTC

Update date

2015-10-09 22:33:06 UTC

Primary ID

FDB023181

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3,5-Diiodo-L-tyrosine

Description

3,5-Diiodo-L-tyrosine, also known as diiy or DIT, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 3,5-Diiodo-L-tyrosine is a very strong basic compound (based on its pKa). 3,5-Diiodo-L-tyrosine exists in all living organisms, ranging from bacteria to humans.

CAS Number

300-39-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid	ChEBI
3,5-Diiodotyrosine	ChEBI
Diiodotyrosine	ChEBI
DiIY	ChEBI
DIT	ChEBI
L-3,5-Diiodotyrosine	ChEBI
L-Diiodotyrosine	ChEBI
(2S)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoate	Generator
3,5-Diiodotyrocine	HMDB
3,5-Iodo-L-tyrosine	HMDB
3,5-L-Diiodotyrosine	HMDB
4-Hydroxy-3,5-diiodophenylalanine	HMDB
Iodogorgoic acid	HMDB
Acid, iodogorgoic	HMDB
(2S)-2-amino-3-(4-Hydroxy-3,5-diiodophenyl)propanoate	Generator
(2S)-2-amino-3-(4-Hydroxy-3,5-diiodophenyl)propanoic acid	ChEBI
L-3,5-DiioDOTyrosine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.52 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	0.37	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	0.48	ChemAxon
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.82 m³·mol⁻¹	ChemAxon
Polarizability	29.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H9I2NO3

IUPAC name

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

InChI Identifier

InChI=1S/C9H9I2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)/t7-/m0/s1

InChI Key

NYPYHUZRZVSYKL-ZETCQYMHSA-N

Isomeric SMILES

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

Average Molecular Weight

432.9816

Monoisotopic Molecular Weight

432.867179999

Classification

Description

Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Alpha-amino acid
L-alpha-amino acid
2-iodophenol
2-halophenol
Aralkylamine
Halobenzene
Phenol
Iodobenzene
Aryl iodide
Monocyclic benzene moiety
Benzenoid
Aryl halide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organoiodide
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:15768 )
L-tyrosine derivative (CHEBI:15768 )
diiodotyrosine (CHEBI:15768 )
Other amino acids (C01060 )

Ontology

Physiological effect

Health effect:

Health condition:

Renal and urinary disorders:

Chronic kidney disease

Endocrine disorders:

Hyperthyroidism

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	3,5-Diiodo-L-tyrosine, 3 TMS, GC-MS Spectrum	splash10-014i-1890000000-abcce0f0eb05b9c55156	Spectrum
GC-MS	3,5-Diiodo-L-tyrosine, non-derivatized, GC-MS Spectrum	splash10-014i-1890000000-abcce0f0eb05b9c55156	Spectrum
Predicted GC-MS	3,5-Diiodo-L-tyrosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052r-3009200000-5d38989f994f24e925d9	Spectrum
Predicted GC-MS	3,5-Diiodo-L-tyrosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0avr-9302530000-665bd4d1e52bd2a50a9c	Spectrum
Predicted GC-MS	3,5-Diiodo-L-tyrosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0000900000-ae6a8b173bc71991a4ac	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0200900000-0ba2bdb29d10e206243b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-0922200000-9937df05a2005a9dccdc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-0911000000-7b8269ff37ddf87ca91e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-0900000000-b8211c790d768a3d3ca4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0000900000-22bf410c5cb442851336	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001r-0017900000-b678ad76193892db31d6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-0049100000-d8fdce763cb949d3c346	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-01p9-0197000000-70418018a4eb3733c732	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-03di-0191000000-83c286061170a2257b7c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03ei-2492000000-758324f5bb036f5e7439	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0000900000-ae6a8b173bc71991a4ac	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0200900000-10d7f46230d75a69ca8a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0922200000-9937df05a2005a9dccdc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0911000000-7b8269ff37ddf87ca91e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-afdb17f670e1a6b9d237	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0000900000-22bf410c5cb442851336	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001r-0017900000-b678ad76193892db31d6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0049100000-d8fdce763cb949d3c346	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-0009600000-f51bf251094f35e469e4	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0009000000-68414bff61726c960b96	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-0009000000-7623a376300575297b5f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0001900000-dce45ddc0efcbd787f4a	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2006900000-6fb8e76ede4b97e18a40	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9036000000-4a8ca25b7e8f09067ce0	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Spectrum