Showing Compound Formic acid (FDB012804)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:22 UTC

Update date

2024-11-29 22:27:54 UTC

Primary ID

FDB012804

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Formic acid

Description

Formic acid, also known as methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts, and the anion derived from formic acid are called formates. Industrially, formic acid is produced through the oxidation of methanol. 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 by-product 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).

CAS Number

64-18-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Acide formique	ChEBI
Ameisensaeure	ChEBI
Aminic acid	ChEBI
Bilorin	ChEBI
Formylic acid	ChEBI
H-COOH	ChEBI
HCO2H	ChEBI
HCOOH	ChEBI
Hydrogen carboxylic acid	ChEBI
Methanoic acid	ChEBI
Methoic acid	ChEBI
Aminate	Generator
Formylate	Generator
Hydrogen carboxylate	Generator
Methanoate	Generator
Methoate	Generator
Formate	Generator
Add-F	HMDB
Ameisensaure	HMDB
Collo-bueglatt	HMDB
Collo-didax	HMDB
Formira	HMDB
Formisoton	HMDB
Methanoic acid monomer	HMDB
Myrmicyl	HMDB
Sodium formate	HMDB
Sybest	HMDB
Wonderbond hardener m 600l	HMDB
Calcium formate	HMDB
Cobalt(II) formate dihydrate	HMDB
Formic acid, aluminum salt	HMDB
Formic acid, copper salt	HMDB
Formic acid, cromium (+3) salt	HMDB
Lithium formate	HMDB
Ammonium formate	HMDB
Formic acid, ammonium (4:1) salt	HMDB
Formic acid, ammonium salt	HMDB
Formic acid, calcium salt	HMDB
Formic acid, copper (+2) salt	HMDB
Formic acid, lead (+2) salt	HMDB
Formic acid, lead salt	HMDB
Formic acid, nickel salt	HMDB
Formic acid, potassium salt	HMDB
Formic acid, strontium salt	HMDB
Mafusol	HMDB
Ammonium tetraformate	HMDB
Formic acid, 14C-labeled	HMDB
Formic acid, cobalt (+2) salt	HMDB
Formic acid, copper, ammonium salt	HMDB
Formic acid, sodium salt	HMDB
Formic acid, sodium salt, 14C-labeled	HMDB
Formic acid, ammonium (2:1) salt	HMDB
Formic acid, cadmium salt	HMDB
Formic acid, cesium salt	HMDB
Formic acid, copper, nickel salt	HMDB
Formic acid, cromium (+3), sodium (4:1:1) salt	HMDB
Formic acid, lithium salt	HMDB
Formic acid, magnesium salt	HMDB
Formic acid, nickel (+2) salt	HMDB
Formic acid, rubidium salt	HMDB
Formic acid, sodium salt, 13C-labeled	HMDB
Formic acid, thallium (+1) salt	HMDB
Formic acid, zinc salt	HMDB
Nickel formate dihydrate	HMDB
Aluminum formate	HMDB
Potassium formate	HMDB
Strontium formate	HMDB
Lead formate	HMDB
Nickel formate	HMDB
Chromic formate	HMDB
Cobaltous formate	HMDB
Cupric formate	HMDB
Magnesium formate	HMDB
Zinc formate	HMDB
Amasil	biospider
FEMA 2487	db_source
Wonderbond hardener m 600L	HMDB

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

CH2O2

IUPAC name

formic acid

InChI Identifier

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

InChI Key

BDAGIHXWWSANSR-UHFFFAOYSA-N

Isomeric SMILES

OC=O

Average Molecular Weight

46.0254

Monoisotopic Molecular Weight

46.005479308

Classification

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 )

Ontology

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Environmental contaminant

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 26.10%; H 4.38%; O 69.52%	DFC
Melting Point	Mp 8.4°	DFC
Boiling Point	Bp120 50°	DFC
Experimental Water Solubility	1000 mg/mL at 25 oC	RIDDICK,JA et al. (1986)
Experimental logP	-0.54	HANSCH,C ET AL. (1995)
Experimental pKa	3.744
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 1.22	DFC
Refractive Index	n20D 1.3714	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004j-9000000000-2e63b0c1e2e417b0d747	2015-03-01	View Spectrum
Predicted GC-MS	Formic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9000000000-5d27bb312e37a2c8994f	Spectrum
Predicted GC-MS	Formic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fmi-9200000000-2a89ba98485194acd75a	Spectrum
Predicted GC-MS	Formic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Formic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-0002-9000000000-a8fbddf8ca4197b30013	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-0002-9000000000-98310116f8a2d6a969ce	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-0002-9000000000-ec8753fd9790a3cf0be8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-0002-9000000000-121d1a025b72a70e412a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0002-9000000000-5f1955dee7ab988e86dd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-0002-9000000000-f8e14272296ee06d19f4	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-92190863fc6ae28a8789	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-92190863fc6ae28a8789	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-348f481062f48991a0aa	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB01942

HMDB ID

HMDB00142

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1008401

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Acaricide	22153	An agent that kills mites and ticks, used to control infestations and prevent diseases like scabies and tick-borne illnesses. Therapeutically, acaricides are applied topically or systemically to treat parasitic infections, reducing discomfort and preventing disease transmission. Key medical uses include treating acariasis, demodectic mange, and tick paralysis.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-syncopic		An agent that relieves symptoms of fainting, such as low heart rate, low blood pressure, or low blood flow to the brain, playing a biological role in regulating cardiovascular and neurological functions, with therapeutic applications in managing syncope and key medical uses in treating orthostatic hypotension and preventing fainting episodes.	DUKE
Astringent	74783	An agent that constricts or shrinks tissues, reducing bleeding and inflammation. It plays a biological role in wound healing and has therapeutic applications in treating hemorrhoids, diarrhea, and skin irritations. Key medical uses include reducing swelling, stopping bleeding, and protecting mucous membranes, making it useful in various topical and oral preparations.	DUKE
Corrosive		A substance that destroys or damages materials, including living tissue, causing chemical burns upon contact. It has no therapeutic applications or biological role, but is used in industrial processes. In medicine, corrosives are avoided due to their harmful effects, and treatment focuses on managing chemical burn injuries caused by exposure.	DUKE
Counterirritant		An agent that induces mild irritation or inflammation in one area to reduce discomfort and/or inflammation in another, often used to relieve pain, reduce swelling, and promote healing in conditions like arthritis, sprains, and strains.	DUKE
Name	48318	flavor	DUKE
Fungistat		An agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients.	DUKE
Fungitoxic	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it has applications in treating fungal diseases. Key medical uses include managing fungal infections, such as athlete's foot, ringworm, and candidiasis, as well as preventing fungal growth in immunocompromised patients.	DUKE
Irritant		An agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Preservative	65255	An agent that prevents spoilage and extends shelf life, playing a biological role in inhibiting microbial growth. Therapeutically, preservatives are used to prevent contamination and degradation of pharmaceuticals, cosmetics, and food products, ensuring safety and efficacy. Key medical uses include sterilization and stabilization of medical preparations, such as vaccines, ointments, and injectables.	DUKE
Toxic	52209	A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	CHEBI

Enzymes

Name	Gene Name	UniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	A0N0X8
Cytochrome P450 2D6	CYP2D6	Q6NWU0
S-formylglutathione hydrolase	ESD	P10768
Aspartoacylase	ASPA	P45381
Aspartoacylase-2	ACY3	Q96HD9
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase	ADI1	Q9BV57
C-1-tetrahydrofolate synthase, cytoplasmic	MTHFD1	P11586
Peptide deformylase, mitochondrial	PDF	Q9HBH1
Monofunctional C1-tetrahydrofolate synthase, mitochondrial	MTHFD1L	Q6UB35
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	MTHFD2	Q7Z650

Pathways

Name	SMPDB Link	KEGG Link
Folate Metabolism	SMP00053	map00670
Pterine Biosynthesis	SMP00005	map00790
Metabolism and Physiological Effects of Kynurenine	SMP0125524	Not Available
Metabolism and Physiological Effects of 2-Aminobenzoic acid	SMP0126869	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
pungent	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vinegar	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
formyl	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.