ECMDB: N10-Formyl-THF (ECMDB00972) (M2MDB000213)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (7)XML

Proteins (2340)

Record Information

Version

2.0

Creation Date

2012-05-31 13:02:47 -0600

Update Date

2015-09-17 15:41:07 -0600

Secondary Accession Numbers

ECMDB00972

Identification

Name:

N10-Formyl-THF

Description

N10-Formyl-THF is a substrate for Trifunctional purine biosynthetic protein adenosine-3, Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, 10-formyltetrahydrofolate dehydrogenase, Folylpolyglutamate synthase, Bifunctional purine biosynthesis protein PURH and C-1-tetrahydrofolate synthase (cytoplasmic).

Structure

MOL SDF PDB SMILES InChI

Synonyms:

10-Formyl-(6RS)-tetrahydrofolate
10-Formyl-(6RS)-tetrahydrofolic acid
10-Formyl-H4PteGlu1
10-formyl-H₄PteGlu₁
10-Formyl-tetrahydrofolate
10-Formyl-tetrahydrofolic acid
10-Formyl-THF
10-Formyltetrahydrofolate
10-Formyltetrahydrofolic acid
10-Formyltetrahydropteroylglutamate
10-Formyltetrahydropteroylglutamic acid
10-Fthf
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-Glutamate
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-Glutamic acid
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-Glutamate
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-Glutamic acid
N10-Formyl-5,6,7,8-tetrahydrofolate
N10-Formyl-5,6,7,8-tetrahydrofolic acid
N10-formyl-H4F
N10-formyl-tetrahydrofolate
N10-formyl-tetrahydrofolic acid
N10-formyl-THF
N10-Formyltetrahydrofolate
N10-Formyltetrahydrofolic acid
N10-Formyltetrahydropteroylglutamate
N10-Formyltetrahydropteroylglutamic acid
N¹⁰-formyl-H₄F
N¹⁰-formyl-tetrahydrofolate
N¹⁰-formyl-THF

Chemical Formula:

C₂₀H₂₃N₇O₇

Weight:

Average: 473.4393
Monoisotopic: 473.165896125

InChI Key:

AUFGTPPARQZWDO-YUZLPWPTSA-N

InChI:

InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1

CAS number:

2800-34-2

IUPAC Name:

(2S)-2-{[4-(N-{[(6R)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid

Traditional IUPAC Name:

10-formyltetrahydrofolic acid

SMILES:

NC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1

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
Acylaminobenzoic acid or derivatives
Alpha-amino acid or derivatives
Anilide
Benzoic acid or derivatives
Benzamide
Benzoyl
Pyrimidone
Aminopyrimidine
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous amide
Tertiary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid
Carboxylic acid derivative
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

formyltetrahydrofolic acid (CHEBI:15637 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-3.4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.82	ChemAxon
pKa (Strongest Basic)	4.47	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	215.55 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	124.88 m³·mol⁻¹	ChemAxon
Polarizability	46.63 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

Reactions:

AICAR + 10-Formyltetrahydrofolate + N10-Formyl-THF > FAICAR + tetrahydropteroyl mono-L-glutamate
L-Methionyl-tRNA + N10-Formyl-THF <> Tetrahydrofolic acid + N-Formylmethionyl-tRNA
N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid
Water + 5 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion
N10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide
N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid
Water + 5 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion

More...

SMPDB Pathways:

One Carbon Pool by Folate I	PW001735
One carbon pool by folate	PW000773
polymyxin resistance	PW002052
purine nucleotides de novo biosynthesis	PW000910
purine nucleotides de novo biosynthesis 2	PW002033

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
Aminoacyl-tRNA biosynthesis ec00970
Glyoxylate and dicarboxylate metabolism ec00630
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
One carbon pool by folate ec00670
Purine metabolism ec00230

EcoCyc Pathways:

5-aminoimidazole ribonucleotide biosynthesis I PWY-6121
folate polyglutamylation PWY-2161
formylTHF biosynthesis I 1CMET2-PWY
inosine-5'-phosphate biosynthesis I PWY-6123
polymyxin resistance PWY0-1338
tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate PWY-6613

