Tetrahydrofolic acid (CHEM022060)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:18:48 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022060
Identification
Common NameTetrahydrofolic acid
ClassSmall Molecule
DescriptionTetrahydrofolic acid, also known as tetrahydrofolic acid, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. Tetrahydrofolic acid is possibly soluble (in water) and a strong basic compound (based on its pKa). Tetrahydrofolic acid exists in all eukaryotes, ranging from yeast to humans. Tetrahydrofolic acid participates in a number of enzymatic reactions, within cattle. In particular, Tetrahydrofolic acid can be converted into dihydrofolic acid through its interaction with the enzyme dihydrofolate reductase. In addition, Tetrahydrofolic acid and formic acid can be converted into 10-formyltetrahydrofolic acid; which is mediated by the enzyme C-1-tetrahydrofolic acid synthase, cytoplasmic. In cattle, tetrahydrofolic acid is involved in the metabolic pathway called the folate metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TetrahydrofolateGenerator
(6S)-TetrahydrofolateHMDB
(6S)-Tetrahydrofolic acidHMDB
5,6,7,8-TetrahydrofolateHMDB
5,6,7,8-Tetrahydrofolic acidHMDB
Tetra-H-folateHMDB
TetrahydrafolateHMDB
Tetrahydropteroyl mono-L-glutamateHMDB
TetrahydropteroylglutamateHMDB
Chemical FormulaC19H23N7O6
Average Molecular Mass445.429 g/mol
Monoisotopic Mass445.171 g/mol
CAS Registry Number135-16-0
IUPAC Name2-{[4-({[(6S)-4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
Traditional Name2-{[4-({[(6S)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
SMILESNC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1
InChI IdentifierInChI=1S/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
InChI KeyMSTNYGQPCMXVAQ-PXYINDEMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • Purinone
  • 6-oxopurine
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP-0.96ALOGPS
logP-3.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)2.04ChemAxon
pKa (Strongest Basic)5.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area208.26 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity132.4 m³·mol⁻¹ChemAxon
Polarizability44.57 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uka-4676900000-780e78301e85c240ab73Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-1311190000-af98cc8be4da08f9b782Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-7796610000-0937514a7f23431b726eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0nor-3269210000-20105ed6a7a6e24e2441Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kr-1935200000-a9449c19c1ae3b0d70daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0032-0431900000-ff1f3948e47561161293Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0952300000-ed9d84bc39d490f6210eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0920000000-0d0efcb6c323340d20b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0001900000-abb4cec0eb79b0bd2de1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4l-2356900000-2fd17d2f587bbd5e882cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9441000000-8c630c7a3633467d6bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0080900000-73480c24ce118e5e02f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0491100000-0b5df4d0f168f8f15275Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-0962000000-9a988cf519f340f5d7cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005c-0002900000-9587282a39f915386f95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zi3-2807900000-28355749389d1e225f7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3911000000-e7b1ccb0c9f2d7c8269aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001846
FooDB IDFDB022705
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID33856
BioCyc IDTHF
METLIN ID714
PDB IDNot Available
Wikipedia LinkTetrahydrofolic acid
Chemspider ID82572
ChEBI ID20506
PubChem Compound ID91443
Kegg Compound IDC00101
YMDB IDYMDB00139
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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8. Siega-Riz AM, Savitz DA, Zeisel SH, Thorp JM, Herring A: Second trimester folate status and preterm birth. Am J Obstet Gynecol. 2004 Dec;191(6):1851-7.
9. Taber LD, O'Brien P, Bowsher RR, Sportsman JR: Competitive particle concentration fluorescence immunoassay for measuring 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (lometrexol) in serum. Clin Chem. 1991 Feb;37(2):254-60.
10. Mattson MP: Gene-diet interactions in brain aging and neurodegenerative disorders. Ann Intern Med. 2003 Sep 2;139(5 Pt 2):441-4.
11. Dietrich M, Brown CJ, Block G: The effect of folate fortification of cereal-grain products on blood folate status, dietary folate intake, and dietary folate sources among adult non-supplement users in the United States. J Am Coll Nutr. 2005 Aug;24(4):266-74.
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14. Makino Y, Nagano M, Tamura K, Kawarabayashi T: Pregnancy complicated with pure red cell aplasia: a case report. J Perinat Med. 2003;31(6):530-4.
