| Revision as of 12:39, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464794145 of page Tetrahydrofolic_acid for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 23:07, 4 November 2023 edit Neko-chan (talk | contribs)Extended confirmed users, New page reviewers, Rollbackers20,609 edits →top: editing chem and a citeTags: Mobile edit Mobile app edit Android app edit |
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{{distinguish|Tetrahydrofuran}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{Chembox |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 450474998 |
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| verifiedrevid = 470604221 |
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| ImageFile = Tetrahydrofolic acid.svg |
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| ImageFile = Tetrahydrofolic acid.svg |
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| ImageSize = 250px |
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| ImageSize = 260px |
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| ImageAlt = Skeletal formula of tetrahydrofolic acid |
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| IUPACName = (2''S'')-2-{methyl}amino)phenyl]formamido}pentanedioic acid |
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| ImageFile1 = Tetrahydrofolic-acid-3D-spacefill.png |
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| ImageSize1 = 250 |
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| ImageAlt1 = Space-filling model of the tetrahydrofolic acid molecule |
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| IUPACName = ''N''-methyl}amino)benzoyl]-<small>L</small>-glutamic acid |
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| SystematicName = (2''S'')-2-methyl}amino)benzamido]pentanedioic acid |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| IUPHAR_ligand = 4675 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 82572 |
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| ChemSpiderID = 82572 |
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| InChI = 1/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1 |
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| InChI = 1/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MSTNYGQPCMXVAQ-KIYNQFGBSA-N |
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| StdInChIKey = MSTNYGQPCMXVAQ-KIYNQFGBSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 29347-89-5 --> |
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| CASNo = 135-16-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 91443 |
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| UNII = 43ZWB253H4 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| PubChem = 91443 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00116 |
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| DrugBank = DB00116 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C00101 |
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| KEGG = C00101 |
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| 3DMet = B04806 |
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| Beilstein = 101189 |
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| SMILES = O=C(O)(NC(=O)c1ccc(cc1)NCC3N/C2=C(/N/C(=N\C2=O)N)NC3)CCC(=O)O |
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| SMILES = O=C(O)(NC(=O)c1ccc(cc1)NCC3N/C2=C(/N/C(=N\C2=O)N)NC3)CCC(=O)O |
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| MeSHName = 5,6,7,8-tetrahydrofolic+acid |
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| MeSHName = 5,6,7,8-tetrahydrofolic+acid |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = {{chem2|C19H23N7O6}} |
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| Formula = C<sub>19</sub>H<sub>23</sub>N<sub>7</sub>O<sub>6</sub> |
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| MolarMass = 445.43 g/mol |
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| MolarMass = 445.43 g/mol |
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| Appearance = |
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| Density = |
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| MeltingPt = |
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| MeltingPtC = 250 |
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| BoilingPt = |
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| pKa = 3.51 |
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| Solubility = 0.27 g/L |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| Solubility = |
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}} |
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}} |
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'''Tetrahydrofolic acid''' ('''THFA'''), or '''tetrahydrofolate''', is a ] derivative. |
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==Metabolism== |
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===Human synthesis=== |
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Tetrahydrofolic acid is produced from ] by ]. This reaction is inhibited by ].<ref>{{Cite journal|last1=Rajagopalan|first1=P. T. Ravi|last2=Zhang|first2=Zhiquan|last3=McCourt|first3=Lynn|last4=Dwyer|first4=Mary|last5=Benkovic|first5=Stephen J.|last6=Hammes|first6=Gordon G.|date=2002-10-15|title=Interaction of dihydrofolate reductase with methotrexate: Ensemble and single-molecule kinetics|journal=Proceedings of the National Academy of Sciences|language=en|volume=99|issue=21|pages=13481–13486|doi=10.1073/pnas.172501499|issn=0027-8424|pmc=129699|pmid=12359872|bibcode=2002PNAS...9913481R|doi-access=free}}</ref> |
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It is converted into ] by ]. |
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===Bacterial synthesis=== |
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Many bacteria use ] to produce ], a molecule without function in humans. This makes it a useful target for ] antibiotics, which compete with the ] precursor. |
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] |
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{{clear left}} |
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==Functions== |
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Tetrahydrofolic acid is a ] in many reactions, especially in the synthesis (or anabolism) of ]s and ]s. In addition, it serves as a carrier molecule for single-carbon moieties, that is, groups containing one carbon atom e.g. ], ], ], ], or formimino. When combined with one such single-carbon moiety as in ], it acts as a donor of a group with one carbon atom. Tetrahydrofolate gets this extra carbon atom by sequestering ] produced in other processes. These single-carbon moieties are important in the formation of precursors for DNA synthesis. A shortage in tetrahydrofolic acid (FH4) can cause ].<ref>{{Cite web|date=2008-02-23|title=Biochemistry: The One-Carbon Pool: Folate and B12 Metabolism |url=https://liveonearth.livejournal.com/260487.html|archive-url=|archive-date=|access-date=2020-12-15|website=liveonearth.livejournal.com}}</ref><ref>{{Cite journal |last1=Yadav |first1=Manish K. |last2=Manoli |first2=Nandini M. |last3=Madhunapantula |first3=SubbaRao V. |date=2016-10-25 |editor-last=Roemer |editor-first=Klaus |title=Comparative Assessment of Vitamin-B12, Folic Acid and Homocysteine Levels in Relation to p53 Expression in Megaloblastic Anemia |journal=PLOS ONE |language=en |volume=11 |issue=10 |pages=e0164559 |doi=10.1371/journal.pone.0164559 |issn=1932-6203 |pmc=5079580 |pmid=27780269|bibcode=2016PLoSO..1164559Y |doi-access=free }}</ref><ref>{{Cite journal |last1=Aslinia |first1=F. |last2=Mazza |first2=J. J. |last3=Yale |first3=S. H. |date=2006-09-01 |title=Megaloblastic Anemia and Other Causes of Macrocytosis |journal=Clinical Medicine & Research |language=en |volume=4 |issue=3 |pages=236–241 |doi=10.3121/cmr.4.3.236 |issn=1539-4182 |pmc=1570488 |pmid=16988104}}</ref> |
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Methotrexate acts on dihydrofolate reductase, like ] or ], as an inhibitor and thus reduces the amount of tetrahydrofolate made. This may result in megaloblastic anemia. |
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Tetrahydrofolic acid is involved in the conversion of ] to ]; this may reduce the amount of ] available for decarboxylation and protein synthesis, and hence the urinary histamine and formiminoglutamic acid may be decreased.<ref>{{cite journal |vauthors=Dawson W, Maudsley DV, West GB |title=Histamine formation in guinea-pigs |journal=J. Physiol. |volume=181 |issue=4 |pages=801–9 |date=December 1965 |pmid=5881255 |pmc=1357684 |doi=10.1113/jphysiol.1965.sp007798 }}</ref> |
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<gallery> |
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Image:Dihydrofolic acid.svg|] |
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Image:5,10-methylenetetrahydrofolic acid.svg|] |
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Image:10-formyl-tetrahydrofolic acid.svg|] |
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</gallery> |
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== References == |
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{{reflist}} |
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==External links== |
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* in the ] |
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{{Enzyme cofactors}} |
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{{Authority control}} |
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{{DEFAULTSORT:Tetrahydrofolic Acid}} |
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] |
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] |