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6,7-Dimethyl-8-ribityllumazine

PubChem CID
168989
Structure
6,7-Dimethyl-8-ribityllumazine_small.png
6,7-Dimethyl-8-ribityllumazine_3D_Structure.png
Molecular Formula
Synonyms
  • 6,7-Dimethyl-8-ribityllumazine
  • DMDRL
  • 2535-20-8
  • Russupteridine IV
  • 6,7-Dimethylribityl Lumazine
Molecular Weight
326.31 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
6,7-dimethyl-8-(1-D-ribityl)lumazine is the pteridine that is lumazine substituted with methyl groups at C-6 and -7 and with a 1-D-ribityl group on N-8. It has a role as an Escherichia coli metabolite and a cofactor. It is functionally related to a lumazine and a ribitol. It is a conjugate acid of a 6,7-dimethyl-8-(1-D-ribityl)lumazine(1-).
6,7-Dimethyl-8-(1-D-ribityl)lumazine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
6,7-Dimethyl-8-ribityllumazine has been reported in Eremothecium ashbyi and Eremothecium gossypii with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
6,7-Dimethyl-8-ribityllumazine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

6,7-dimethyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pteridine-2,4-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C13H18N4O6/c1-5-6(2)17(3-7(19)10(21)8(20)4-18)11-9(14-5)12(22)16-13(23)15-11/h7-8,10,18-21H,3-4H2,1-2H3,(H,16,22,23)/t7-,8+,10-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SXDXRJZUAJBNFL-XKSSXDPKSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=C(N(C2=NC(=O)NC(=O)C2=N1)C[C@@H]([C@@H]([C@@H](CO)O)O)O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C13H18N4O6
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

5118-16-1

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 HMDB ID

2.3.6 KEGG ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 Wikidata

2.3.10 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 6,7-dimethyl-8-(1'-D-ribityl)lumazine
  • 6,7-dimethyl-8-ribityllumazine
  • 6,7-dimethyl-8-ribityllumazine, (D)-isomer
  • 6,7-dimethyl-8-ribityllumazine, 14C-labeled
  • DMDRL

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
326.31 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-2.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
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
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
326.12263431 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
326.12263431 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
155 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
626
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)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 LogP

-3.145

5 Chemical Vendors

6 Pharmacology and Biochemistry

6.1 Human Metabolite Information

6.1.1 Metabolite Pathways

6.2 Biochemical Reactions

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

7.4 Chemical-Gene Co-Occurrences in Literature

7.5 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

8.3 Chemical Co-Occurrences in Patents

8.4 Chemical-Disease Co-Occurrences in Patents

8.5 Chemical-Gene Co-Occurrences in Patents

9 Interactions and Pathways

9.1 Protein Bound 3D Structures

9.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

9.2 Pathways

10 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

11 Classification

11.1 MeSH Tree

11.2 ChEBI Ontology

11.3 ChemIDplus

11.4 EPA DSSTox Classification

11.5 LOTUS Tree

11.6 MolGenie Organic Chemistry Ontology

12 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. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
  5. 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
    6,7-Dimethyl-8-(1-D-ribityl)lumazine
    http://www.hmdb.ca/metabolites/HMDB0003826
  6. ChEBI
  7. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  8. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    6,7-Dimethyl-8-ribityllumazine
    https://www.wikidata.org/wiki/Q4641523
  9. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
    6,7-Dimethyl-8-(1-D-ribityl)lumazine
    https://www.ymdb.ca/compounds/YMDB00766
  10. Natural Product Activity and Species Source (NPASS)
  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. Metabolomics Workbench
  14. Protein Data Bank in Europe (PDBe)
  15. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  16. Wikidata
    6,7-dimethyl-8-(1-D-ribityl)lumazine
    https://www.wikidata.org/wiki/Q4641523
  17. Wikipedia
  18. PubChem
  19. 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
    6,7-dimethyl-8-ribityllumazine
    https://www.ncbi.nlm.nih.gov/mesh/67001061
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
  22. NCBI
CONTENTS