Bovine Metabolome Database: Showing metabocard for Folic acid (BMDB0000121)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:48 UTC

Update Date

2020-06-04 20:44:09 UTC

BMDB ID

BMDB0000121

Secondary Accession Numbers

BMDB00121

Metabolite Identification

Common Name

Folic acid

Description

Folic acid, also known as folate or vitamin m, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives 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. Folic acid is a drug which is used for treatment of folic acid deficiency, megaloblastic anemia and in anemias of nutritional supplements, pregnancy, infancy, or childhood. Folic acid exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Folic acid exists in all living species, ranging from bacteria to humans. Folic acid participates in a number of enzymatic reactions, within cattle. In particular, Folic acid can be biosynthesized from dihydrofolic acid through its interaction with the enzyme dihydrofolate reductase. In addition, Folic acid can be converted into folic acid; which is catalyzed by the enzyme proton-coupled folate transporter. In cattle, folic acid is involved in the metabolic pathway called the folate metabolism pathway. Folic acid is a potentially toxic compound. Folic acid has been found to be associated with several diseases known as dimethylglycine dehydrogenase deficiency, bladder infections, fibromyalgia, and hereditary folate malabsorption; also folic acid has been linked to the inborn metabolic disorders including folate deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Folate	ChEBI
Folsaeure	ChEBI
N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid	ChEBI
N-Pteroyl-L-glutamic acid	ChEBI
PGA	ChEBI
PteGlu	ChEBI
Pteroyl-L-glutamic acid	ChEBI
Pteroyl-L-monoglutamic acid	ChEBI
Pteroylglutamic acid	ChEBI
Vitamin BC	ChEBI
Vitamin m	ChEBI
Folicet	Kegg
N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamate	Generator
N-Pteroyl-L-glutamate	Generator
Pteroyl-L-glutamate	Generator
Pteroyl-L-monoglutamate	Generator
Pteroylglutamate	Generator
Acifolic	HMDB
Cytofol	HMDB
Dosfolat b activ	HMDB
Folacid	HMDB
Folacin	HMDB
Folbal	HMDB
Folcidin	HMDB
Foldine	HMDB
Folettes	HMDB
Foliamin	HMDB
Folipac	HMDB
Folsan	HMDB
Folsaure	HMDB
Folsav	HMDB
Folvite	HMDB
Incafolic	HMDB
Liver lactobacillus casei factor	HMDB
Millafol	HMDB
N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid	HMDB
N-[4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid	HMDB
Pteroylmonoglutamic acid	HMDB
Vitamin be	HMDB
Folic acid, (DL)-isomer	HMDB
Folic acid, sodium salt	HMDB
Folic acid, (D)-isomer	HMDB
Folic acid, monosodium salt	HMDB
Folic acid, potassium salt	HMDB
b9, Vitamin	HMDB
Folic acid, calcium salt (1:1)	HMDB
Folic acid, monopotassium salt	HMDB
Vitamin b9	HMDB

Chemical Formula

C₁₉H₁₉N₇O₆

Average Molecular Weight

441.3975

Monoisotopic Molecular Weight

441.139681375

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

59-30-3

SMILES

Not Available

InChI Identifier

InChI=1S/C19H19N7O6/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/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1

InChI Key

OVBPIULPVIDEAO-LBPRGKRZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:545959 )
phenols (CHEBI:545959 )
monomethoxybenzene (CHEBI:545959 )

Ontology

Status

Detected and Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Extracellular

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0016 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Brain
Erythrocyte
Kidney
Liver
Milk

Pathways

Name	SMPDB/Pathwhiz	KEGG
Folate Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Erythrocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	NRC. 1989. Recomm...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.136 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.136 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.261 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.261 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.174 uM	Not Specified	Not Specified	Normal	Int. Dairy Journa...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.136 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.109 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.132 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.109 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.113 uM	Not Specified	Not Specified	Normal	USDA Food Co...	details
Milk	Detected and Quantified	0.249 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.249 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.249 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	0.087 +/- 0.004 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.083 +/- 0.001 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.09 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.09 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000121

DrugBank ID

DB00158

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

27470

References

Synthesis Reference

Piper, James R.; McCaleb, George S.; Montgomery, John A. Synthesis of 10-propargylfolic acid from 2-amino-6-(bromomethyl)-4(1H)-pteridinone. Journal of Heterocyclic Chemistry (1987), 24(1), 279-82.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ingela Andersson, R. Öste (1994). Int. Dairy Journal 4 (1994) 161-172. International Dairy Journal.
NA (1989). NRC. 1989. Recommended Dietary Allowances. 10th ed. Natl. Acad. Press, Washington, DC.. The National Academies Press.
Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
USDA Food Composition Databases [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

Enzyme Details

1. Dihydrofolate reductase

General function:: Coenzyme transport and metabolism
Specific function:: Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFR2 (By similarity).
Gene Name:: DHFR
Uniprot ID:: P00376
Molecular weight:: 21604.0

Reactions

Dihydrofolic acid + NADP → Folic acid + NADPH	details

Enzyme Details

2. Solute carrier family 19 (Folate transporter), member 1

General function:: Involved in folic acid binding
Specific function:: Not Available
Gene Name:: SLC19A1
Uniprot ID:: Q17QC9
Molecular weight:: 56622.0

Enzyme Details

3. SLC19A3 protein

General function:: Involved in folic acid binding
Specific function:: Not Available
Gene Name:: SLC19A3
Uniprot ID:: A7E352
Molecular weight:: 54249.0

Enzyme Details

4. Solute carrier family 19 member 1

General function:: Involved in folic acid binding
Specific function:: Not Available
Gene Name:: SLC19A1
Uniprot ID:: Q0V8L3
Molecular weight:: 34009.0

Enzyme Details

5. Folate receptor 2 (Fetal)

General function:: Involved in receptor activity
Specific function:: Not Available
Gene Name:: FOLR2
Uniprot ID:: Q0VCN9
Molecular weight:: 29333.0

Enzyme Details

6. Folate receptor alpha

General function:: Involved in folic acid binding
Specific function:: Binds to folate and reduced folic acid derivatives and mediates delivery of 5-methyltetrahydrofolate and folate analogs into the interior of cells. Has high affinity for folate and folic acid analogs at neutral pH. Exposure to slightly acidic pH after receptor endocytosis triggers a conformation change that strongly reduces its affinity for folates and mediates their release. Required for normal embryonic development and normal cell proliferation (By similarity).
Gene Name:: FOLR1
Uniprot ID:: P02702
Molecular weight:: 27922.0

Showing metabocard for Folic acid (BMDB0000121)

Structure for BMDB0000121 (Folic acid)

Enzymes

Reactions