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_35) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a7i-0301900000-731bc9348489f24f80ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003r-0936800000-ade646bc1baf4b8851af	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-0910000000-a7975e3a08f3a92a4ce2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-53fa6981f67bce467289	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uml-1122900000-95a426dd0ca2a0207dbb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9741000000-dbaf84d2dcb0c0d71757	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Denis V; Daignan-Fornier B Synthesis of glutamine, glycine and 10-formyl tetrahydrofolate is coregulated with purine biosynthesis in Saccharomyces cerevisiae. Molecular & general genetics : MGG (1998), 259(3), 246-55.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15637
HMDB ID	HMDB00972
Pubchem Compound ID	10
Kegg ID	C00234
ChemSpider ID	109092
Wikipedia	10-formyl-tetrahydrofolate
BioCyc ID	10-FORMYL-THF
EcoCyc ID	10-FORMYL-THF

Enzymes

Protein Details

1. Phosphoribosylglycinamide formyltransferase

General function:: Involved in hydroxymethyl-, formyl- and related transferase activity
Specific function:: 10-formyltetrahydrofolate + N(1)-(5-phospho-D- ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5- phospho-D-ribosyl)glycinamide
Gene Name:: purN
Uniprot ID:: P08179
Molecular weight:: 23238

Reactions

10-formyltetrahydrofolate + N(1)-(5-phospho-D-ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide.

Protein Details

2. Bifunctional purine biosynthesis protein purH

General function:: Involved in IMP cyclohydrolase activity
Specific function:: 10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Gene Name:: purH
Uniprot ID:: P15639
Molecular weight:: 57329

Reactions

10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
IMP + H(2)O = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.

Protein Details

3. Methionyl-tRNA formyltransferase

General function:: Involved in methionyl-tRNA formyltransferase activity
Specific function:: Modifies the free amino group of the aminoacyl moiety of methionyl-tRNA(fMet). The formyl group appears to play a dual role in the initiator identity of N-formylmethionyl-tRNA by:(I) promoting its recognition by IF2 and (II) impairing its binding to EFTu-GTP
Gene Name:: fmt
Uniprot ID:: P23882
Molecular weight:: 34168

Reactions

10-formyltetrahydrofolate + L-methionyl-tRNA(fMet) + H(2)O = tetrahydrofolate + N-formylmethionyl-tRNA(fMet).

Protein Details

4. Bifunctional protein folD

General function:: Involved in nucleotide binding
Specific function:: Catalyzes the oxidation of 5,10- methylenetetrahydrofolate to 5,10-methenyltetrahydrofolate and then the hydrolysis of 5,10-methenyltetrahydrofolate to 10- formyltetrahydrofolate. This enzyme is specific for NADP
Gene Name:: folD
Uniprot ID:: P24186
Molecular weight:: 31044

Reactions

5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O = 10-formyltetrahydrofolate.

Protein Details

5. Phosphoribosylglycinamide formyltransferase 2

General function:: Involved in ATP binding
Specific function:: Catalyzes two reactions:the first one is the production of beta-formyl glycinamide ribonucleotide (GAR) from formate, ATP and beta GAR; the second, a side reaction, is the production of acetyl phosphate and ADP from acetate and ATP
Gene Name:: purT
Uniprot ID:: P33221
Molecular weight:: 42433

Reactions

Formate + ATP + 5'-phospho-ribosylglycinamide = 5'-phosphoribosyl-N-formylglycinamide + ADP + diphosphate.

Protein Details

6. Formyltetrahydrofolate deformylase

General function:: Involved in amino acid binding
Specific function:: Produces formate from formyl-tetrahydrofolate. Provides the major source of formate for the purT-dependent synthesis of 5'-phosphoribosyl-N-formylglycinamide (FGAR) during aerobic growth. Has a role in regulating the one-carbon pool
Gene Name:: purU
Uniprot ID:: P37051
Molecular weight:: 31934

Reactions

10-formyltetrahydrofolate + H(2)O = formate + tetrahydrofolate.

Protein Details

7. Bifunctional polymyxin resistance protein ArnA

General function:: Involved in hydroxymethyl-, formyl- and related transferase activity
Specific function:: Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto- arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4- amino-4-deoxy-L-arabinose (UDP-L-Ara4N) to form UDP-L-4-formamido- arabinose (UDP-L-Ara4FN). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:: arnA
Uniprot ID:: P77398
Molecular weight:: 74288

Reactions

UDP-alpha-D-glucuronate + NAD(+) = UDP-beta-L-threo-pentapyranos-4-ulose + CO(2) + NADH.
10-formyltetrahydrofolate + UDP-4-amino-4-deoxy-beta-L-arabinose = 5,6,7,8-tetrahydrofolate + UDP-4-deoxy-4-formamido-beta-L-arabinose.

N10-Formyl-THF (ECMDB00972) (M2MDB000213)

Structure for #<Compound:0xa73df494>

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