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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-20 20:33:03 UTC
HMDB IDHMDB0001534
Secondary Accession Numbers
  • HMDB01534
Metabolite Identification
Common Name5-Formiminotetrahydrofolic acid
Description5-formiminotetrahydrofolic acid is a member of the class of compounds known as tetrahydrofolic acids. Tetrahydrofolic acids are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 5-formiminotetrahydrofolic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, 5-formiminotetrahydrofolic acid is primarily located in the cytoplasm (predicted from logP). In humans, 5-formiminotetrahydrofolic acid is involved in few metabolic pathways, which include folate malabsorption, hereditary, folate metabolism, histidine metabolism, and methotrexate pathway. 5-formiminotetrahydrofolic acid is also involved in a couple of metabolic disorders, which include histidinemia and methylenetetrahydrofolate reductase deficiency (MTHFRD). 5-formiminotetrahydrofolic acid is an intermediate in the catabolism of histidine. It is produced by glutamate formimidoyltransferase and then converted into 5,10-methenyltetrahydrofolate by formiminotransferase cyclodeaminase (Wikipedia). 5-Formiminotetrahydrofolic acid is a substrate for Formimidoyltransferase-cyclodeaminase..
Structure
Thumb
Synonyms
ValueSource
5-FormimidoyltetrahydrofolateKegg
5-Formimidoyltetrahydrofolic acidGenerator
5-FormiminotetrahydrofolateGenerator
Chemical FormulaC20H24N8O6
Average Molecular Weight472.4546
Monoisotopic Molecular Weight472.18188054
IUPAC Name2-[(4-{[(2-amino-5-carboximidoyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional Name2-[(4-{[(2-amino-5-carboximidoyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
CAS Registry Number2311-81-1
SMILES
NC1=NC2=C(N(C=N)C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)CN2)C(=O)N1
InChI Identifier
InChI=1S/C20H24N8O6/c21-9-28-12(8-24-16-15(28)18(32)27-20(22)26-16)7-23-11-3-1-10(2-4-11)17(31)25-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,21,23H,5-8H2,(H,25,31)(H,29,30)(H,33,34)(H4,22,24,26,27,32)
InChI KeyYCWUVLPMLLBDCU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentTetrahydrofolic acids
Alternative Parents
Substituents
  • Tetrahydrofolic acid
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino 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
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Azacycle
  • Formamidine
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Secondary amine
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Imine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP-1.8ALOGPS
logP-3.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
pKa (Strongest Basic)6.04ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area222.33 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity139.53 m³·mol⁻¹ChemAxon
Polarizability47.06 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1444900000-227217d565370340172fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uk9-3331397000-01cb800442c1e1c96e39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0031900000-bf344326ac22f287aa35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0393500000-8fc7ac6d67efd44cfedcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-1791000000-b39eab982a3930dc5ed6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-d1729aece34f4a1b8ce0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufu-0012900000-ff4f88b4c580913c8482View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9463200000-b3fbdf5da75999d625c5View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Folate malabsorption, hereditaryThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Folate MetabolismThumbThumb?image type=greyscaleThumb?image type=simpleMap00670
Histidine MetabolismThumbThumb?image type=greyscaleThumb?image type=simpleMap00340
HistidinemiaThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Methotrexate Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022676
KNApSAcK IDNot Available
Chemspider ID11267158
KEGG Compound IDC00664
BioCyc ID5-FORMIMINO-THF
BiGG ID35643
Wikipedia LinkNot Available
METLIN ID6305
PubChem Compound530
PDB IDNot Available
ChEBI ID15639
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool. Binds and promotes bundling of vimentin filaments originating from the Golgi (By similarity).
Gene Name:
FTCD
Uniprot ID:
O95954
Molecular weight:
58925.93
Reactions
5-Formiminotetrahydrofolic acid + L-Glutamic acid → Tetrahydrofolic acid + Formiminoglutamic aciddetails
5-Formiminotetrahydrofolic acid → 5,10-Methenyltetrahydrofolic acid + Ammoniadetails
5-Formiminotetrahydrofolic acid + L-Glutamic acid → Tetrahydrofolic acid + Formiminoglutamic aciddetails
5-Formiminotetrahydrofolic acid + Hydrogen Ion → 5,10-Methenyltetrahydrofolic acid + Ammoniadetails