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Identification
YMDB IDYMDB00385
NameFormic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFormic acid (methanoic acid) is the simplest carboxylic acid. It is an intermediate in normal metabolism and occurs naturally, most notably in the venom of bee and ant stings. Esters, salts, and the anion derived from formic acid are referred to as formates.
Structure
Thumb
Synonyms
  • Add-F
  • Amasil
  • Ameisensaeure
  • Ameisensaure
  • Aminate
  • Aminic acid
  • Bilorin
  • Collo-Bueglatt
  • Collo-Didax
  • FMT
  • Formate
  • formic acid
  • Formira
  • Formisoton
  • Formylate
  • Formylic acid
  • HCO2 anion
  • HCOOH
  • Hydrogen carboxylate
  • Hydrogen carboxylic acid
  • hydrogencarboxylic acid
  • Kwas metaniowy
  • Kyselina mravenci
  • Methanoate
  • Methanoic acid
  • Methanoic acid monomer
  • Mierenzuur
  • Myrmicyl
  • Sodium Formate
  • Sybest
  • Trisodium phosphonoformate hexahydrate
  • Wonderbond Hardener M 600L
  • Acide formique
  • H-COOH
  • HCO2H
  • Methoic acid
  • Methoate
  • Calcium formate
  • Cobalt(II) formate dihydrate
  • Formic acid, aluminum salt
  • Formic acid, copper salt
  • Formic acid, cromium (+3) salt
  • Lithium formate
  • Ammonium formate
  • Formic acid, ammonium (4:1) salt
  • Formic acid, ammonium salt
  • Formic acid, calcium salt
  • Formic acid, copper (+2) salt
  • Formic acid, lead (+2) salt
  • Formic acid, lead salt
  • Formic acid, nickel salt
  • Formic acid, potassium salt
  • Formic acid, strontium salt
  • Mafusol
  • Ammonium tetraformate
  • Formic acid, 14C-labeled
  • Formic acid, cobalt (+2) salt
  • Formic acid, copper, ammonium salt
  • Formic acid, sodium salt
  • Formic acid, sodium salt, 14C-labeled
  • Formic acid, ammonium (2:1) salt
  • Formic acid, cadmium salt
  • Formic acid, cesium salt
  • Formic acid, copper, nickel salt
  • Formic acid, cromium (+3), sodium (4:1:1) salt
  • Formic acid, lithium salt
  • Formic acid, magnesium salt
  • Formic acid, nickel (+2) salt
  • Formic acid, rubidium salt
  • Formic acid, sodium salt, 13C-labeled
  • Formic acid, thallium (+1) salt
  • Formic acid, zinc salt
  • Nickel formate dihydrate
  • Aluminum formate
  • Potassium formate
  • Strontium formate
  • Lead formate
  • Nickel formate
  • Chromic formate
  • Cobaltous formate
  • Cupric formate
  • Magnesium formate
  • Zinc formate
CAS number64-18-6
WeightAverage: 46.0254
Monoisotopic: 46.005479308
InChI KeyBDAGIHXWWSANSR-UHFFFAOYSA-N
InChIInChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
IUPAC Nameformic acid
Traditional IUPAC Nameformic acid
Chemical FormulaCH2O2
SMILES[H]OC([H])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point8.4 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)]PhysProp
LogP-0.54 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility477 g/LALOGPS
logP-0.47ALOGPS
logP-0.27ChemAxon
logS1.02ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.15 m³·mol⁻¹ChemAxon
Polarizability3.37 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondrion
Organoleptic Properties
Flavour/OdourSource
FormylFDB012804
PungentFDB012804
VinegarFDB012804
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glyoxylate and dicarboxylate metabolismec00630 Map00630
Methane metabolismec00680 Map00680
Nitrogen metabolismec00910 Map00910
Pyruvate metabolismec00620 Map00620
Riboflavin metabolismec00740 Map00740
SMPDB Reactions
1,2-Dihydroxy-3-keto-5-methylthiopentene + oxygen4-Methylthio-2-oxobutanoate + hydron + Formic acid
N10-Formyl-THF + ADP + phosphateAdenosine triphosphate + Formic acid + Tetrahydrofolic acid
GTP + waterFormic acid + hydron + 7,8-dihydroneopterin 3'-triphosphate
N'-Formylkynurenine + waterFormic acid + hydron + L-Kynurenine
GTP + waterFormic acid + Pyrophosphate + 2,5-Diamino-6-(1-D-ribosylamino)pyrimidin-4(3H)-one 5'-phosphate
KEGG Reactions
5-(methylsulfanyl)-2,3-dioxopentyl phosphate + waterhydron + 4-Methylthio-2-oxobutanoate + phosphate + Formic acid
D-ribulose 5-phosphateFormic acid + 2-Hydroxy-3-oxobutyl phosphate + hydron
oxygen + NADH + hydron + Lanosterinwater + Formic acid + NAD + 4,4-Dimethylcholesta-8,14,24-trienol
oxygen + hydron + NADPH + LanosterinNADP + water + Formic acid + 4,4-Dimethylcholesta-8,14,24-trienol
Ubiquinone-6 + Formic acid + hydronUbiquinol-6 + Carbon dioxide
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
14745 ± 737 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Jin, C., Barrientos, A., Tzagoloff, A. (2003). "Yeast dihydroxybutanone phosphate synthase, an enzyme of the riboflavin biosynthetic pathway, has a second unrelated function in expression of mitochondrial respiration." J Biol Chem 278:14698-14703.12595523
  • Subhi, A. L., Diegelman, P., Porter, C. W., Tang, B., Lu, Z. J., Markham, G. D., Kruger, W. D. (2003). "Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites." J Biol Chem 278:49868-49873.14506228
  • Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417
  • Lamb, D. C., Kelly, D. E., Manning, N. J., Kaderbhai, M. A., Kelly, S. L. (1999). "Biodiversity of the P450 catalytic cycle: yeast cytochrome b5/NADH cytochrome b5 reductase complex efficiently drives the entire sterol 14-demethylation (CYP51) reaction." FEBS Lett 462:283-288.10622712
Synthesis Reference: Finholt, Albert E.; Jacobson, Eugene C. The reduction of carbon dioxide to formic acid with lithium aluminum hydride. Journal of the American Chemical Society (1952), 74 3943-4.
External Links:
ResourceLink
CHEBI ID30751
HMDB IDHMDB00142
Pubchem Compound ID284
Kegg IDC00058
ChemSpider ID278
FOODB IDFDB012804
WikipediaFormic_acid
BioCyc IDFORMATE

Enzymes

General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L- tryptophan metabolite L-kynurenine to form kynurenic acid (KA)
Gene Name:
BNA3
Uniprot ID:
P47039
Molecular weight:
50081.89844
Reactions
L-kynurenine + 2-oxoglutarate → 4-(2-aminophenyl)-2,4-dioxobutanoate + L-glutamate.
General function:
Involved in iron ion binding
Specific function:
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
Gene Name:
ERG11
Uniprot ID:
P10614
Molecular weight:
60719.80078
Reactions
Obtusifoliol + 3 O(2) + 3 NADPH → 4-alpha-methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol + formate + 3 NADP(+) + 4 H(2)O.
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes the enolization of 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P) into the intermediate 2-hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (HK-MTPenyl-1-P), which is then dephosphorylated to form the acireductone 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene)
Gene Name:
UTR4
Uniprot ID:
P32626
Molecular weight:
25187.19922
Reactions
5-(methylthio)-2,3-dioxopentyl phosphate + H(2)O → 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + phosphate.
2-Phosphoglycolate + H2O → glycolate + phosphate
General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxylate = 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2)
Gene Name:
ADE2
Uniprot ID:
P21264
Molecular weight:
62338.69922
Reactions
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate → 5-amino-1-(5-phospho-D-ribosyl)imidazole + CO(2).
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH
Gene Name:
MIS1
Uniprot ID:
P09440
Molecular weight:
106216.0
Reactions
5,10-methylenetetrahydrofolate + NADP(+) → 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O → 10-formyltetrahydrofolate.
ATP + formate + tetrahydrofolate → ADP + phosphate + 10-formyltetrahydrofolate.
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH
Gene Name:
ADE3
Uniprot ID:
P07245
Molecular weight:
102204.0
Reactions
5,10-methylenetetrahydrofolate + NADP(+) → 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O → 10-formyltetrahydrofolate.
ATP + formate + tetrahydrofolate → ADP + phosphate + 10-formyltetrahydrofolate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Formate + NAD(+) = CO(2) + NADH
Gene Name:
FDH1
Uniprot ID:
Q08911
Molecular weight:
41714.0
Reactions
Formate + NAD(+) → CO(2) + NADH.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Formate + NAD(+) = CO(2) + NADH
Gene Name:
FDH2
Uniprot ID:
P0CF35
Molecular weight:
26487.19922
Reactions
Formate + NAD(+) → CO(2) + NADH.
General function:
Involved in GTP cyclohydrolase II activity
Specific function:
Catalyzes the conversion of GTP to 2,5-diamino-6- ribosylamino-4(3H)-pyrimidinone 5'-phosphate (DARP), formate and pyrophosphate
Gene Name:
RIB1
Uniprot ID:
P38066
Molecular weight:
38331.60156
Reactions
GTP + 3 H(2)O → formate + 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine + diphosphate.
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde
Gene Name:
Not Available
Uniprot ID:
P40363
Molecular weight:
33934.0
Reactions
S-formylglutathione + H(2)O → glutathione + formate.
4-methylumbelliferyl acetate + H2O → 4-methylumbelliferone + acetate
General function:
Involved in 3,4-dihydroxy-2-butanone-4-phosphate synthase activity
Specific function:
Catalyzes the conversion of D-ribulose 5-phosphate to formate and 3,4-dihydroxy-2-butanone 4-phosphate
Gene Name:
RIB3
Uniprot ID:
Q99258
Molecular weight:
22567.40039
Reactions
D-ribulose 5-phosphate → formate + L-3,4-dihydroxybutan-2-one 4-phosphate.
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L- kynurenine, the second step in the conversion of tryptophan to nicotinic acid, NAD(H) and NADP(H)
Gene Name:
BNA7
Uniprot ID:
Q04066
Molecular weight:
29991.0
Reactions
N-formyl-L-kynurenine + H(2)O → formate + L-kynurenine.
General function:
Involved in GTP cyclohydrolase I activity
Specific function:
GTP + H(2)O = formate + 2-amino-4-hydroxy-6- (erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphate
Gene Name:
FOL2
Uniprot ID:
P51601
Molecular weight:
27768.80078
Reactions
GTP + H(2)O → formate + 2-amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)-dihydropteridine triphosphate.