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16. Pufulete M, Al-Ghnaniem R, Khushal A, Appleby P, Harris N, Gout S, Emery PW, Sanders TA: Effect of folic acid supplementation on genomic DNA methylation in patients with colorectal adenoma. Gut. 2005 May;54(5):648-53.
17. Wang S, Low PS: Folate-mediated targeting of antineoplastic drugs, imaging agents, and nucleic acids to cancer cells. J Control Release. 1998 Apr 30;53(1-3):39-48.
18. Hankey GJ, Eikelboom JW, Loh K, Tang M, Pizzi J, Thom J, Yi Q: Sustained homocysteine-lowering effect over time of folic acid-based multivitamin therapy in stroke patients despite increasing folate status in the population. Cerebrovasc Dis. 2005;19(2):110-6. Epub 2004 Dec 17.
19. Ramaekers VT, Rothenberg SP, Sequeira JM, Opladen T, Blau N, Quadros EV, Selhub J: Autoantibodies to folate receptors in the cerebral folate deficiency syndrome. N Engl J Med. 2005 May 12;352(19):1985-91.
20. Verwei M, Arkbage K, Mocking H, Havenaar R, Groten J: The binding of folic acid and 5-methyltetrahydrofolate to folate-binding proteins during gastric passage differs in a dynamic in vitro gastrointestinal model. J Nutr. 2004 Jan;134(1):31-7.
21. Mattson MP: Will caloric restriction and folate protect against AD and PD? Neurology. 2003 Feb 25;60(4):690-5.
22. Omura Y: Excessive use of Steroid Hormone & beneficial effects of True St. 36 acupuncture on malignant brain tumors--part I; how to estimate non-invasively presence of excess dose of Steroid Hormone in patients, baseball players & other professional athletes from its toxic effects on heart & pancreas, as well as persistent or recurrent infection--part II. Acupunct Electrother Res. 2005;30(1-2):57-102.
23. Paulionis L, Kane SL, Meckling KA: Vitamin status and cognitive function in a long-term care population. BMC Geriatr. 2005 Dec 13;5:16.
24. Zhu WY, Alliegro MA, Melera PW: The rate of folate receptor alpha (FR alpha) synthesis in folate depleted CHL cells is regulated by a translational mechanism sensitive to media folate levels, while stable overexpression of its mRNA is mediated by gene amplification and an increase in transcript half-life. J Cell Biochem. 2001 Mar 26;81(2):205-19.
25. Tchantchou F: Homocysteine metabolism and various consequences of folate deficiency. J Alzheimers Dis. 2006 Aug;9(4):421-7.
26. Lu S, Chen GL, Ren C, Kwabi-Addo B, Epner DE: Methionine restriction selectively targets thymidylate synthase in prostate cancer cells. Biochem Pharmacol. 2003 Sep 1;66(5):791-800.
27. Durga J, van Boxtel MP, Schouten EG, Bots ML, Kok FJ, Verhoef P: Folate and the methylenetetrahydrofolate reductase 677C-->T mutation correlate with cognitive performance. Neurobiol Aging. 2006 Feb;27(2):334-43. Epub 2005 Feb 24.
28. Stuerenburg HJ, Ganzer S, Arlt S, Muller-Thomsen T: The influence of smoking on plasma folate and lipoproteins in Alzheimer disease, mild cognitive impairment and depression. Neuro Endocrinol Lett. 2005 Jun;26(3):261-3.
29. Smith DE, Kok RM, Teerlink T, Jakobs C, Smulders YM: Quantitative determination of erythrocyte folate vitamer distribution by liquid chromatography-tandem mass spectrometry. Clin Chem Lab Med. 2006;44(4):450-9.
30. Wolters M, Strohle A, Hahn A: [Age-associated changes in the metabolism of vitamin B(12) and folic acid: prevalence, aetiopathogenesis and pathophysiological consequences]. Z Gerontol Geriatr. 2004 Apr;37(2):109-35.
31. Sahr T, Ravanel S, Rebeille F: Tetrahydrofolate biosynthesis and distribution in higher plants. Biochem Soc Trans. 2005 Aug;33(Pt 4):758-62.