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Record Information
Version1.0
Creation Date2016-09-30 22:19:48 UTC
Update Date2020-06-04 20:44:09 UTC
MCDB ID BMDB0000121
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
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
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.174 uM
  • Int. Dairy Journa...
details
Detected and Quantified0.113 uM
  • NRC. 1989. Recomm...
details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.136 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.136 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.261 uM details
Detected and Quantified0.261 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.136 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.109 uM details
Detected and Quantified0.132 uM details
Detected and Quantified0.109 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.113 uM details
Detected and Quantified0.249 uM details
Detected and Quantified0.249 uM details
Detected and Quantified0.249 uM details
Detected and Quantified0.113 uM
  • Park, Y. W; Juáre...
details
Detected and Quantified0.087 +/- 0.004 uM details
Detected and Quantified0.083 +/- 0.001 uM details
Detected and Quantified0.09 +/- 0.01 uM details
Detected and Quantified0.09 +/- 0.01 uM details
HMDB IDHMDB0000121
DrugBank IDDB00158
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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]