Showing Compound 5-Formyltetrahydrofolic acid (FDB022689)

Record Information

Version

1.0

Creation date

2011-09-21 00:17:59 UTC

Update date

2015-07-21 06:57:19 UTC

Primary ID

FDB022689

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5-Formyltetrahydrofolic acid

Description

N5-Formyl-THF, also known as leucovorin or rescuvolin, 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. N5-Formyl-THF exists in all living species, ranging from bacteria to plants to humans. N5-Formyl-THF is found, on average, in the highest concentration within lettuces (Lactuca sativa). This could make N5-formyl-THF a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N5-Formyl-THF.

CAS Number

58-05-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
(6R,S)-5-Formyltetrahydrofolate	HMDB
10-Formyl-7,8-dihydrofolate	HMDB
10-Formyl-7,8-dihydrofolic acid	HMDB
5 Formyltetrahydrofolate	MeSH, HMDB
5 Formyltetrahydropteroylglutamate	MeSH, HMDB
5-Formlyl-5,6,7,8-tetrahydrofolate,calcium salt	Generator
5-Formyl-5,6,7,8-tetrahydrofolate	HMDB
5-Formyl-5,6,7,8-tetrahydrofolic acid	HMDB
5-Formyltetrahydrofolate	Kegg
5-Formyltetrahydrofolic acid	Generator

Showing 1 to 10 of 51 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.3	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	2.81	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	126.66 m³·mol⁻¹	ChemAxon
Polarizability	46.54 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

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

InChI Identifier

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

InChI Key

VVIAGPKUTFNRDU-UHFFFAOYSA-N

Isomeric SMILES

NC1=NC2=C(N(C=O)C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)CN2)C(=O)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
Alpha-amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Aniline or substituted anilines
Phenylalkylamine
Aminopyrimidine
Secondary aliphatic/aromatic amine
Pyrimidone
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous amide
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary amine
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location:

Subcellular:

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	5-Formyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-2332900000-5c40a0014d3bb486cb20	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-7225198000-aa48aa22224db36842c7	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_17, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_19, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Formyltetrahydrofolic acid, TMS_2_20, 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	splash10-0a4i-0031900000-31498c227b611f3360ea	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-0393400000-f81606ae4f4b27aadbac	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1591000000-825bc8196995ef0bc1e3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-203ae236b032df3233d7	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0umj-1131900000-5174748fd5288f6523fd	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9674000000-192da85bfca095ec870e	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-0018900000-5cbc8e2351f8b3ec2868	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0139300000-a45a2d1a5cd350ef7860	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0012-1956000000-611d4066a036a7ff475f	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0001900000-20cea700a6b8ce876f5e	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-1304900000-85021f1e80280eb64d56	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fba-3517900000-75ddfa6e2a4565261466	2021-10-12	View Spectrum