Record Information
Version1.0
Creation date2011-09-21 00:16:09 UTC
Update date2015-07-21 06:57:16 UTC
Primary IDFDB022573
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5,10-Methenyltetrahydrofolic acid
DescriptionFolate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. Folinic acid is a form of folate that can help 'rescue' or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. Low concentrations of folate, vitamin B12, or vitamin B6 may increase your level of homocysteine, an amino acid normally found in your blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. Methylene tetrahydrofolate (CH2FH4) is formed from tetrahydrofolate by the addition of methylene groups from one of three carbon donors: formaldehyde, serine, or glycine. Methyl tetrahydrofolate(CH3FH4) can be made from methylene tetrahydrofolate by reduction of the methylene group, and formyl tetrahydrofolate (CHOFH4, folinic acid) is made by oxidation of methylene tetrahydrofolate. In the form of a series of tetrahydrofolate compounds, folate derivatives are substrates in a number of single-carbon-transfer reactions, and also are involved in the synthesis of dTMP (2'-deoxythymidine-5'-phosphate) from dUMP (2'-deoxyuridine-5'-phosphate). It helps convert vitamin B12 to one of its coenzyme forms and helps synthesize the DNA required for all rapidly growing cells. [HMDB]
CAS Number7444-29-3
Structure
Thumb
Synonyms
SynonymSource
5,10-methenyl-THFhmdb
5,10-Methenyltetrahydrofolatehmdb
anhydro-leucovorinhmdb
anhydro-leucovorin ahmdb
anhydroleucovorinhmdb
anhydroleucovorin ahmdb
ch-thfhmdb
methenyl-tetrahydrofolatehmdb
methenyl-thfhmdb
methenyltetrahydrofolatehmdb
methenyltetrahydrofolic acidhmdb
n5-n10-ch-thfhmdb
n5-n10-methenyltetrahydrofolatehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.207 mg/mLALOGPS
logP-0.68ALOGPS
logP-4.9ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)1.27ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area192.29 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity145.01 m3·mol-1ChemAxon
Polarizability43.91 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H21N7O6
IUPAC name(6aR)-3-amino-8-(4-{[(1S)-3-carboxy-1-carboxylatopropyl]carbamoyl}phenyl)-1-oxo-1H,4H,5H,6H,6aH,7H,8H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium
InChI IdentifierInChI=1S/C20H21N7O6/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/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1
InChI KeyInChIKey=MEANFMOQMXYMCT-OLZOCXBDSA-N
Isomeric SMILES[H]OC(=O)C([H])([H])C([H])([H])[C@]([H])(N([H])C(=O)C1=C([H])C([H])=C(C([H])=C1[H])N1C([H])=[N+]2C3=C(N([H])C(=NC3=O)N([H])[H])N([H])C([H])([H])[C@]2([H])C1([H])[H])C([O-])=O
Average Molecular Weight455.424
Monoisotopic Molecular Weight455.155331439
Classification
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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct ParentTetrahydrofolic acids
Alternative Parents
Substituents
  • Tetrahydrofolic acid
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • Alpha-amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Aniline or substituted anilines
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Pyrimidone
  • Primary aromatic amine
  • Pyrimidine
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • 2-imidazoline
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Amidine
  • Azacycle
  • Carboxylic acid amidine
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic salt
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic zwitterion
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-9a74d30be444557240b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-87ffec278a0d552070d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9210100000-8e44a81962b4227dbc32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-6e21d81553cf048dcee3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2000900000-e3e2170131566f2c34e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300100000-8e0fa01b9b99e8b1fea8View in MoNA
ChemSpider ID559356
ChEMBL IDNot Available
KEGG Compound IDC00445
Pubchem Compound ID644350
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01354
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34999
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Trifunctional purine biosynthetic protein adenosine-3GARTP22102
Aminomethyltransferase, mitochondrialAMTP48728
Formimidoyltransferase-cyclodeaminaseFTCDO95954
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD1P11586
Monofunctional C1-tetrahydrofolate synthase, mitochondrialMTHFD1LQ6UB35
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolaseMTHFD2Q7Z650
Pathways
NameSMPDB LinkKEGG Link
Folate MetabolismSMP00053 map00670
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference