ECMDB: Isocitric acid (ECMDB04088) (M2MDB000604)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)XML

Proteins (1149)

Record Information

Version

2.0

Creation Date

2012-05-31 14:04:40 -0600

Update Date

2015-09-13 12:56:13 -0600

Secondary Accession Numbers

ECMDB04088

Identification

Name:

Isocitric acid

Description

Isocitric acid is a protonated form of isocitrate, which is a substrate of the citric acid cycle. Isocitrate is formed from citrate with the help of the enzyme aconitase, and is acted upon by isocitrate dehydrogenase. Salts and esters of isocitric acid are known as isocitrates. (Wikipedia)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate
(1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate
(1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylic acid
1-Hydroxy-1,2,3-propanetricarboxylate
1-Hydroxy-1,2,3-propanetricarboxylic acid
1-Hydroxypropane-1,2,3-tricarboxylate
1-Hydroxypropane-1,2,3-tricarboxylic acid
1-Hydroxytricarballylate
1-Hydroxytricarballylic acid
3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate
3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid
3-Carboxy-2,3-dideoxy-Pentarate
3-Carboxy-2,3-dideoxy-Pentaric acid
D-threo-isocitric acid
D-Isocitrate
D-Isocitric acid
D-Threo-isocitrate
D-Threo-isocitric acid
I-CIT
Isocitrate
Isocitric acid
Threo-D(S)-iso-citrate
Threo-D(S)-iso-citric acid
Threo-D_s-isocitrate
Threo-Ds-isocitrate
Threo-Ds-isocitric acid

Chemical Formula:

C₆H₈O₇

Weight:

Average: 192.1235
Monoisotopic: 192.02700261

InChI Key:

ODBLHEXUDAPZAU-UHFFFAOYSA-N

InChI:

InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)

CAS number:

320-77-4

IUPAC Name:

1-hydroxypropane-1,2,3-tricarboxylic acid

Traditional IUPAC Name:

isocitric acid

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Beta-hydroxy acid
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tricarboxylic acid (CHEBI:30887 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

162-165 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	466 mg/mL [HMP experimental]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	52.5 g/L	ALOGPS
logP	-0.35	ALOGPS
logP	-1.4	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	3.07	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.72 m³·mol⁻¹	ChemAxon
Polarizability	15.55 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:

cis-Aconitic acid + Water <> Isocitric acid
Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH
Isocitric acid <> Glyoxylic acid + Succinic acid
Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion
Citric acid <> Isocitric acid
Isocitric acid + NADP <> Oxalosuccinic acid + NADPH + Hydrogen ion
Isocitric acid <> cis-Aconitic acid + Water
Isocitric acid + NADP > NADPH + Oxoglutaric acid + Carbon dioxide
Isocitric acid + NADP > Oxalosuccinic acid + NADPH + Hydrogen ion
Isocitric acid > Succinic acid + Glyoxylic acid
Citric acid > Isocitric acid
Citric acid + cis-Aconitic acid + Water <> Isocitric acid
Isocitric acid + NADP + Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion
Isocitric acid + NAD + Isocitric acid > Oxoglutaric acid + Carbon dioxide + NADH + Hydrogen ion
cis-Aconitic acid + Water <> Isocitric acid + Isocitric acid
Isocitric acid + Isocitric acid <> Succinic acid + Glyoxylic acid
cis-Aconitic acid + Water <> Isocitric acid
Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH
Isocitric acid <> Glyoxylic acid + Succinic acid
Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH
Isocitric acid <> Glyoxylic acid + Succinic acid

SMPDB Pathways:

Glutathione metabolism	PW000833
Secondary Metabolites: Glyoxylate cycle	PW000967
glycolate and glyoxylate degradation II	PW002021

KEGG Pathways:

Citrate cycle (TCA cycle) ec00020
Glutathione metabolism ec00480
Glyoxylate and dicarboxylate metabolism ec00630
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Reductive carboxylate cycle (CO2 fixation) ec00720

EcoCyc Pathways:

TCA cycle I (prokaryotic) TCA
glyoxylate cycle GLYOXYLATE-BYPASS
mixed acid fermentation FERMENTATION-PWY
respiration (anaerobic) ANARESP1-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) (4 TMS)	splash10-0002-1952000000-7c34751686a6bdb54cab	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0002-0963000000-459b45ff9246b5f55914	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0942000000-61204d02a28e43d21607	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00di-9420000000-4e1a59fe735855d52ce2	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-00ea-3793000000-84858fa896697420275f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1952000000-7c34751686a6bdb54cab	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0963000000-459b45ff9246b5f55914	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9420000000-4e1a59fe735855d52ce2	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00ea-3793000000-84858fa896697420275f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ba-7900000000-96194d87d52b155cf1b9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-02vi-7029500000-2bb65fc897e48cc21750	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 (TMS_1_1) - 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 (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0901310000-883764bf7b686ca7fd17	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0900000000-66d03405eeb126c6ad9d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-cdad17a11f419421c787	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0009000000-d3440c84a488b3e22212	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-3aa263561a7a49df7d3d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-1900000000-3636f87026e4206a1638	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-01w3-9600000000-ab1a2b9a29528a623d0b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0079-9000000000-3c33cefeb87f85efd5de	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-059m-9000000000-34775db8bbc008018633	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-3aa263561a7a49df7d3d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-3636f87026e4206a1638	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01w3-9600000000-ab1a2b9a29528a623d0b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0079-9000000000-3c33cefeb87f85efd5de	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-059m-9000000000-34775db8bbc008018633	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-66d03405eeb126c6ad9d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0900000000-cdad17a11f419421c787	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-03k9-2900000000-e5336d859bf90bcd904c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-2900000000-8ef1bf8afd67194ddf65	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-059f-9000000000-37227e36af9ba4db4a7e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-022i-9500000000-cb0234d7a355d54f1755	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-3900000000-1b8cb16b24c65e87915b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03ki-9500000000-d264dd60719df8b72ef3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-bf62fc70edcee073c517	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-02mi-9200000000-42ca838ca7f08cc3882e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-1900000000-8e1185b0504ea1547715	View in MoNA
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

