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Record Information
Version1.0
Creation Date2016-09-30 22:20:06 UTC
Update Date2020-06-02 18:13:54 UTC
BMDB IDBMDB0000142
Secondary Accession Numbers
  • BMDB00142
Metabolite Identification
Common NameFormic acid
DescriptionFormic 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 exists as a liquid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Formic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
Acide formiqueChEBI
AmeisensaeureChEBI
Aminic acidChEBI
BilorinChEBI
Formylic acidChEBI
H-COOHChEBI
HCO2HChEBI
HCOOHChEBI
Hydrogen carboxylic acidChEBI
Methanoic acidChEBI
Methoic acidChEBI
AminateGenerator
FormylateGenerator
Hydrogen carboxylateGenerator
MethanoateGenerator
MethoateGenerator
FormateGenerator
Add-FHMDB
AmeisensaureHMDB
Collo-bueglattHMDB
Collo-didaxHMDB
FormiraHMDB
FormisotonHMDB
Methanoic acid monomerHMDB
MyrmicylHMDB
Sodium formateHMDB
SybestHMDB
Wonderbond hardener m 600lHMDB
Calcium formateHMDB
Cobalt(II) formate dihydrateHMDB
Formic acid, aluminum saltHMDB
Formic acid, copper saltHMDB
Formic acid, cromium (+3) saltHMDB
Lithium formateHMDB
Ammonium formateHMDB
Formic acid, ammonium (4:1) saltHMDB
Formic acid, ammonium saltHMDB
Formic acid, calcium saltHMDB
Formic acid, copper (+2) saltHMDB
Formic acid, lead (+2) saltHMDB
Formic acid, lead saltHMDB
Formic acid, nickel saltHMDB
Formic acid, potassium saltHMDB
Formic acid, strontium saltHMDB
MafusolHMDB
Ammonium tetraformateHMDB
Formic acid, 14C-labeledHMDB
Formic acid, cobalt (+2) saltHMDB
Formic acid, copper, ammonium saltHMDB
Formic acid, sodium saltHMDB
Formic acid, sodium salt, 14C-labeledHMDB
Formic acid, ammonium (2:1) saltHMDB
Formic acid, cadmium saltHMDB
Formic acid, cesium saltHMDB
Formic acid, copper, nickel saltHMDB
Formic acid, cromium (+3), sodium (4:1:1) saltHMDB
Formic acid, lithium saltHMDB
Formic acid, magnesium saltHMDB
Formic acid, nickel (+2) saltHMDB
Formic acid, rubidium saltHMDB
Formic acid, sodium salt, 13C-labeledHMDB
Formic acid, thallium (+1) saltHMDB
Formic acid, zinc saltHMDB
Nickel formate dihydrateHMDB
Aluminum formateHMDB
Potassium formateHMDB
Strontium formateHMDB
Lead formateHMDB
Nickel formateHMDB
Chromic formateHMDB
Cobaltous formateHMDB
Cupric formateHMDB
Magnesium formateHMDB
Zinc formateHMDB
Chemical FormulaCH2O2
Average Molecular Weight46.0254
Monoisotopic Molecular Weight46.005479308
IUPAC Nameformic acid
Traditional Nameformic acid
CAS Registry Number64-18-6
SMILES
OC=O
InChI Identifier
InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
InChI KeyBDAGIHXWWSANSR-UHFFFAOYSA-N
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
  • Nucleus
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point8.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP-0.54HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-5d27bb312e37a2c8994fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fmi-9200000000-2a89ba98485194acd75aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-004j-9000000000-2e63b0c1e2e417b0d747View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • Blood
  • Brain
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Muscle
  • Neuron
  • Pancreas
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified78 +/- 12 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified1686 +/- 209 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Longissimus Thoracis MuscleDetected and Quantified533 +/- 316 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
MilkDetected and Quantified15.9 (3.3 - 24) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified117.40 +/- 1.66 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12.9 (1.9 - 28) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified17.7 (4.3 - 46) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified160 (103 - 380) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified15 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified16 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15.6 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified16 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified116.44 +/- 1.93 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified115.20 +/- 2.75 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified110 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified160 +/- 46 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified60-655 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified110-123 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified337 