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3,5-Diiodothyronine

PubChem CID
123675
Structure
3,5-Diiodothyronine_small.png
3,5-Diiodothyronine_3D_Structure.png
Molecular Formula
Synonyms
  • 3,5-Diiodothyronine
  • 3,5-Diiodo-DL-thyronine
  • 534-51-0
  • DL-3,5-Diiodothyronine
  • Diiodothyronine
Molecular Weight
525.08 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
3,5-Diiodothyronine is an organooxygen compound and an organonitrogen compound. It is functionally related to an alpha-amino acid.
See also: 3,5-Diiodothyronine, D- (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3,5-Diiodothyronine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ZHSOTLOTTDYIIK-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC(=CC=C1O)OC2=C(C=C(C=C2I)CC(C(=O)O)N)I
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H13I2NO4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1041-01-6
5563-89-3

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 NSC Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3,5-diiodo-DL-thyronine
  • 3,5-diiodo-L-thyronine
  • 3,5-diiodothyronine
  • 3,5-diiodothyronine, (DL)-isomer
  • 3,5-diiodothyronine, (L)-isomer
  • 3,5-T2

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
525.08 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
524.89340 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
524.89340 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
92.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
365
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Collision Cross Section

198.2 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

186.44 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CD3OD
pH
7.00
Shifts [ppm]:Intensity
6.68:52.61, 3.77:13.74, 3.76:11.85, 3.22:8.53, 3.78:13.27, 3.78:11.37, 6.58:36.97, 3.24:7.11, 3.21:8.06, 6.70:36.02, 2.97:7.58, 6.60:50.24, 3.23:6.64, 2.99:7.58, 7.87:100.00, 3.01:9.48, 3.00:9.00
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2 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CD3OD
pH
7.00
Shifts [ppm] (F2:F1):Intensity
6.69:116.86:1.00, 6.60:117.19:0.97, 3.23:36.35:0.17, 3.77:57.16:0.56, 7.88:142.40:0.51, 2.99:36.35:0.21
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4.3 Mass Spectrometry

4.3.1 GC-MS

Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 MS-MS

1 of 2
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

525.96 100

525.48 30.68

526.62 7.64

480.12 7.56

480.54 2.34

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 2
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

480.0 100

525.96 81.44

382.2 29.87

508.98 14.45

479.46 10.44

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad

4.3.3 LC-MS

1 of 35
View All
Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
80
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
7.539 min
Precursor m/z
523.8861
Precursor Adduct
[M-H]-
Top 5 Peaks
126.905 999
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License
dl-de/by-2-0
2 of 35
View All
Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
50
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
7.539 min
Precursor m/z
523.8861
Precursor Adduct
[M-H]-
Top 5 Peaks
126.9046 999
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License
dl-de/by-2-0

4.3.4 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
525.901
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

479.891632 100

352.989441 45.15

525.892639 37.75

324.969818 28.68

381.966156 26.32

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2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
523.886
Instrument
qTof
Ionization Mode
negative
Top 5 Peaks

126.903427 100

523.889832 23.99

506.862885 11.28

506.869232 10.38

506.853333 8.86

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4.4 IR Spectra

4.4.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Biomarker Information

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Tissue Locations

Brain

8.1.2 Cellular Locations

Cytoplasm

8.2 Biochemical Reactions

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (94.2%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 52 reports by companies from 3 notifications to the ECHA C&L Inventory.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (94.2%)

9.2 Regulatory Information

REACH Registered Substance

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

13.2 Pathways

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 ChEMBL Target Tree

16.5 UN GHS Classification

16.6 NORMAN Suspect List Exchange Classification

16.7 CCSBase Classification

16.8 EPA DSSTox Classification

16.9 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  8. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  9. ChEBI
  10. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  11. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  12. SpectraBase
    D-3-[3,5-diiodo-4-(p-hydroxyphenoxy)phenyl]alanine
    https://spectrabase.com/spectrum/CtALNrtBRx6
    D-3-[3,5-DIIODO-4-(p-HYDROXYPHENOXY)PHENYL]ALANINE
    https://spectrabase.com/spectrum/AdBRC5J9hiy
    D-3-[3,5-DIIODO-4-(p-HYDROXYPHENOXY)PHENYL]ALANINE
    https://spectrabase.com/spectrum/4pBjh4NFlFj
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  15. MassBank Europe
  16. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  17. Metabolomics Workbench
  18. Natural Product Activity and Species Source (NPASS)
    2-Ammonio-3-[4-(4-Hydroxyphenoxy)-3,5-Diiodophenyl]Propanoate
    https://bidd.group/NPASS/compound.php?compoundID=NPC318984
  19. Springer Nature
  20. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  21. Wikidata
  22. Wikipedia
  23. PubChem
  24. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  25. GHS Classification (UNECE)
  26. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  27. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  28. PATENTSCOPE (WIPO)
CONTENTS