Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 5,10-Methylenetetrahydrofolate: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 18:25, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464482216 of page 5,10-Methylenetetrahydrofolate for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 10:09, 31 December 2024 edit YuniToumei (talk | contribs)Extended confirmed users1,734 edits add hatnote: distinguish from 5,10-Methenyltetrahydrofolate based on similar names 
Line 1: Line 1:
{{distinguish|5,10-Methenyltetrahydrofolate}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 443353978 | verifiedrevid = 477223777
|ImageFile=5,10-methylenetetrahydrofolic acid.svg | ImageFile=5,10-methylenetetrahydrofolic acid.svg
|ImageSize= | ImageSize=
|IUPACName= ''N''-pteridin-8(9''H'')-yl)benzoyl]-<small>L</small>-glutamic acid | IUPACName= ''N''-pteridin-8(9''H'')-yl)benzoyl]-<small>L</small>-glutamic acid
|OtherNames=5,10-CH<sub>2</sub>-THF,<br>MTHF | OtherNames=5,10-CH<sub>2</sub>-THF,<br>MTHF
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 97272 | ChemSpiderID = 97272
| InChI = 1/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-/m0/s1 | InChI = 1/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-/m0/s1
Line 17: Line 18:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QYNUQALWYRSVHF-ABLWVSNPSA-N | StdInChIKey = QYNUQALWYRSVHF-ABLWVSNPSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 3432-99-3 --> | CASNo=3432-99-3
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=108194
| UNII = 0SXY5ET48B
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | PubChem=108194
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 20502 | ChEBI = 20502
| SMILES = O=C(O)(NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)/N=C(/N)NC=2NC3)C4)CCC(=O)O | SMILES = O=C(O)(NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)/N=C(/N)NC=2NC3)C4)CCC(=O)O
| MeSHName=5,10-methylenetetrahydrofolate | MeSHName=5,10-methylenetetrahydrofolate
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>20</sub>H<sub>23</sub>N<sub>7</sub>O<sub>6</sub> | Formula=C<sub>20</sub>H<sub>23</sub>N<sub>7</sub>O<sub>6</sub>
| MolarMass=457.44 g/mol | MolarMass=457.44 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}

'''5,10-Methylenetetrahydrofolate''' ('''N5,N10-Methylenetetrahydrofolate; 5,10-CH<sub>2</sub>-THF''') is cofactor in several biochemical reactions. It exists in nature as the ] -5,10-methylene-THF.

As an intermediate in one-carbon metabolism, 5,10-CH<sub>2</sub>-THF converts to ], ], and methenyltetrahydrofolate. It is ] for the ] ] (MTHFR)<ref name="entrez">{{cite web | title = Entrez Gene: MTHFR methylenetetrahydrofolate reductase (NAD(P)H)| url = https://www.ncbi.nlm.nih.gov/sites/entrez?Db=gene&Cmd=ShowDetailView&TermToSearch=4524}}</ref><ref name="pmid10720211">{{cite journal| vauthors=Födinger M, Hörl WH, Sunder-Plassmann G| title=Molecular biology of 5,10-methylenetetrahydrofolate reductase. | journal=J Nephrol | year= 2000 | volume= 13 | issue= 1 | pages= 20–33 | pmid=10720211 }}</ref> It is mainly produced by the reaction of ] with serine, catalyzed by the enzyme ].

==Selected functions==
===Formaldehyde equivalent===
Methylenetetrahydrofolate is a source of the equivalent of formaldehyde or CH<sub>2</sub><sup>2+</sup> in biosyntheses.

Methylenetetrahydrofolate is also an intermediate in the detoxification of ].<ref>{{cite journal|author1=Marx, C. J. |author2=Chistoserdova, L. |author3=Lidstrom, M. E.|year=2003|title=Formaldehyde-detoxifying role of the tetrahydromethanopterin-linked pathway in ''Methylobacterium extorquens'' AM1|journal=J. Bacteriol.|volume=185|issue=24|pages=7160–8|pmid=14645276|pmc=296243|doi=10.1128/jb.185.23.7160-7168.2003}}</ref>

===Pyrimidine biosynthesis===
It is the one-carbon donor for ], for methylation of 2-deoxy-uridine-5-monophosphate (]) to 2-deoxy-thymidine-5-monophosphate (]). The ] is necessary for the ] of ] and is the C1-donor in the reactions catalyzed by TS and ].

===Biomodulator===
-5,10-methylene-THF is a biomodulator that has proven to enhance the desired cytotoxic antitumor effect of ] (5-FU) and can bypass the metabolic pathway required by other folates (such as ]) to achieve necessary activation.<ref>{{Cite journal|last=Danenberg|first=Peter V.|last2=Gustavsson|first2=Bengt|last3=Johnston|first3=Patrick|last4=Lindberg|first4=Per|last5=Moser|first5=Rudolf|last6=Odin|first6=Elisabeth|last7=Peters|first7=Godefridus J.|last8=Petrelli|first8=Nicholas|date=2016-10-01|title=Folates as adjuvants to anticancer agents: Chemical rationale and mechanism of action|journal=Critical Reviews in Oncology/Hematology|volume=106|pages=118–131|doi=10.1016/j.critrevonc.2016.08.001|issn=1879-0461|pmid=27637357|doi-access=free}}</ref> The active metabolite is being evaluated in clinical trials for patients with colorectal cancer in combination with 5-FU.

]. ]: 5-methyltetrahydrofolate; 5,10-methylenetetrahydrofolate; ]: Bcl-2-associated X protein; ]: betaine-homocysteine S-methyltransferase; ]: cystathionine beta synthase; ]: cystathionine gamma-lyase; ]: dihydrofolate (vitamin B9); ]: dimethylglycine; ]: thymidine monophosphate; ]: deoxyuridine monophosphate; ] flavine adenine dicucleotide; ]: 10-formyltetrahydrofolate; ]: methionine synthase; ]: methylenetetrahydrofolate reductase; ]: S-adenosyl-L-homocysteine; ]: S-adenosyl-L-methionine; ]: tetrahydrofolate.]]
{{clear|left}}

==See also==
* ]

==References==
{{reflist|30em}}
{{Enzyme cofactors}}
{{Vitamin}}

{{DEFAULTSORT:Methylenetetrahydrofolate, 5, 10-}}
]
]