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Record Information

Version

2.0

Creation Date

2012-05-31 14:04:48 -0600

Update Date

2015-06-03 15:54:43 -0600

Secondary Accession Numbers

ECMDB04092

Identification

Name:

alpha-Ketoisovaleric acid

Description

Alpha-ketoisovaleric acid is a branched chain organic acid which is a precursor to leucine and valine synthesis. It is also a degradation product from valine. The enzyme dihydroxy-acid dehydratase catalyzes the fourth step in the biosynthesis of isoleucine and valine, through the dehydration of 2, 3-dihydroxy-isovaleic acid into alpha-ketoisovaleric acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

α-keto-isovalerate
α-keto-isovaleric acid
α-keto-valine
α-ketoisopentanoate
α-ketoisopentanoic acid
α-ketovaline
α-oxoisovalerate
α-oxoisovaleric acid
2-Keto-3-Methylbutyrate
2-Keto-3-Methylbutyric acid
2-Keto-isovalerate
2-Keto-isovaleric acid
2-Ketoisovalerate
2-Ketoisovaleric acid
2-Ketoisvalerate
2-ketoisvaleric acid
2-Ketovaline
2-KIV
2-Oxo-3-methyl-butyrate
2-oxo-3-Methyl-butyric acid
2-Oxo-3-methylbutanoate
2-Oxo-3-methylbutanoic acid
2-Oxo-3-methylbutyrate
2-Oxo-3-methylbutyric acid
2-Oxoisopentanoate
2-Oxoisopentanoic acid
2-Oxoisovalerate
2-Oxoisovaleric acid
3-Methyl-2-oxo-Butanoate
3-Methyl-2-oxo-Butanoic acid
3-Methyl-2-oxo-Butyrate
3-Methyl-2-oxo-Butyric acid
3-Methyl-2-oxobutanoate
3-Methyl-2-oxobutanoic acid
3-Methyl-2-oxobutinoate
3-Methyl-2-oxobutinoic acid
3-Methyl-2-oxobutyrate
3-Methyl-2-oxobutyric acid
A-Keto-b-Methylbutyrate
A-Keto-b-Methylbutyric acid
A-Keto-Isovalerate
A-Keto-Isovaleric acid
a-keto-Valine
a-Ketoisopentanoate
a-Ketoisopentanoic acid
a-Ketoisovalerate
a-Ketoisovaleric acid
a-Ketovaline
A-Oxo-b-methylbutyrate
A-Oxo-b-methylbutyric acid
A-Oxoisovalerate
A-Oxoisovaleric acid
Alpha-Keto-beta-Methylbutyrate
Alpha-Keto-beta-Methylbutyric acid
Alpha-Keto-Isovalerate
Alpha-Keto-Isovaleric acid
Alpha-Keto-valine
Alpha-Ketoisopentanoate
Alpha-Ketoisopentanoic acid
Alpha-Ketoisovalerate
Alpha-Ketoisovaleric acid
Alpha-Ketovaline
Alpha-Oxo-beta-methylbutyrate
Alpha-Oxo-beta-methylbutyric acid
Alpha-Oxoisovalerate
Alpha-Oxoisovaleric acid
Dimethylpyruvate
Dimethylpyruvic acid
Isopropylglyoxylate
Isopropylglyoxylic acid
Ketovaline
α-keto-Isovalerate
α-keto-Isovaleric acid
α-keto-Valine
α-keto-β-Methylbutyrate
α-keto-β-Methylbutyric acid
α-Ketoisopentanoate
α-Ketoisopentanoic acid
α-Ketoisovalerate
α-Ketoisovaleric acid
α-Ketovaline
α-oxo-β-Methylbutyrate
α-oxo-β-Methylbutyric acid
α-Oxoisovalerate
α-Oxoisovaleric acid

Chemical Formula:

C₅H₈O₃

Weight:

Average: 116.1152
Monoisotopic: 116.047344122

InChI Key:

QHKABHOOEWYVLI-UHFFFAOYSA-N

InChI:

InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)

CAS number:

759-05-7

IUPAC Name:

3-methyl-2-oxobutanoic acid

Traditional IUPAC Name:

α-ketoisovalerate

SMILES:

