Showing Compound 5,10-Methylenetetrahydrofolic acid (FDB022675)

Record Information

Version

1.0

Creation date

2011-09-21 00:17:46 UTC

Update date

2020-09-17 15:40:31 UTC

Primary ID

FDB022675

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5,10-Methylenetetrahydrofolic acid

Description

5,10-Methylene-THF, also known as CH2H4folate, 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. It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). 5,10-Methylene-THF is a strong basic compound (based on its pKa). 5,10-Methylene-THF is a substrate for Methylenetetrahydrofolate reductase. 5,10-Methylene-THF exists in all eukaryotes, ranging from yeast to humans. Within humans, 5,10-methylene-THF participates in a number of enzymatic reactions. In particular, dihydrolipoate and 5,10-methylene-THF can be biosynthesized from tetrahydrofolic acid and 8-[(aminomethyl)sulfanyl]-6-sulfanyloctanoic acid; which is catalyzed by the enzyme aminomethyltransferase, mitochondrial. In addition, 5,10-methylene-THF and glycine can be converted into tetrahydrofolic acid and L-serine; which is mediated by the enzyme serine hydroxymethyltransferase, mitochondrial. This enzyme converts 5,10-Methylene-THF to 5-methyltetrahydrofolate. 5,10-Methylene-THF is an intermediate in the metabolism of Methane and the metabolism of Nitrogen. In humans, 5,10-methylene-THF is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. This reaction is required for the multistep process that converts the amino acid homocysteine to methionine. The body uses methionine to make proteins and other important compounds. 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. 5,10-Methylene-THF is an intermediate in glycine, serine and threonine metabolism and one carbon metabolism.

CAS Number

31690-11-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
(6R)-5,10-Methylenetetrahydrofolate	Kegg
(6R)-5,10-Methylenetetrahydrofolic acid	Generator
5,10-Methenyltetrahydropteroylglutamate	HMDB
5,10-Methylene-5,6,7,8-tetrahydrofolate	HMDB
5,10-Methylene-6-hydrofolate	HMDB
5,10-Methylene-6-hydrofolic acid	HMDB
5,10-Methylene-THF	hmdb
5,10-Methylenetetrahydrofolate	HMDB
5,10-Methylenetetrahydrofolate monohydrochloride, (L-glu)-isomer	HMDB
5,10-Methylenetetrahydrofolate, (D-glu)-isomer	HMDB

Showing 1 to 10 of 16 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	-0.94	ALOGPS
logP	-2.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	5.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	190.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.77 m³·mol⁻¹	ChemAxon
Polarizability	46.12 Å³	ChemAxon
Number of Rings	4	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

C20H23N7O6

IUPAC name

2-({4-[(6aR)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

InChI Identifier

InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1

InChI Key

QYNUQALWYRSVHF-PZORYLMUSA-N

Isomeric SMILES

[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O

Average Molecular Weight

457.4399

Monoisotopic Molecular Weight

457.170981503

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Biofluid and excreta:

Blood

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

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	5,10-Methylenetetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-1635900000-4b2ed6618451a7e931b1	Spectrum
Predicted GC-MS	5,10-Methylenetetrahydrofolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-2129050000-80e96fb3203322200945	Spectrum
Predicted GC-MS	5,10-Methylenetetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5,10-Methylenetetrahydrofolic acid, non-derivatized, 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	splash10-08fu-0003900000-ce1f75a98c0216d169e2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0229400000-c8c29bf14ef80a73f864	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02u3-1192000000-ab556f50884c7b4fdcbe	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0001900000-6ba3ddeb1f652fdc6b6b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-1225900000-82b75909f87dfeb54211	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9553000000-5aca24c246430955de51	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-0006900000-dd6e195db40930799024	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0109200000-aa6336e6c1c41c98d390	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-1695000000-8b9546bbad524392a35b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-0009800000-1ef964ba403eb61f6bf0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01w3-1407900000-f4b4d0db119b458049fb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-5935200000-5fa8390660d5a558ac8b	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

388320

ChEMBL ID

Not Available

KEGG Compound ID

C00143

Pubchem Compound ID

439175

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01533

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34022

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

5,10-methylenetetrahydrofolate

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Show entries

Search:

Name	Gene Name	UniProt ID
Aminomethyltransferase, mitochondrial	AMT	P48728
C-1-tetrahydrofolate synthase, cytoplasmic	MTHFD1	P11586
Glycine cleavage system H protein, mitochondrial	GCSH	P23434
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	MTHFD2	Q7Z650
Monofunctional C1-tetrahydrofolate synthase, mitochondrial	MTHFD1L	Q6UB35
Serine hydroxymethyltransferase, cytosolic	SHMT1	P34896
Serine hydroxymethyltransferase, mitochondrial	SHMT2	P34897
Thymidylate synthase	TYMS	P04818