Common NameFormate
DescriptionFormic acid is the simplest carboxylic acid. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a byproduct in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer. Urinary formate is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465 ).
Structure
Molecular FormulaCH2O2
Average Mass46.02540
Monoisotopic Mass46.00548
IUPAC Nameformic acid
Traditional NameFormic acid
CAS Registry Number64-18-6
SMILESO=C[O-]
InChI IdentifierInChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
InChI KeyBDAGIHXWWSANSR-UHFFFAOYSA-N
CHEBI IDCHEBI:15740
HMDB IDHMDB0000142
Pathways
NameSMPDB/PathBank
One carbon pool by folate
Tryptophan metabolism
Pterine Biosynthesis
Steroid Biosynthesis
Androgen and Estrogen Metabolism
Ibandronate Action Pathway
Simvastatin Action Pathway
Pravastatin Action Pathway
Rosuvastatin Action Pathway
Alendronate Action Pathway
Lovastatin Action Pathway
Zoledronate Action Pathway
Cerivastatin Action Pathway
Risedronate Action Pathway
Pamidronate Action Pathway
Fluvastatin Action Pathway
Atorvastatin Action Pathway
Hypercholesterolemia
Lysosomal Acid Lipase Deficiency (Wolman Disease)
17-Beta Hydroxysteroid Dehydrogenase III Deficiency
Desmosterolosis
CHILD Syndrome
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
Smith-Lemli-Opitz Syndrome (SLOS)
Methotrexate Action Pathway
Dopa-responsive dystonia
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiency
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)
Hyperphenylalaninemia due to dhpr-deficiency
Segawa syndrome
Sepiapterin reductase deficiency
Cholesteryl ester storage disease
Hyper-IgD syndrome
Mevalonic aciduria
Wolman disease
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Aromatase deficiency
Folate malabsorption, hereditary
Androstenedione Metabolism
StateNot Available
Water Solubility4.77e+02 g/l
logP-0.47
logS1.02
pKa (Strongest Acidic)4.27
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area37.3 Ų
Rotatable Bond Count0
Physiological Charge-1
Formal Charge0
Refractivity8.15 m³·mol⁻¹
Polarizability3.37

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