CC(C)C(=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Branched fatty acid
Methyl-branched fatty acid
Short-chain keto acid
Alpha-keto acid
Fatty acyl
Alpha-hydroxy ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:16530 )
Branched fatty acids (C00141 )
Branched fatty acids (LMFA01020274 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

31.5 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	0.1 g/mL MeOH hot clear	PhysProp
LogP:	0.329	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	30.2 g/L	ALOGPS
logP	0.49	ALOGPS
logP	1.31	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	27.19 m³·mol⁻¹	ChemAxon
Polarizability	11.04 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:

SMPDB Pathways:

Pantothenate and CoA biosynthesis

PW000828

KEGG Pathways:

Pantothenate and CoA biosynthesis ec00770
Valine, leucine and isoleucine biosynthesis ec00290
Valine, leucine and isoleucine degradation ec00280

EcoCyc Pathways:

alanine biosynthesis I ALANINE-VALINESYN-PWY
isoleucine biosynthesis I (from threonine) LEUSYN-PWY
phosphopantothenate biosynthesis I PANTO-PWY
valine biosynthesis VALSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-9500000000-ff936b879a69b5d118f8	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-8920000000-e37b37d64d43dcf763f0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9400000000-e3995acc4818a98d0f48	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0f79-9720000000-5d89487273e44ea61a68	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9700000000-209c737dcac7df2b198c	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f79-5920000000-759a2f01b4f52767ade2	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9500000000-ff936b879a69b5d118f8	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-8920000000-e37b37d64d43dcf763f0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9400000000-e3995acc4818a98d0f48	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f79-9720000000-5d89487273e44ea61a68	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-7900000000-7e325567183fb56996d5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ufr-0930000000-be90b06add7135b4a539	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9000000000-52f9d8fc8386e4c512fe	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9600000000-52aefdc997dac92c8459	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-10ab58a33e9ca7dbace0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-ad51ff01c94b6046ad64	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-9993174a7b1801b90ddb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00xr-9500000000-293818b81e0879b6feb2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-75058f27a2178b9cf121	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-4c20af39e8ee009d5278	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-9993174a7b1801b90ddb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00xr-9500000000-1a58c6a6b4f5477dabdd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-75058f27a2178b9cf121	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-cc4465a47e663be66df5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-00di-9100000000-19511890852fce513a02	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9300000000-30d3bdfb6d38dbb8e101	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000l-9000000000-879b6502ff380673b776	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0159-9800000000-0cf4d3a0e7b3356995c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014o-9900000000-f35430a2eaea0d81df32	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r2-9400000000-21f8c3fae79161c82099	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-5f25e41413738bb6b5d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-801af00dea93fcfd637d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-8900000000-5185c7dfc72c25069904	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-9200000000-7e2a275a65197f96f5d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0600-9000000000-0013e0ff06f9896a1337	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-6900000000-7f00871b074cbd9a42e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06di-9400000000-6d56778068e11e4f8e85	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-b445e7fc67a8ff2bd3ba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-9000000000-733fb7227d2d053b112f	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Chuang DT, Niu WL, Cox RP: Activities of branched-chain 2-oxo acid dehydrogenase and its components in skin fibroblasts from normal and classical-maple-syrup-urine-disease subjects. Biochem J. 1981 Oct 15;200(1):59-67. Pubmed: 6895847
Gallina DL, Dominguez JM, Hoschoian JC, Barrio JR: Maintenance of nitrogen balance in a young woman by substitution of -ketoisovaleric acid for valine. J Nutr. 1971 Sep;101(9):1165-7. Pubmed: 5096137
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
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
Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. Pubmed: 9869358
Livesey G, Lund P: Binding of branched-chain 2-oxo acids to bovine serum albumin. Biochem J. 1982 Apr 15;204(1):265-72. Pubmed: 7115325
Schaefer K, von Herrath D, Erley CM, Asmus G: Calcium ketovaline as new therapy for uremic hyperphosphatemia. Miner Electrolyte Metab. 1990;16(6):362-4. Pubmed: 2089249
Schauder P, Schroder K, Langenbeck U: Serum branched-chain amino and keto acid response to a protein-rich meal in man. Ann Nutr Metab. 1984;28(6):350-6. Pubmed: 6393856
Shigematsu Y, Kikuchi K, Momoi T, Sudo M, Kikawa Y, Nosaka K, Kuriyama M, Haruki S, Sanada K, Hamano N, et al.: Organic acids and branched-chain amino acids in body fluids before and after multiple exchange transfusions in maple syrup urine disease. J Inherit Metab Dis. 1983;6(4):183-9. Pubmed: 6422161
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
Tsuchiya H, Hashizume I, Tokunaga T, Tatsumi M, Takagi N, Hayashi T: High-performance liquid chromatography of alpha-keto acids in human saliva. Arch Oral Biol. 1983;28(11):989-92. Pubmed: 6581765
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Pirrung, Michael C.; Ha, Hyun Joon; Holmes, Christopher P. Purification and inhibition of spinach a,b-dihydroxyacid dehydratase . Journal of Organic Chemistry (1989), 54(7), 1543-8.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16530
HMDB ID	HMDB00019
Pubchem Compound ID	49
Kegg ID	C00141
ChemSpider ID	48
Wikipedia ID	Alpha-Ketoisovaleric acid
BioCyc ID	2-KETO-ISOVALERATE
EcoCyc ID	2-KETO-ISOVALERATE
Ligand Expo	KIV

