tetrahydrofolate (PAMDB120090)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120090
Identification
Name: tetrahydrofolate
Description:Dianion of (6S)-5,6,7,8-tetrahydrofolic acid arising from deprotonation of both carboxylic acid functions.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (6S)-5,6,7,8-tetrahydrofolate
  • (6S)-5,6,7,8-tetrahydrofolate dianion
Chemical Formula: C19H21N7O6
Average Molecular Weight: 443.418
Monoisotopic Molecular Weight: 445.171
InChI Key: MSTNYGQPCMXVAQ-KIYNQFGBSA-L
InChI:InChI=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)/p-2/t11?,12-/m0/s1
CAS number: 135-16-0
IUPAC Name:N-[4-({[(6S)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamate
Traditional IUPAC Name: 2-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
SMILES:C(NC1(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=1))C3(CNC2(=C(C(=O)NC(N)=N2)N3))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct Parent Tetrahydrofolic acids
Alternative Parents
Substituents
  • Tetrahydrofolic acid
  • Glutamic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Alpha-amino acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Monocyclic benzene moiety
  • Pyrimidine
  • Primary aromatic amine
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: 250 °C
Experimental Properties:
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.269 g/LNot Available
LogP-2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.27 mg/mLALOGPS
logP-0.96ALOGPS
logP-2.8ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area207.27 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity121.39 m3·mol-1ChemAxon
Polarizability43.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
tetrahydrofolate + trimethyl sulfonium → Hydrogen ion + dimethyl sulfide + N5-methyl-tetrahydropteroyl mono-L-glutamate
N5-hydroxy-L-ornithine + 10-formyl-tetrahydrofolate → N5-formyl-N5-hydroxy-L-ornithine + tetrahydrofolate
Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + 10-formyl-tetrahydrofolate → Hydrogen ion + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + tetrahydrofolate
vanillate + tetrahydrofolate → protocatechuate + N5-methyl-tetrahydropteroyl mono-L-glutamate
10-formyl-tetrahydrofolate + N1-(5-phospho-β-D-ribosyl)glycinamide → Hydrogen ion + tetrahydrofolate + N2-formyl-N1-(5-phospho-β-D-ribosyl)glycinamide
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
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  • 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. [15990733 ]
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  • 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. [15592264 ]
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  • 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. [14711112 ]
  • Pljesa S: [Possible complications of erythropoietin therapy in patients with chronic renal failure] Med Pregl. 2004 May-Jun;57(5-6):254-7. [15503795 ]
  • 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. [9741912 ]
  • 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. [15608435 ]
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  • 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. [14704289 ]
  • Mattson MP: Will caloric restriction and folate protect against AD and PD? Neurology. 2003 Feb 25;60(4):690-5. [12601113 ]
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  • Paulionis L, Kane SL, Meckling KA: Vitamin status and cognitive function in a long-term care population. BMC Geriatr. 2005 Dec 13;5:16. [16351716 ]
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  • 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. [16399216 ]
  • 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. [16599840 ]
  • 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. [15103481 ]
  • Sahr T, Ravanel S, Rebeille F: Tetrahydrofolate biosynthesis and distribution in higher plants. Biochem Soc Trans. 2005 Aug;33(Pt 4):758-62. [16042593 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
METABOLIGHTSMTBLC57453
HMDBHMDB01846
CHEBI57453
BIGG33856
PUBCHEM25790919
CAS135-16-0
LIGAND-CPDC00101
CAS29347-89-5