5-Formyltetrahydrofolic acid (YMDB00516)

Identification

YMDB ID

YMDB00516

Name

5-Formyltetrahydrofolic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

5-Formyltetrahydrofolate (N5-Formyl-THF) is a folate coenzyme. Tetrahydrofolate (vitamin B9) and its derivatives, commonly termed folates, are essential cofactors that facilitate the transfer of one-carbon units from donor molecules into important biosynthetic pathways leading to methionine, purine, and pyrimidine biosynthesis. Folates also mediate the interconversion of serine and glycine, and play a role in histidine catabolism. Although 5-Formyl-tetrahydrofolate is the most stable derivative of the reduced folates, it is the only folate derivative that does not serve as a cofactor in C1-metabolism. [Biocyc PWY-2201] [PMID: 11923304]

Structure

MOL SDF PDB SMILES InChI

Synonyms

(6R,S)-5-Formyltetrahydrofolate
(6S)-5-formyltetrahydrofolate
(6S)-5-HCO-H4folate
[(6S)-5-formyl-5,6,7,8-tetrahydropteroyl]glutamate
10-Formyl-7,8-dihydrofolate
10-Formyl-7,8-dihydrofolic acid
5-Formyl-5,6,7,8-tetrahydrofolate
5-Formyl-5,6,7,8-tetrahydrofolic acid
5-Formyltetrahydrofolate
5-formyltetrahydrofolic acid
5-Formyltetrahydropteroylglutamate
5-Formyltetrahydropteroylglutamic acid
folinate
folinic acid
Folinic acid-SF
l-Leucovorin
l(-)-5-formyl-5,6,7,8-tetrahydrofolic acid
Leucal
Leucovorin
Levoleucovorin
N-(5-formyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid
N5-Formyl-5,6,7,8-tetrahydrofolate
N5-Formyl-5,6,7,8-tetrahydrofolic acid
N5-Formyltetrahydrofolate
N5-Formyltetrahydrofolic acid
Welcovorin
(6S)-5-Formyl-5,6,7,8-tetrahydrofolic acid
(6S)-Folinic acid
(6S)-Leucovorin
(S)-Leucovorin
Citrovorum factor
L-Folinic acid
Levofolene
Levofolinic acid
N-[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
(6S)-5-Formyl-5,6,7,8-tetrahydrofolate
(6S)-Folinate
L-Folinate
Levofolinate
N-[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamate
Pteroyl-D-glutamate
5 Formyltetrahydropteroylglutamate
Calcium folinate
Leucovorin, (S)-isomer
Leucovorin, monosodium salt
Leucovorin, (R)-isomer
Leucovorin, calcium
Leucovorin, calcium (1:1) salt, (DL)-isomer
Leucovorin, calcium (1:1) salt, (S)-isomer
Leukovorin
Leukovorum
Monosodium salt leucovorin
Wellcovorin
Levo leucovorin
6 S Leucovorin
Acid, folinic
Factor, citrovorum
Folinic acid SF
Fusilev
Leucovorin, calcium (1:1) salt, pentahydrate
Leucovorin, monopotassium salt, (S)-isomer
N(5)-Formyltetrahydrofolate
S-Leucovorin
5 Formyltetrahydrofolate
6-S-Leucovorin
6S Leucovorin
6S-Leucovorin
Calcium leucovorin
Folinate, calcium
Leucovorin, (D)-isomer
Leucovorin, (DL)-isomer
Leucovorin, calcium (1:1) salt
Leucovorin, monosodium salt, (S)-isomer
S Leucovorin
Levo-leucovorin
5-Formyl-(6S)-tetrahydrofolic acid
CF
Kunyrin
Leucoverin
N5-Formyl-THF
(6S)-5-Formyltetrahydrofolic acid

CAS number

58-05-9

Weight

Average: 473.4393
Monoisotopic: 473.165896125

InChI Key

VVIAGPKUTFNRDU-STQMWFEESA-N

InChI

InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12-,13-/m0/s1

IUPAC Name

(2S)-2-{[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

Traditional IUPAC Name

(2S)-2-{[4-({[(6S)-2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

Chemical Formula

C₂₀H₂₃N₇O₇

SMILES

[H]C(=O)N1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins 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
Aniline or substituted anilines
Phenylalkylamine
Aminopyrimidine
Secondary aliphatic/aromatic amine
Pyrimidone
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous amide
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary amine
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

5-formyltetrahydrofolic acid (CHEBI:63606 )

Physical Properties

State

Solid

Charge

Melting point

245 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-2.7	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	2.81	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	215.55 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.46 m³·mol⁻¹	ChemAxon
Polarizability	46.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm, Mitochondrion

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

One carbon pool by folate

ec00670

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0adi-0031900000-15cbae867ecd4a003ef0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-0393400000-73f11f6c59198eafb45f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-0591000000-ea5c6303d77ffa4af0cb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-a3ae54a4d9b2cae45b72	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bc-1243900000-4ea7b3b1902e6a1204e5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-7973000000-df3edd5bd8661611dd06	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-0005900000-5985bdc6c069ecc00046	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056s-1597400000-db859aadd61942f2e80b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o0-0921000000-ddf359b6fc3776d45401	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-56bf354a786254d088f4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-1220900000-d93259006e38248d26b4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-5920100000-575460bfef119781af80	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	15640
HMDB ID	HMDB01562
Pubchem Compound ID	54575
Kegg ID	C03479
ChemSpider ID	131714
FOODB ID	FDB112383
Wikipedia	Folinate
BioCyc ID	5-FORMYL-THF

Enzymes

Protein Details

1. 5-formyltetrahydrofolate cyclo-ligase

General function:: Involved in ATP binding
Specific function:: Utilizes 5-formyltetrahydrofolate (folinic acid) as substrate in an alternative way of folate biosynthesis
Gene Name:: FAU1
Uniprot ID:: P40099
Molecular weight:: 24058.5

Reactions

ATP + 5-formyltetrahydrofolate → ADP + phosphate + 5,10-methenyltetrahydrofolate.

Protein Details

2. Pyruvate dehydrogenase E1 component subunit alpha, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2)
Gene Name:: PDA1
Uniprot ID:: P16387
Molecular weight:: 46342.69922

Reactions

Pyruvate + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine → [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + CO(2).

Structure for #<Compound:0xaf9b3958>

Enzymes

Reactions

Reactions