P. aeruginosa Metabolome Database: N10-Formyl-THF (PAMDB000213)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000213

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 View Structure

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

Average Molecular Weight:

473.4393

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound belongs to the class of organic compounds known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzamides

Direct Parent

Hippuric acids

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Pterin
Pteridine
Aminobenzoic acid or derivatives
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Benzoic acid or derivatives
Aminobenzamide
Benzoyl
Hydroxypyrimidine
Secondary aliphatic/aromatic amine
Amino fatty acid
Fatty acyl
Pyrimidine
Dicarboxylic acid or derivatives
Heteroaromatic compound
Tertiary carboxylic acid amide
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Secondary amine
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	0.349 mg/mL	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:

Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > 10-Formyltetrahydrofolate + Glycineamideribotide + N10-Formyl-THF + Glycineamideribotide
Formic acid + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + 10-Formyltetrahydrofolate + N10-Formyl-THF
Tetrahydrofolic acid + N-formylmethionyl-tRNA(fMet) + Tetrahydrofolic acid L-methionyl-tRNA(Met) + 10-Formyltetrahydrofolate + N10-Formyl-THF
Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + an N10-formyl-tetrahydrofolate + N10-Formyl-THF > UDP-4-Deoxy-4-formamido-beta-L-arabinose + Hydrogen ion + a tetrahydrofolate + Tetrahydrofolic acid
AICAR + 10-Formyltetrahydrofolate + N10-Formyl-THF > FAICAR + tetrahydropteroyl mono-L-glutamate

More...

Pathways:

Amino sugar and nucleotide sugar metabolism pae00520
Aminoacyl-tRNA biosynthesis pae00970
Glyoxylate and dicarboxylate metabolism pae00630
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
One carbon pool by folate pae00670
Purine metabolism pae00230

Spectra

Spectra:

Spectrum Type	Description	Splash Key
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

N10-Formyl-THF (PAMDB000213)

Structure for N10-Formyl-THF (PAMDB000213)