P. aeruginosa Metabolome Database: Formaldehyde (PAMDB000382)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000382

Identification

Name:

Formaldehyde

Description:

Formaldehyde is a highly reactive aldehyde gas. It is the simplest aldehyde. Its chemical formula is H2CO. Although formaldehyde is a gas at room temperature, it is readily soluble in water, and it is most commonly sold as a 37% solution in water called by trade names such as formalin or formol. In water, formaldehyde polymerizes, and formalin actually contains very little formaldehyde in the form of H2CO monomer. Formaldehyde exhibits most of the general chemical properties of the aldehydes, except that is generally more reactive than other aldehydes. Formaldehyde is a potent electrophile. It can participate in electrophilic aromatic substitution reactions with aromatic compounds and can undergo electrophilic addition reactions with alkenes. In Pseudomonas aeruginosa, formaldehyde is formed by the breakdown of N-methyltryptophan and FMNH by their corresponding oxidases.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Aldeide formica
Chlodithan
Chlodithane
Fannoform
Formaldehyde
Formalin
Formalina
Formaline
Formalith
Formic aldehyde
Formol
Methaldehyde
Methanal
Methylene glycol
Methylene oxide
Oxomethylene
Paraform

Chemical Formula:

CH₂O

Average Molecular Weight:

30.026

Monoisotopic Molecular Weight:

30.010564686

InChI Key:

WSFSSNUMVMOOMR-UHFFFAOYSA-N

InChI:

InChI=1S/CH2O/c1-2/h1H2

CAS number:

50-00-0

IUPAC Name:

formaldehyde

Traditional IUPAC Name:

formaldehyde

SMILES:

C=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as hydrocarbon derivatives. These are derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. THey contain at least one carbon atom and heteroatom.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Hydrocarbon derivatives

Alternative Parents

Aldehydes

Substituents

Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:16842 )
aldehyde (CHEBI:16842 )
an <i>n</i>-alkanal (FORMALDEHYDE )

Physical Properties

State:

Liquid

Charge:

Melting point:

-92 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	400 mg/mL at 20 oC [PICKRELL,JA et al. (1983)]	PhysProp
LogP:	0.35 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	198.0 mg/mL	ALOGPS
logP	-0.68	ALOGPS
logP	-0.47	ChemAxon
logS	0.82	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	6.31 m³·mol^-1	ChemAxon
Polarizability	2.58 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

Reactions:

FMNH + Methanesulfonate + Oxygen > Formaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite
Water + Oxygen + Sarcosine > Formaldehyde + Glycine + Hydrogen peroxide
N-Methyltryptophan + Water + Oxygen > Formaldehyde + Hydrogen peroxide + L-Tryptophan
Formaldehyde + Glutathione <> S-(Hydroxymethyl)glutathione
Methanol + Hydrogen peroxide <> Formaldehyde +2 Water
Formaldehyde + Tetrahydrofolic acid > 5,10-Methylene-THF + Water
a methylated nucleobase within DNA + Oxygen + Oxoglutaric acid Hydrogen ion + a nucleobase within DNA + Carbon dioxide + Formaldehyde + Succinic acid
N1-Methyladenine + Oxygen + Oxoglutaric acid > Hydrogen ion + Adenine + Carbon dioxide + Formaldehyde + Succinic acid
N3-Methylcytosine + Oxygen + Oxoglutaric acid > Hydrogen ion + Cytosine + Carbon dioxide + Formaldehyde + Succinic acid
DNA-base-CH(3) + Oxoglutaric acid + Oxygen > DNA-base + Formaldehyde + Succinic acid + Carbon dioxide

Pathways:

Chloroalkane and chloroalkene degradation pae00625
Methane metabolism pae00680
Microbial metabolism in diverse environments pae01120

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-793a330f9e6c7661e86d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-793a330f9e6c7661e86d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-793a330f9e6c7661e86d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-5ea4ad4bdb0565b737bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-5ea4ad4bdb0565b737bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-5ea4ad4bdb0565b737bb	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-004i-9000000000-58b4df664ee160d1f943	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available

References

References:

