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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 10:04:57 UTC

Update Date

2023-02-21 17:16:52 UTC

HMDB ID

HMDB0004058

Secondary Accession Numbers

HMDB04058

Metabolite Identification

Common Name

5,6-Dihydroxyindole

Description

5,6-Dihydroxyindole, also known as aminochrome or DHI, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 5,6-Dihydroxyindole is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 5,6-dihydroxyindole participates in a number of enzymatic reactions. In particular, 5,6-dihydroxyindole can be biosynthesized from L-dopachrome through the action of the enzyme tyrosinase. In addition, 5,6-dihydroxyindole can be converted into indole-5,6-quinone; which is catalyzed by the enzyme tyrosinase. In humans, 5,6-dihydroxyindole is involved in the metabolic disorder called hawkinsinuria.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
DHI	ChEBI
Dopamine lutine	ChEBI
5,6-Dihydroxyindole	HMDB
Indole-5,6-diol	HMDB
Indolylquinol	HMDB

Chemical Formula

C₈H₇NO₂

Average Molecular Weight

149.1467

Monoisotopic Molecular Weight

149.047678473

IUPAC Name

1H-indole-5,6-diol

Traditional Name

5,6-dihydroxyindole

CAS Registry Number

3131-52-0

SMILES

OC1=C(O)C=C2C=CNC2=C1

InChI Identifier

InChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H

InChI Key

SGNZYJXNUURYCH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyindole (CHEBI:27404 )
a small molecule (DIHYDROXYINDOLE )