References

References:

Ebeling K, Ruckhaberle KE, Bilek K: [Studies on the recording of cytostatic effects on organ cultures of squamous cell carcinoma of the uterine cervix] Zentralbl Gynakol. 1977;99(20):1249-59. Pubmed: 595962
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
Hennequin C, Lalanne V, Daudon M, Lacour B, Drueke T: A new approach to studying inhibitors of calcium oxalate crystal growth. Urol Res. 1993 Mar;21(2):101-8. Pubmed: 8389069
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
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
Kavanagh JP: Isocitric and citric acid in human prostatic and seminal fluid: implications for prostatic metabolism and secretion. Prostate. 1994;24(3):139-42. Pubmed: 8115279
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
Mikosha AS, Monissarenko VP, Bychkovskaia LA: [Properties of adrenocortical isocitrate dehydrogenase] Vopr Med Khim. 1981 Nov-Dec;27(6):736-9. Pubmed: 7336646
Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6. Pubmed: 813176
Sutor DJ, Percival JM, Doonan S: Isolation and identification of some urinary inhibitors of calcium phosphate formation. Clin Chim Acta. 1978 Oct 16;89(2):273-8. Pubmed: 213213
Sutor DJ, Percival JM, Doonan S: Urinary inhibitor of the formation of calcium oxalate. Br J Urol. 1979 Aug;51(4):253-5. Pubmed: 223711
Sutor DJ, Percival JM: The estimation of D-isocitric acid in urine using isocitrate dehydrogenase. Clin Chim Acta. 1978 Jun;86(2):223-5. Pubmed: 657545
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
Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
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
Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834

Synthesis Reference:

Finogenova, T. V.; Kamzolova, S. V.; Dedyukhina, E. G.; Shishkanova, N. V.; Il'chenko, A. P.; Morgunov, I. G.; Chernyavskaya, O. G.; Sokolov, A. P. Biosynthesis of citric and isocitric acids from ethanol by mutant Yarrowia lipolytica N 1 under continuous

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CHEBI ID	16087
HMDB ID	HMDB00193
Pubchem Compound ID	1198
Kegg ID	C00311
ChemSpider ID	1161
Wikipedia	Isocitric acid
BioCyc ID	THREO-DS-ISO-CITRATE
EcoCyc ID	THREO-DS-ISO-CITRATE

Enzymes

Protein Details

1. Isocitrate dehydrogenase [NADP]

General function:: Involved in magnesium ion binding
Specific function:: Isocitrate + NADP(+) = 2-oxoglutarate + CO(2) + NADPH
Gene Name:: icd
Uniprot ID:: P08200
Molecular weight:: 45756

Reactions

Isocitrate + NADP(+) = 2-oxoglutarate + CO(2) + NADPH.

Protein Details

2. Isocitrate lyase

General function:: Involved in isocitrate lyase activity
Specific function:: Catalyzes the formation of succinate and glyoxylate from isocitrate, a key step of the glyoxylate cycle. May be involved in the assimilation of one-carbon compounds via the isocitrate lyase- positive serine pathway
Gene Name:: aceA
Uniprot ID:: P0A9G6
Molecular weight:: 47521

Reactions

Isocitrate = succinate + glyoxylate.

Protein Details

3. Aconitate hydratase 1

General function:: Involved in metabolic process
Specific function:: May have an iron-responsive regulatory function
Gene Name:: acnA
Uniprot ID:: P25516
Molecular weight:: 97676

Reactions

Citrate = isocitrate.

Protein Details

4. Aconitate hydratase 2

General function:: Involved in metabolic process
Specific function:: Citrate = isocitrate
Gene Name:: acnB
Uniprot ID:: P36683
Molecular weight:: 93497

Reactions

Citrate = isocitrate.
(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate = (Z)-but-2-ene-1,2,3-tricarboxylate + H(2)O.

Protein Details

5. Uncharacterized protein ybhJ

General function:: Involved in metabolic process
Specific function:: Unknown Function
Gene Name:: ybhJ
Uniprot ID:: P75764
Molecular weight:: 81504

Isocitric acid (ECMDB04088) (M2MDB000604)

Structure for #<Compound:0xac4fa658>

Enzymes

Reactions

Reactions

Reactions

Reactions