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified320 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified258 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified321 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified20 +/- 4 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Ruminal FluidDetected and Quantified159.7 +/- 45.8 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified162.9 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified158.8 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified275.7 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified159.7 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified163 +/- 33 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified160 +/- 45 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified276 +/- 104 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Semimembranosus MuscleDetected and Quantified723 +/- 184 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
TestisDetected and Quantified823 +/- 240 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
Ruminal FluidDetected and Quantified275.71 +/- 294.47 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000142
DrugBank IDDB01942
Phenol Explorer Compound IDNot Available
FooDB IDFDB012804
KNApSAcK IDC00001182
Chemspider IDNot Available
KEGG Compound IDC00058
BioCyc IDFORMATE
BiGG IDNot Available
Wikipedia LinkFormic_acid
METLIN IDNot Available
PubChem Compound284
PDB IDNot Available
ChEBI ID30751
References
Synthesis ReferenceFinholt, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  2. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  3. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively. Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid. Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen. Also displays 2-hydroxylase activity toward estrone. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP19A1
Uniprot ID:
P46194
Molecular weight:
58090.0
Reactions
19-Oxotestosterone + Oxygen + Reduced flavoprotein → Estradiol + Formic acid + Oxidized flavoproteindetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in sterol biosynthesis. Catalyzes 14-alpha demethylation of lanosterol and 24,25-dihydrolanosterol likely through sequential oxidative conversion of 14-alpha methyl group to hydroxymethyl, then to carboxylaldehyde, followed by the formation of the delta 14,15 double bond in the sterol core and concomitant release of formic acid. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP51A1
Uniprot ID:
Q4PJW3
Molecular weight:
56596.0
Reactions
Lanosterin + 3 Oxygen + 3 NADPH → 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid +3 NADP +4 Waterdetails
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:
ESD
Uniprot ID:
Q08E20
Molecular weight:
31548.0
General function:
Nucleotide transport and metabolism
Specific function:
May provide the missing metabolic reaction required to link the mitochondria and the cytoplasm in the mammalian model of one-carbon folate metabolism in embryonic an transformed cells complementing thus the enzymatic activities of MTHFD2.
Gene Name:
MTHFD1L
Uniprot ID:
Q0VCR7
Molecular weight:
105227.0
General function:
Involved in protein binding
Specific function:
Mediates tetrahydrobiopterin inhibition of GTP cyclohydrolase 1. This inhibition is reversed by L-phenylalanine (By similarity).
Gene Name:
GCHFR
Uniprot ID:
Q32L41
Molecular weight:
9557.0
Reactions
Formamidopyrimidine nucleoside triphosphate + Water → 2,5-Diaminopyrimidine nucleoside triphosphate + Formic aciddetails
Guanosine triphosphate + Water → Formamidopyrimidine nucleoside triphosphate + Formic aciddetails
General function:
Inorganic ion transport and metabolism
Specific function:
Not Available
Gene Name:
SLC26A6
Uniprot ID:
Q08DQ8
Molecular weight:
83332.0
General function:
Not Available
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites.
Gene Name:
AFMID
Uniprot ID:
E1BLL5
Molecular weight:
35460.0
Reactions
N'-Formylkynurenine + Water → L-Kynurenine + Formic aciddetails
Formylanthranilic acid + Water → 2-Aminobenzoic acid + Formic aciddetails
5-Hydroxy-N-formylkynurenine + Water → 5-Hydroxykynurenine + Formic aciddetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
GCH1
Uniprot ID:
F1MZ14
Molecular weight:
27726.0
Reactions
Formamidopyrimidine nucleoside triphosphate + Water → 2,5-Diaminopyrimidine nucleoside triphosphate + Formic aciddetails
Guanosine triphosphate + Water → Formamidopyrimidine nucleoside triphosphate + Formic aciddetails