Showing Compound tetrahydrofolate (FDB031192)

Record Information

Version

1.0

Creation date

2015-05-07 21:17:42 UTC

Update date

2025-11-19 03:03:16 UTC

Primary ID

FDB031192

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

tetrahydrofolate

Description

Tetrahydrofolic acid, also known as (6s)-tetrahydrofolate or (6s)-thfa, belongs to glutamic acid and derivatives class of compounds. Those are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Tetrahydrofolic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Tetrahydrofolic acid can be found in a number of food items such as malabar plum, parsnip, white lupine, and alpine sweetvetch, which makes tetrahydrofolic acid a potential biomarker for the consumption of these food products. Tetrahydrofolic acid may be a unique S.cerevisiae (yeast) metabolite. Tetrahydrofolic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Tetrahydrofolate is transported across cells by receptor-mediated endocytosis where it is needed to maintain normal erythropoiesis, synthesize purine and thymidylate nucleic acids, interconvert amino acids, methylate tRNA, and generate and use formate (DrugBank).

CAS Number

135-16-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(6S)-Tetrahydrofolate	ChEBI
(6S)-Tetrahydrofolic acid	ChEBI
(6S)-THFA	ChEBI
5,6,7,8-Tetrahydrofolate	ChEBI
Tetrahydrofolate	ChEBI
THF	ChEBI
5,6,7,8-Tetrahydrofolic acid	Generator
5,6,7,8-Tetrahydrofolic acid, (D-(-))-isomer	MeSH
5,6,7,8-Tetrahydrofolic acid, (L)-isomer	MeSH
5,6,7,8-Tetrahydrofolic acid, ion (2-)-isomer	MeSH
Tetrahydropteroylglutamate	MeSH
Tetrahydrofolic acid	ChEBI, KEGG

Predicted Properties

Property	Value	Source
Water Solubility	0.27 g/L	ALOGPS
logP	-0.96	ALOGPS
logP	-4.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	3.58	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	207.27 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	121.39 m³·mol⁻¹	ChemAxon
Polarizability	42.95 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

C19H23N7O6

IUPAC name

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

InChI Identifier

InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1

InChI Key

MSTNYGQPCMXVAQ-KIYNQFGBSA-N

Isomeric SMILES

NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1

Average Molecular Weight

445.4292

Monoisotopic Molecular Weight

445.170981503

Classification

Description

Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enals

Alternative Parents

Substituents

Enal
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:61722 )
monounsaturated fatty acid aldehyde (CHEBI:61722 )
an aldehyde (CPD-13228 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	tetrahydrofolate, TMS_3_54, 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	splash10-0032-0431900000-ff1f3948e47561161293	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0952300000-ed9d84bc39d490f6210e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0920000000-0d0efcb6c323340d20b9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0001900000-abb4cec0eb79b0bd2de1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0v4l-2356900000-2fd17d2f587bbd5e882c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9441000000-8c630c7a3633467d6bb3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0080900000-73480c24ce118e5e02f3	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0390100000-9f24528058374fc56c6d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-0962000000-9a988cf519f340f5d7cf	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005c-0002900000-9587282a39f915386f95	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zi3-2807900000-28355749389d1e225f7b	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-3911000000-e7b1ccb0c9f2d7c8269a	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

CHEMBL2021342

KEGG Compound ID

C00101

Pubchem Compound ID

91443

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00007249

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

Tetrahydrofolic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound tetrahydrofolate (FDB031192)

Structure for FDB031192 (tetrahydrofolate)