Enzymes

Protein Details

1. Dihydroxy-acid dehydratase

General function:: Involved in metabolic process
Specific function:: 2,3-dihydroxy-3-methylbutanoate = 3-methyl-2- oxobutanoate + H(2)O
Gene Name:: ilvD
Uniprot ID:: P05791
Molecular weight:: 65531

Reactions

2,3-dihydroxy-3-methylbutanoate = 3-methyl-2-oxobutanoate + H(2)O.

Protein Details

2. Valine--pyruvate aminotransferase

General function:: Involved in transferase activity
Specific function:: L-valine + pyruvate = 3-methyl-2-oxobutanoate + L-alanine
Gene Name:: avtA
Uniprot ID:: P09053
Molecular weight:: 46711

Reactions

L-valine + pyruvate = 3-methyl-2-oxobutanoate + L-alanine.

Protein Details

3. 2-isopropylmalate synthase

General function:: Involved in 2-isopropylmalate synthase activity
Specific function:: Catalyzes the condensation of the acetyl group of acetyl-CoA with 3-methyl-2-oxobutanoate (2-oxoisovalerate) to form 3-carboxy-3-hydroxy-4-methylpentanoate (2-isopropylmalate)
Gene Name:: leuA
Uniprot ID:: P09151
Molecular weight:: 57297

Reactions

Acetyl-CoA + 3-methyl-2-oxobutanoate + H(2)O = (2S)-2-isopropylmalate + CoA.

Protein Details

4. 3-methyl-2-oxobutanoate hydroxymethyltransferase

General function:: Involved in 3-methyl-2-oxobutanoate hydroxymethyltransferase activity
Specific function:: Catalyzes the reversible reaction in which hydroxymethyl group from 5,10-methylenetetrahydrofolate is tranferred onto alpha-ketoisovalerate to form ketopantoate
Gene Name:: panB
Uniprot ID:: P31057
Molecular weight:: 28237

Reactions

5,10-methylenetetrahydrofolate + 3-methyl-2-oxobutanoate + H(2)O = tetrahydrofolate + 2-dehydropantoate.

Protein Details

5. Uncharacterized aminotransferase yfbQ

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Specific function unknown
Gene Name:: yfbQ
Uniprot ID:: P0A959
Molecular weight:: 45517

Reactions

L-alanine + 2-oxoglutarate = pyruvate + L-glutamate.

Protein Details

6. Branched-chain-amino-acid aminotransferase

General function:: Involved in catalytic activity
Specific function:: Acts on leucine, isoleucine and valine
Gene Name:: ilvE
Uniprot ID:: P0AB80
Molecular weight:: 34093

Reactions

L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate.
L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate.
L-valine + 2-oxoglutarate = 3-methyl-2-oxobutanoate + L-glutamate.

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alpha-Ketoisovaleric acid (M2MDB000606)

Structure for #<Compound:0xa6e26cb4>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions