Formic acid (YMDB00385)

Identification

YMDB ID

YMDB00385

Name

Formic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Formic acid, also known as formate or ameisensaeure, 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. Formic acid is a weakly acidic compound (based on its pKa). Formic acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

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 number

64-18-6

Weight

Average: 46.0254
Monoisotopic: 46.005479308

InChI Key

BDAGIHXWWSANSR-UHFFFAOYSA-N

InChI

InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)

IUPAC Name

formic acid

Traditional IUPAC Name

formic acid

Chemical Formula

CH₂O₂

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:30751 )
Straight chain fatty acids (C00058 )
Saturated fatty acids (C00058 )

Physical Properties

State

Liquid

Charge

Melting point

8.4 °C

Experimental Properties

Property	Value	Reference
Water Solubility	1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)]	PhysProp
LogP	-0.54 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	477 g/L	ALOGPS
logP	-0.47	ALOGPS
logP	-0.27	ChemAxon
logS	1.02	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	8.15 m³·mol⁻¹	ChemAxon
Polarizability	3.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondrion

Organoleptic Properties

Flavour/Odour	Source
Formyl	FDB012804
Pungent	FDB012804
Vinegar	FDB012804

SMPDB Pathways

Cholesterol biosynthesis and metabolism CE(10:0)	PW002545
Cholesterol biosynthesis and metabolism CE(12:0)	PW002548
Cholesterol biosynthesis and metabolism CE(14:0)	PW002544
Cholesterol biosynthesis and metabolism CE(16:0)	PW002550
Cholesterol biosynthesis and metabolism CE(18:0)	PW002551

KEGG Pathways

Glyoxylate and dicarboxylate metabolism	ec00630
Methane metabolism	ec00680
Nitrogen metabolism	ec00910
Pyruvate metabolism	ec00620
Riboflavin metabolism	ec00740

SMPDB Reactions

KEGG Reactions

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
14745 ± 737 µM	YEB media with 0.5 mM glucose	aerobic	Baker's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-5d27bb312e37a2c8994f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fmi-9200000000-2a89ba98485194acd75a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-0002-9000000000-a8fbddf8ca4197b30013	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-0002-9000000000-98310116f8a2d6a969ce	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-0002-9000000000-ec8753fd9790a3cf0be8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-0002-9000000000-121d1a025b72a70e412a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0002-9000000000-5f1955dee7ab988e86dd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-0002-9000000000-f8e14272296ee06d19f4	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-92190863fc6ae28a8789	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-92190863fc6ae28a8789	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-348f481062f48991a0aa	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-004j-9000000000-2e63b0c1e2e417b0d747	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	30751
HMDB ID	HMDB00142
Pubchem Compound ID	284
Kegg ID	C00058
ChemSpider ID	278
FOODB ID	FDB012804
Wikipedia	Formic_acid
BioCyc ID	FORMATE

Enzymes

Protein Details

1. Probable kynurenine--oxoglutarate transaminase BNA3

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.

Protein Details

2. Lanosterol 14-alpha demethylase

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.

Protein Details

3. Enolase-phosphatase E1

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

Protein Details

4. Phosphoribosylaminoimidazole carboxylase

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).

Protein Details

5. C-1-tetrahydrofolate synthase, mitochondrial

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.

Protein Details

6. C-1-tetrahydrofolate synthase, cytoplasmic

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.

Protein Details

7. Formate dehydrogenase 1

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.

Protein Details

8. Putative formate dehydrogenase 2

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.

Protein Details

9. GTP cyclohydrolase-2

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.

Protein Details

10. S-formylglutathione hydrolase

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

Protein Details

11. 3,4-dihydroxy-2-butanone 4-phosphate synthase

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.

Protein Details

12. Probable kynurenine formamidase

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.

Protein Details

13. GTP cyclohydrolase 1

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.

Structure for #<Compound:0xa8475c7c>

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