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5-Carboxy-2'-deoxyuridine

PubChem CID
10492375
Structure
5-Carboxy-2'-deoxyuridine_small.png
5-Carboxy-2'-deoxyuridine_3D_Structure.png
Molecular Formula
Synonyms
  • 5-Carboxy-2'-deoxyuridine
  • 14599-46-3
  • 2'-Deoxy-5-carboxyuridine
  • TP4HBV9HED
  • 5-Pyrimidinecarboxylic acid, 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxo-
Molecular Weight
272.21 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-11
Description
5-carboxy-2'-deoxyuridine is a nucleoside analogue that is 2'-deoxyuridine in which the hydrogen at position 5 on the uracil ring is replaced by a carboxy group. It has a role as a Mycoplasma genitalium metabolite and a drug metabolite. It is a nucleoside analogue, a pyrimidine 2'-deoxyribonucleoside and an aromatic carboxylic acid. It is functionally related to a uracil.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
5-Carboxy-2'-deoxyuridine.png

1.2 3D Conformer

2 Biologic Description

IUPAC Condensed
ac5Ura-dRibf
Sequence
N
HELM
RNA1{[dR]([*n1cc(c(=O)[nH]c1=O)C(=O)O |$_R1;;;;;;;;;;;$|])}$$$$

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidine-5-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C10H12N2O7/c13-3-6-5(14)1-7(19-6)12-2-4(9(16)17)8(15)11-10(12)18/h2,5-7,13-14H,1,3H2,(H,16,17)(H,11,15,18)/t5-,6+,7+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

GAGYTXTVUMXAOC-RRKCRQDMSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)C(=O)O)CO)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C10H12N2O7
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 UNII

3.3.3 ChEBI ID

3.3.4 Nikkaji Number

3.3.5 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • 2'-deoxy-5-carboxyuridine
  • 5-carboxy-2'-deoxyuridine

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
272.21 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-1.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
272.06445073 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
272.06445073 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
136 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
461
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
3
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 2021.10.14)

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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7 Chemical Vendors

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Chemical Co-Occurrences in Literature

8.5 Chemical-Gene Co-Occurrences in Literature

8.6 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Classification

10.1 MeSH Tree

10.2 ChEBI Ontology

10.3 ChemIDplus

10.4 MolGenie Organic Chemistry Ontology

11 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/
    1-(2-Deoxy-β-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinecarboxylic acid
    https://commonchemistry.cas.org/detail?cas_rn=14599-46-3
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. 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
  4. ChEBI
  5. Japan Chemical Substance Dictionary (Nikkaji)
  6. SpectraBase
  7. Springer Nature
  8. Wikidata
  9. PubChem
  10. 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
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  12. PATENTSCOPE (WIPO)
CONTENTS