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Record Information
Version1.0
Creation Date2016-09-30 22:19:48 UTC
Update Date2020-06-04 20:44:09 UTC
BMDB IDBMDB0000121
Secondary Accession Numbers
  • BMDB00121
Metabolite Identification
Common NameFolic acid
DescriptionFolic 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
Thumb
Synonyms
ValueSource
FolateChEBI
FolsaeureChEBI
N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acidChEBI
N-Pteroyl-L-glutamic acidChEBI
PGAChEBI
PteGluChEBI
Pteroyl-L-glutamic acidChEBI
Pteroyl-L-monoglutamic acidChEBI
Pteroylglutamic acidChEBI
Vitamin BCChEBI
Vitamin mChEBI
FolicetKegg
N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamateGenerator
N-Pteroyl-L-glutamateGenerator
Pteroyl-L-glutamateGenerator
Pteroyl-L-monoglutamateGenerator
PteroylglutamateGenerator
AcifolicHMDB
CytofolHMDB
Dosfolat b activHMDB
FolacidHMDB
FolacinHMDB
FolbalHMDB
FolcidinHMDB
FoldineHMDB
FolettesHMDB
FoliaminHMDB
FolipacHMDB
FolsanHMDB
FolsaureHMDB
FolsavHMDB
FolviteHMDB
IncafolicHMDB
Liver lactobacillus casei factorHMDB
MillafolHMDB
N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acidHMDB
N-[4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acidHMDB
Pteroylmonoglutamic acidHMDB
Vitamin beHMDB
Folic acid, (DL)-isomerHMDB
Folic acid, sodium saltHMDB
Folic acid, (D)-isomerHMDB
Folic acid, monosodium saltHMDB
Folic acid, potassium saltHMDB
b9, VitaminHMDB
Folic acid, calcium salt (1:1)HMDB
Folic acid, monopotassium saltHMDB
Vitamin b9HMDB
Chemical FormulaC19H19N7O6
Average Molecular Weight441.3975
Monoisotopic Molecular Weight441.139681375
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number59-30-3
SMILESNot 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 KeyOVBPIULPVIDEAO-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0016 mg/mLNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Brain
  • Erythrocyte
  • Kidney
  • Liver
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
    • NRC. 1989. Recomm...
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot SpecifiedNormal
    • Park, Y. W; Juáre...
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.136 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.136 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.261 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.261 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.174 uMNot SpecifiedNot Specified
Normal
    • Int. Dairy Journa...
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.136 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.109 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.132 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.109 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.113 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.249 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.249 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.249 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.087 +/- 0.004 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.083 +/- 0.001 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.09 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.09 +/- 0.01 uMNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000121
DrugBank IDDB00158
Phenol Explorer Compound IDNot Available
FooDB IDFDB014504
KNApSAcK IDC00001539
Chemspider ID5815
KEGG Compound IDC00504
BioCyc IDCPD-12826
BiGG ID35180
Wikipedia LinkFolic_Acid
METLIN ID246
PubChem Compound6037
PDB IDNot Available
ChEBI ID27470
References
Synthesis ReferencePiper, 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
  1. Ingela Andersson, R. Öste (1994). Int. Dairy Journal 4 (1994) 161-172. International Dairy Journal.
  2. NA (1989). NRC. 1989. Recommended Dietary Allowances. 10th ed. Natl. Acad. Press, Washington, DC.. The National Academies Press.
  3. 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.
  4. 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.
  5. USDA Food Composition Databases [Link]
  6. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

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 + NADPHdetails
General function:
Involved in folic acid binding
Specific function:
Not Available
Gene Name:
SLC19A1
Uniprot ID:
Q17QC9
Molecular weight:
56622.0
General function:
Involved in folic acid binding
Specific function:
Not Available
Gene Name:
SLC19A3
Uniprot ID:
A7E352
Molecular weight:
54249.0
General function:
Involved in folic acid binding
Specific function:
Not Available
Gene Name:
SLC19A1
Uniprot ID:
Q0V8L3
Molecular weight:
34009.0
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
FOLR2
Uniprot ID:
Q0VCN9
Molecular weight:
29333.0
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