3,5-Diiodotyrosine

Identification

Name
3,5-Diiodotyrosine
Accession Number
DB03374  (EXPT03137)
Type
Small Molecule
Groups
Experimental
Description

A product from the iodination of MONOIODOTYROSINE. In the biosynthesis of thyroid hormones, diiodotyrosine residues are coupled with other monoiodotyrosine or diiodotyrosine residues to form T4 or T3 thyroid hormones (THYROXINE and TRIIODOTHYRONINE). [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
6L57Q44ZWW
CAS number
300-39-0
Weight
Average: 432.9816
Monoisotopic: 432.867179999
Chemical Formula
C9H9I2NO3
InChI Key
NYPYHUZRZVSYKL-ZETCQYMHSA-N
InChI
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
IUPAC Name
(2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid
SMILES
[H][C@](N)(CC1=CC(I)=C(O)C(I)=C1)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcAMP-dependent protein kinase inhibitor alphaNot AvailableHuman
UcAMP-dependent protein kinase catalytic subunit alphaNot AvailableHuman
UAlpha-amylase G-6Not AvailableBacillus halodurans (strain ATCC BAA-125 / DSM 18197 / FERM 7344 / JCM 9153 / C-125)
UTrypsin-1Not AvailableHuman
UNickel-binding periplasmic proteinNot AvailableEscherichia coli (strain K12)
UIodotyrosine dehalogenase 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Thyroid hormone synthesisMetabolic
Thyroid hormone synthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0003474
KEGG Compound
C01060
PubChem Compound
9305
PubChem Substance
46507686
ChemSpider
8946
ChEBI
15768
ChEMBL
CHEMBL1236469
HET
TYI
PDB Entries
1ctp / 1l0s / 2axe / 2c3v / 2d8o / 2d8p / 2d8w / 2d97 / 2d98 / 2noo
show 8 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility617 mg/L (at 25 °C)CRC HANDBOOK
Predicted Properties
PropertyValueSource
Water Solubility0.519 mg/mLALOGPS
logP-0.7ALOGPS
logP0.37ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)0.48ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.82 m3·mol-1ChemAxon
Polarizability29.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9138
Blood Brain Barrier-0.7811
Caco-2 permeable-0.5568
P-glycoprotein substrateNon-substrate0.6471
P-glycoprotein inhibitor INon-inhibitor0.9789
P-glycoprotein inhibitor IINon-inhibitor0.9962
Renal organic cation transporterNon-inhibitor0.922
CYP450 2C9 substrateNon-substrate0.8536
CYP450 2D6 substrateNon-substrate0.8758
CYP450 3A4 substrateNon-substrate0.7515
CYP450 1A2 substrateNon-inhibitor0.9044
CYP450 2C9 inhibitorNon-inhibitor0.9099
CYP450 2D6 inhibitorNon-inhibitor0.9465
CYP450 2C19 inhibitorNon-inhibitor0.9455
CYP450 3A4 inhibitorNon-inhibitor0.9077
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.955
Ames testNon AMES toxic0.804
CarcinogenicityNon-carcinogens0.9127
BiodegradationNot ready biodegradable0.9332
Rat acute toxicity2.6025 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9657
hERG inhibition (predictor II)Non-inhibitor0.9459
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-014i-1890000000-abcce0f0eb05b9c55156
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1890000000-abcce0f0eb05b9c55156
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0000900000-ae6a8b173bc71991a4ac
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-001i-0200900000-0ba2bdb29d10e206243b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-004i-0922200000-9937df05a2005a9dccdc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-004i-0911000000-7b8269ff37ddf87ca91e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-004i-0900000000-b8211c790d768a3d3ca4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001i-0000900000-22bf410c5cb442851336
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001r-0017900000-b678ad76193892db31d6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-000i-0049100000-d8fdce763cb949d3c346
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-01p9-0197000000-70418018a4eb3733c732
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-03di-0191000000-83c286061170a2257b7c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0000900000-ae6a8b173bc71991a4ac
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0200900000-10d7f46230d75a69ca8a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0922200000-9937df05a2005a9dccdc
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0911000000-7b8269ff37ddf87ca91e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-afdb17f670e1a6b9d237
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0000900000-22bf410c5cb442851336
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001r-0017900000-b678ad76193892db31d6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0049100000-d8fdce763cb949d3c346
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01p9-0197000000-1f8616e6ceeb67a66f5d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0191000000-83c286061170a2257b7c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03ei-2492000000-758324f5bb036f5e7439
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as tyrosine and derivatives. These 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
Phenylalanine and derivatives / Phenylpropanoic acids / Amphetamines and derivatives / L-alpha-amino acids / O-iodophenols / Aralkylamines / Iodobenzenes / Aryl iodides / Amino acids / Monocarboxylic acids and derivatives
show 7 more
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
show 23 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-tyrosine derivative, diiodotyrosine (CHEBI:15768) / Other amino acids (C01060)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein kinase a catalytic subunit binding
Specific Function
Extremely potent competitive inhibitor of cAMP-dependent protein kinase activity, this protein interacts with the catalytic subunit of the enzyme after the cAMP-induced dissociation of its regulato...
Gene Name
PKIA
Uniprot ID
P61925
Uniprot Name
cAMP-dependent protein kinase inhibitor alpha
Molecular Weight
7988.435 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Phosphorylates a large number of substrates in the cytoplasm and the nucleus. Regulates the abundance of compartmentalized pools of its regulatory subunits through phosphorylation of PJA2 which bin...
Gene Name
PRKACA
Uniprot ID
P17612
Uniprot Name
cAMP-dependent protein kinase catalytic subunit alpha
Molecular Weight
40589.38 Da
References
  1. 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]
Kind
Protein
Organism
Bacillus halodurans (strain ATCC BAA-125 / DSM 18197 / FERM 7344 / JCM 9153 / C-125)
Pharmacological action
Unknown
General Function
Starch binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q9KFR4
Uniprot Name
Alpha-amylase G-6
Molecular Weight
107161.875 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-1
Molecular Weight
26557.88 Da
References
  1. 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Transition metal ion binding
Specific Function
Involved in a nickel transport system, probably represents the nickel binder.
Gene Name
nikA
Uniprot ID
P33590
Uniprot Name
Nickel-binding periplasmic protein
Molecular Weight
58718.435 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Catalyzes the oxidative NADPH-dependent deiodination of monoiodotyrosine (L-MIT) or diiodotyrosine (L-DIT). Acts during the hydrolysis of thyroglobulin to liberate iodide, which can then reenter th...
Gene Name
IYD
Uniprot ID
Q6PHW0
Uniprot Name
Iodotyrosine deiodinase 1
Molecular Weight
33359.41 Da
References
  1. 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]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 07:15