Showing Compound 10-Formyltetrahydrofolic acid (FDB022345)

Record Information

Version

1.0

Creation date

2011-09-21 00:12:31 UTC

Update date

2020-09-17 15:40:32 UTC

Primary ID

FDB022345

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

10-Formyltetrahydrofolic acid

Description

10-Formyltetrahydrofolate, also known as 10-formyl-THF or 10-formyl-H4pteglu1, 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. ightleftharpoons } CH2H2F + NADH + H+In the second step 5,10-methenyltetrahydrofolate undergoes hydrolysis:CH2H2F + H2O ⇌ {\displaystyle. 10-Formyltetrahydrofolate is a strong basic compound (based on its pKa). 10-Formyltetrahydrofolate exists in all eukaryotes, ranging from yeast to humans. Within humans, 10-formyltetrahydrofolate participates in a number of enzymatic reactions. In particular, 10-formyltetrahydrofolate and glycineamideribotide can be converted into tetrahydrofolic acid and 5'-phosphoribosyl-N-formylglycinamide through the action of the enzyme trifunctional purine biosynthetic protein adenosine-3. In addition, 10-formyltetrahydrofolate and AICAR can be converted into tetrahydrofolic acid and phosphoribosyl formamidocarboxamide; which is catalyzed by the enzyme bifunctional purine biosynthesis protein purh. In these reactions 10-CHO-THF is used as a substrate in formyltransferase reactions. In humans, 10-formyltetrahydrofolate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. Outside of the human body, 10-Formyltetrahydrofolate has been detected, but not quantified in, several different foods, such as breadfruits, catjang pea, climbing beans, kai-lans, and pears. This could make 10-formyltetrahydrofolate a potential biomarker for the consumption of these foods. 10-CHO-THF is required for the formylation of methionyl-tRNA formyltransferase to give fMet-tRNA.10-CHO-THF is produced from methylenetetrahydrofolate (CH2H4F) via a two step process. Two equivalents of 10-CHO-THF are required in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase. ightleftharpoons } 10-formyltetrahydrofolate10-CHO-THF is also produced by the reactionATP + formate + tetrahydrofolate ⇌ {\displaystyle. 10-Formyltetrahydrofolate (10-CHO-THF) is a form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. It can be converted back into tetrahydrofolate (THF) by formyltetrahydrofolate dehydrogenase or THF and formate by formyltetrahydrofolate deformylase. ightleftharpoons } ADP + phosphate + 10-formyltetrahydrofolateThis reaction is catalyzed by formate-tetrahydrofolate ligase.

CAS Number

2800-34-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
10-Formyl-(6Rs)-tetrahydrofolic acid	HMDB
10-Formyl-(6RS)-tetrahydrofolic acid	hmdb
10-Formyl-H4pteglu1	HMDB
10-Formyl-H4PteGlu1	hmdb
10-Formyl-tetrahydrofolate	HMDB
10-Formyl-THF	Kegg
10-Formyltetrahydrofolate	hmdb
10-Formyltetrahydrofolic acid	Generator
10-Formyltetrahydropteroylglutamate	HMDB
10-Formyltetrahydropteroylglutamic acid	HMDB

Showing 1 to 10 of 23 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	5.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	216.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	135.7 m³·mol⁻¹	ChemAxon
Polarizability	46.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C20H23N7O7

IUPAC name

(2S)-2-[(4-{N-[(4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid

InChI Identifier

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

InChI Key

AUFGTPPARQZWDO-YUZLPWPTSA-N

Isomeric 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

Average Molecular Weight

473.4393

Monoisotopic Molecular Weight

473.165896125

Classification

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

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	10-Formyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004j-2733900000-d416b73a1673d1220b87	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0v4i-2913374000-7b894dbf7f83fe5cd9d7	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	10-Formyltetrahydrofolic acid, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05cr-0401900000-21104c38dc03ca4e7a0e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003r-0935700000-2f12524764eca10dcf15	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0910000000-03f41886e7967d0201eb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-1244cea99701ed75f41c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bc-1123900000-cdcadc51a3f47cb93886	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9842000000-62efadef6701421ce2c5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0002900000-e6e9d4109ecb3ef0bbee	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1729400000-02f5fdbf97e3ce7a3a95	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-0932000000-68bdb6e09b80b22288c6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-19d839ffa3d1b1988450	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0200900000-93ad732aff1ff91aa085	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0v03-4920300000-17e6f1c09b0e093800ef	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

109092

ChEMBL ID

Not Available

KEGG Compound ID

C00234

Pubchem Compound ID

122347

Pubchem Substance ID

Not Available

ChEBI ID

15637

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00972

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34337

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

10-formyl-tetrahydrofolate

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Bifunctional purine biosynthesis protein PURH	ATIC	P31939
C-1-tetrahydrofolate synthase, cytoplasmic	MTHFD1	P11586
Cytosolic 10-formyltetrahydrofolate dehydrogenase	ALDH1L1	O75891
Methionyl-tRNA formyltransferase, mitochondrial	MTFMT	Q96DP5
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	MTHFD2	Q7Z650
Mitochondrial 10-formyltetrahydrofolate dehydrogenase	ALDH1L2	Q3SY69
Monofunctional C1-tetrahydrofolate synthase, mitochondrial	MTHFD1L	Q6UB35
Trifunctional purine biosynthetic protein adenosine-3	GART	P22102