Common NameFolate
DescriptionFolic acid or folate, is a vitamin that belongs to the class of compounds known as pterins. Chemically, folate consists of three distinct chemical moieties linked together. A pterin (2-amino-4-hydroxy-pteridine) linked by a methylene bridge to a p-aminobenzoyl group that in turn is linked through an amide linkage to glutamic acid. It is a member of the vitamin B family and is primarily known as vitamin B9. Folate is required for the body to make DNA and RNA and metabolize amino acids necessary for cell division for the hematopoietic system. As humans cannot make folate, it is required in the diet, making it an essential nutrient (i.e. a vitamin). Folate occurs naturally in many foods including mushrooms, spinach, yeast, green leaves, and grasses (poaceae). Folic acid, being biochemically inactive, is converted to tetrahydrofolic acid and methyltetrahydrofolate by the enzyme known as dihydrofolate reductase. Tetrahydrofolate and methyltetrahydrofolate are transported across cells by receptor-mediated endocytosis where they are needed to maintain normal erythropoiesis, synthesize purine and thymidylate nucleic acids, interconvert amino acids and generate formic acid. Folic acid is used in the treatment and prevention of folate deficiencies and megaloblastic anemia. Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in babies. Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs (PMID: 28097362 ). Folic acid is also a microbial metabolite produced by Bifidobacterium and Lactobacillus (PMID: 22254078 ).
Structure
Molecular FormulaC19H19N7O6
Average Mass441.39750
Monoisotopic Mass441.13968
IUPAC Name(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional NameFolic acid
CAS Registry Number59-30-3
SMILESNc1nc2ncc(CNc3ccc(C(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-])cc3)nc2c(=O)[nH]1
InChI IdentifierInChI=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
CHEBI IDCHEBI:62501
HMDB IDHMDB0000121
Pathways
NameSMPDB/PathBank
One carbon pool by folate
Pterine Biosynthesis
Methotrexate Action Pathway
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Folate malabsorption, hereditary
StateSolid
Water Solubility7.61e-02 g/l
logP-0.04
logS-3.76
pKa (Strongest Acidic)3.37
pKa (Strongest Basic)2.09
Hydrogen Acceptor Count12
Hydrogen Donor Count6
Polar Surface Area208.99 Ų
Rotatable Bond Count9
Physiological Charge-2
Formal Charge0
Refractivity111.01 m³·mol⁻¹
Polarizability42.06

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