An official website of the United States government

5-Diazouracil

PubChem CID
73266
Structure
5-Diazouracil_small.png
5-Diazouracil_3D_Structure.png
Molecular Formula
Synonyms
  • 5-Diazouracil
  • 2435-76-9
  • Diazouracil
  • Uracil, 5-diazo-
  • 2,6-Dioxo-5-diazopyrimidine
Molecular Weight
138.08 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-02-01
Description
5-diazouracil is a diazo compound. It is functionally related to a uracil.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
5-Diazouracil.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-diazonio-6-oxo-1H-pyrimidin-2-olate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C4H2N4O2/c5-8-2-1-6-4(10)7-3(2)9/h1H,(H-,6,7,9,10)
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

XFLJNCDBYCPPTE-UHFFFAOYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

C1=C(C(=O)NC(=N1)[O-])[N+]#N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C4H2N4O2
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

2435-76-9

2.3.2 Deprecated CAS

3240-69-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Nikkaji Number

2.3.11 NSC Number

2.3.12 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

5-diazouracil

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
138.08 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
0.9
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
138.01777532 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
138.01777532 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
92.7 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
281
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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
0
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 2011.04.04)

3.2 Experimental Properties

3.2.1 Physical Description

Solid; Sensitive to light, air, and temperature; [Merck Index]

3.3 Chemical Classes

Other Uses -> Biochemical Research

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
NIST Number
127447
Library
Main library
Total Peaks
85
m/z Top Peak
67
m/z 2nd Highest
138
m/z 3rd Highest
43
Thumbnail
Thumbnail
2 of 2
NIST Number
130059
Library
Replicate library
Total Peaks
19
m/z Top Peak
138
m/z 2nd Highest
67
m/z 3rd Highest
43
Thumbnail
Thumbnail

6 Chemical Vendors

7 Use and Manufacturing

7.1 Uses

Sources/Uses
Used in cancer research; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

7.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
2,4(3H,5H)-Pyrimidinedione, 5-diazo-: INACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Flammable
Irritant
Signal
Danger
GHS Hazard Statements

H242 (100%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statement Codes

P210, P234, P235, P240, P261, P264, P270, P271, P280, P301+P317, P304+P340, P317, P330, P370+P378, P403, P410, P411, P420, and P501

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

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

8.1.2 Hazard Classes and Categories

Self-react. C (100%)

Acute Tox. 4 (100%)

Acute Tox. 4 (100%)

8.1.3 Hazards Summary

Intraperitoneal LD50 (mouse) = 30.8 mg/kg; [RTECS] A study from 1973 reported that 5-20 mg/kg administered on day 10 produced embryo lethality but no teratogenicity in mice; [Shepard's Catalog of Teratogenic Agents] May cause irritation; [Sigma-Aldrich MSDS]

9 Toxicity

9.1 Toxicological Information

9.1.1 Acute Effects

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 Chemical Co-Occurrences in Patents

11.3 Chemical-Disease Co-Occurrences in Patents

11.4 Chemical-Gene Co-Occurrences in Patents

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 ChemIDplus

13.4 ChEMBL Target Tree

13.5 UN GHS Classification

13.6 NORMAN Suspect List Exchange Classification

13.7 EPA DSSTox Classification

13.8 EPA TSCA and CDR Classification

13.9 EPA Substance Registry Services Tree

13.10 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. ChEBI
  2. 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
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. 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
  5. EPA Chemicals under the TSCA
    2,4(3H,5H)-Pyrimidinedione, 5-diazo-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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
  8. 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
  9. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  10. 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
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  13. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  14. Springer Nature
  15. Wikidata
  16. PubChem
  17. 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
  18. GHS Classification (UNECE)
  19. 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/
  20. EPA Substance Registry Services
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS