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5,10-Methylenetetrahydrofolate

PubChem CID
135398652
Structure
5,10-Methylenetetrahydrofolate_small.png
5,10-Methylenetetrahydrofolate_3D_Structure.png
Molecular Formula
Synonyms
  • 5,10-methylene-THF
  • 5,10-methylenetetrahydrofolate
  • SCHEMBL258730
  • 5,10-Methylene-6-Hydrofolate
  • N5>,N10-methylenetetrahydrofolate
Molecular Weight
457.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2019-01-15
  • Modify:
    2025-01-11
Description
5,10-Methylene-THF is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
5,10-Methylene-THF is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
5,10-Methylenetetrahydrofolate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[4-[(6aR)-3-amino-1-oxo-2,5,6,6a,7,9-hexahydroimidazo[1,5-f]pteridin-8-yl]benzoyl]amino]pentanedioic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

QYNUQALWYRSVHF-PZORYLMUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C1[C@@H]2CN(CN2C3=C(N1)N=C(NC3=O)N)C4=CC=C(C=C4)C(=O)NC(CCC(=O)O)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H23N7O6
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

31690-11-6

2.3.2 HMDB ID

2.3.3 KEGG ID

2.3.4 PharmGKB ID

2.3.5 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5,10-methylene-5,6,7,8-tetrahydrofolate
  • 5,10-methylenetetrahydrofolate
  • 5,10-methylenetetrahydrofolate monohydrochloride, (L-Glu)-isomer
  • 5,10-methylenetetrahydrofolate, (D-Glu)-isomer
  • 5,10-methylenetetrahydrofolate, (L-Glu)-(S)-isomer
  • 5,10-methylenetetrahydrofolic acid
  • CH2H4fol
  • CH2H4folate
  • N5,N10-methylene-5,6,7,8-tetrahydrofolic acid
  • tetrahydromethylenefolate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
457.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
457.17098148 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
457.17098148 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
190 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
33
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
911
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
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 2019.01.04)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

5 Chemical Vendors

6 Food Additives and Ingredients

6.1 Associated Foods

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Cellular Locations

Mitochondria

7.1.2 Metabolite Pathways

7.2 Biochemical Reactions

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Chemical Co-Occurrences in Literature

8.4 Chemical-Gene Co-Occurrences in Literature

8.5 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

10 Interactions and Pathways

10.1 Pathways

11 Taxonomy

Zebrafish Pathway Metabolite MetFrag Local CSV (Beta) | DOI:10.5281/zenodo.3457553

12 Classification

12.1 MeSH Tree

13 Information Sources

  1. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  2. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  3. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    5,10-Methylenetetrahydrofolate
  4. FooDB
    LICENSE
    FooDB 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 (FooDB) and the original publication.
    https://foodb.ca/about
    5,10-Methylenetetrahydrofolic acid
    https://foodb.ca/compounds/FDB022675
  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. 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
  7. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
    5,10-methylenetetrahydrofolate
    https://www.pharmgkb.org/chemical/PA166179139
  8. Wikipedia
  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
    5,10-methylenetetrahydrofolic acid
    https://www.ncbi.nlm.nih.gov/mesh/67013123
  11. PATENTSCOPE (WIPO)
CONTENTS