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Castrillon DH, Sun D, Weremowicz S, Fisher RA, Crum CP, Genest DR: Discrimination of complete hydatidiform mole from its mimics by immunohistochemistry of the paternally imprinted gene product p57KIP2. Am J Surg Pathol. 2001 Oct;25(10):1225-30. Pubmed: 11688455
Heck H, Casanova M: The implausibility of leukemia induction by formaldehyde: a critical review of the biological evidence on distant-site toxicity. Regul Toxicol Pharmacol. 2004 Oct;40(2):92-106. Pubmed: 15450713
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Katsetos CD, Jami MM, Krishna L, Jackson R, Patchefsky AS, Cooper HS: Novel immunohistochemical localization of 28,000 molecular-weight (Mr) calcium binding protein (calbindin-D28k) in enterochromaffin cells of the human appendix and neuroendocrine tumors (carcinoids and small-cell carcinomas) of the midgut and foregut. Arch Pathol Lab Med. 1994 Jun;118(6):633-9. Pubmed: 8204010
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Koscielny J, Aslan T, Meyer O, Kiesewetter H, Jung F, Mrowietz C, Latza R: Use of the platelet reactivity index by Grotemeyer, platelet function analyzer, and retention test Homburg to monitor therapy with antiplatelet drugs. Semin Thromb Hemost. 2005;31(4):464-9. Pubmed: 16149025
Lu CY, Chou AK, Wu CL, Yang CH, Chen JT, Wu PC, Lin SH, Muhammad R, Yang LC: Gene-gun particle with pro-opiomelanocortin cDNA produces analgesia against formalin-induced pain in rats. Gene Ther. 2002 Aug;9(15):1008-14. Pubmed: 12101431
Marinkovic S, Gibo H, Zelic O, Nikodijevic I: The neurovascular relationships and the blood supply of the trochlear nerve: surgical anatomy of its cisternal segment. Neurosurgery. 1996 Jan;38(1):161-9. Pubmed: 8747965
Moore GR, Leung E, MacKay AL, Vavasour IM, Whittall KP, Cover KS, Li DK, Hashimoto SA, Oger J, Sprinkle TJ, Paty DW: A pathology-MRI study of the short-T2 component in formalin-fixed multiple sclerosis brain. Neurology. 2000 Nov 28;55(10):1506-10. Pubmed: 11094105
Nader N, Raverot G, Emptoz-Bonneton A, Dechaud H, Bonnay M, Baudin E, Pugeat M: Mitotane has an estrogenic effect on sex hormone-binding globulin and corticosteroid-binding globulin in humans. J Clin Endocrinol Metab. 2006 Jun;91(6):2165-70. Epub 2006 Mar 21. Pubmed: 16551731
North WG, Memoli VA, Keegan BP: Immunohistochemical detection of NRSA on small cell lung cancer with a monoclonal antibody (MAG-1) that recognizes the carboxyl terminus of provasopressin. Appl Immunohistochem Mol Morphol. 2005 Dec;13(4):363-6. Pubmed: 16280667
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Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	16842
HMDB ID	HMDB01426
Pubchem Compound ID	712
Kegg ID	C00067
ChemSpider ID	692
Wikipedia	Formaldehyde
BioCyc ID	FORMALDEHYDE
EcoCyc ID	FORMALDEHYDE
Ligand Expo	FOR

Enzymes

Protein Details

• Catalase HPII

General function:: Involved in catalase activity
Specific function:: Decomposes hydrogen peroxide into water and oxygen; serves to protect cells from the toxic effects of hydrogen peroxide
Gene Name:: katE
Locus Tag:: PA2147
Molecular weight:: 78 kDa

Reactions

2 H(2)O(2) = O(2) + 2 H(2)O.

Protein Details

• FMN reductase

General function:: Involved in FMN reductase activity
Specific function:: Catalyzes an NAD(P)H-dependent reduction of FMN, but is also able to reduce FAD or riboflavin
Gene Name:: ssuE
Locus Tag:: PA3446
Molecular weight:: 21.5 kDa

Reactions

FMNH(2) + NADP(+) = FMN + NADPH.

Protein Details

• Alkanesulfonate monooxygenase

General function:: Involved in alkanesulfonate monooxygenase activity
Specific function:: Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:: ssuD
Locus Tag:: PA3444
Molecular weight:: 41.6 kDa

Reactions

An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.

Formaldehyde (PAMDB000382)

Structure for Formaldehyde (PAMDB000382)

Enzymes

Reactions

Reactions

Reactions

Transporters