Ontology

Not Available

Exogenous (HMDB: HMDB0004058)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004058)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)
Tyrosine Metabolism (HMDB: HMDB0004058)
Eumelanin Biosynthesis (PathBank: SMP0121124)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (HMDB: HMDB0004058)
Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0004058)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.78 g/L	ALOGPS
logP	1.11	ALOGPS
logP	1.46	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.72	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	56.25 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.11 m³·mol⁻¹	ChemAxon
Polarizability	14.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	130.455	31661259
DarkChem	[M-H]-	129.589	31661259
DeepCCS	[M+H]+	130.347	30932474
DeepCCS	[M-H]-	127.184	30932474
DeepCCS	[M-2H]-	164.154	30932474
DeepCCS	[M+Na]+	139.522	30932474
AllCCS	[M+H]+	130.6	32859911
AllCCS	[M+H-H2O]+	125.8	32859911
AllCCS	[M+NH4]+	135.0	32859911
AllCCS	[M+Na]+	136.3	32859911
AllCCS	[M-H]-	126.5	32859911
AllCCS	[M+Na-2H]-	127.3	32859911
AllCCS	[M+HCOO]-	128.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Dihydroxyindole	OC1=C(O)C=C2C=CNC2=C1	3514.5	Standard polar	33892256
5,6-Dihydroxyindole	OC1=C(O)C=C2C=CNC2=C1	1845.1	Standard non polar	33892256
5,6-Dihydroxyindole	OC1=C(O)C=C2C=CNC2=C1	1844.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,6-Dihydroxyindole,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C[NH]2)C=C1O	1897.5	Semi standard non polar	33892256
5,6-Dihydroxyindole,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)[NH]C=C2	1909.4	Semi standard non polar	33892256
5,6-Dihydroxyindole,1TMS,isomer #3	C[Si](C)(C)N1C=CC2=CC(O)=C(O)C=C21	1954.4	Semi standard non polar	33892256
5,6-Dihydroxyindole,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C=C2	1964.9	Semi standard non polar	33892256
5,6-Dihydroxyindole,2TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=CN2[Si](C)(C)C)C=C1O	1940.9	Semi standard non polar	33892256
5,6-Dihydroxyindole,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C)C=C2	1949.6	Semi standard non polar	33892256
5,6-Dihydroxyindole,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2	2024.3	Semi standard non polar	33892256
5,6-Dihydroxyindole,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2	1977.1	Standard non polar	33892256
5,6-Dihydroxyindole,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2	1892.3	Standard polar	33892256
5,6-Dihydroxyindole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C[NH]2)C=C1O	2165.6	Semi standard non polar	33892256
5,6-Dihydroxyindole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[NH]C=C2	2173.8	Semi standard non polar	33892256
5,6-Dihydroxyindole,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=CC2=CC(O)=C(O)C=C21	2229.8	Semi standard non polar	33892256
5,6-Dihydroxyindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C=C2	2450.1	Semi standard non polar	33892256
5,6-Dihydroxyindole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CN2[Si](C)(C)C(C)(C)C)C=C1O	2443.1	Semi standard non polar	33892256
5,6-Dihydroxyindole,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C=C2	2448.0	Semi standard non polar	33892256
5,6-Dihydroxyindole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2	2679.8	Semi standard non polar	33892256
5,6-Dihydroxyindole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2	2630.4	Standard non polar	33892256
5,6-Dihydroxyindole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2	2263.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydroxyindole GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-0900000000-04c8c0b24d6ead789b88	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydroxyindole GC-MS (2 TMS) - 70eV, Positive	splash10-00di-4190000000-0de343d929acc2e0ab2f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydroxyindole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 10V, Positive-QTOF	splash10-0udi-0900000000-cd7bde656f825967dce0	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 20V, Positive-QTOF	splash10-0udi-0900000000-fc1c09de4df4722d5f82	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 40V, Positive-QTOF	splash10-00sl-4900000000-88e693a5f86ce8b2fc07	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 10V, Negative-QTOF	splash10-0002-0900000000-48fdac0fa8522c16328b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 20V, Negative-QTOF	splash10-0002-0900000000-2d3e6f8819c9c5d32c21	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 40V, Negative-QTOF	splash10-00kg-4900000000-c98c0942f4239d6904b6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 10V, Positive-QTOF	splash10-0udi-0900000000-e9c84d792f3855d1e622	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 20V, Positive-QTOF	splash10-0udi-2900000000-6476034159460897f408	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 40V, Positive-QTOF	splash10-0ufu-9300000000-b351609273dd4b0ae8d6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 10V, Negative-QTOF	splash10-0002-0900000000-d32a0a3b410ab4200586	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 20V, Negative-QTOF	splash10-0002-1900000000-7917015f2c051992bf5a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 40V, Negative-QTOF	splash10-00kf-9300000000-bade444c07fe0e0b86fe	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01811

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023293

KNApSAcK ID

Not Available

Chemspider ID

102690

KEGG Compound ID

C05578

BioCyc ID

DIHYDROXYINDOLE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7009

PubChem Compound

114683

PDB ID

Not Available

ChEBI ID

27404

Food Biomarker Ontology

Not Available

VMH ID

CE4888

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Harley-Mason, John. Melanin and its precursors. VI. Further synthesis of 5,6-dihydroxyindole and its derivatives. Journal of the Chemical Society (1953), 200-3.

Material Safety Data Sheet (MSDS)

Not Available

General References

Pavel S: A new possible pathogenesis of some gallstones. Med Hypotheses. 1984 Jul;14(3):285-92. [PubMed:6472156 ]
Pavel S, Muskiet FA: Eumelanin (precursor) metabolites as markers for pigmented malignant melanoma: a preliminary report. Cancer Detect Prev. 1983;6(1-2):311-6. [PubMed:6883388 ]
Pavel S, Boverhof R, Wolthers BG: Identification of 5-hydroxy-6-indolyl-O-sulfate in urine of patients with malignant melanoma. J Invest Dermatol. 1984 Jun;82(6):577-9. [PubMed:6547157 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Reactions

5,6-Dihydroxyindole + Oxygen → Indole-5,6-quinone + Water	details

Enzyme Details

2. L-dopachrome tautomerase

General function:: Involved in oxidoreductase activity
Specific function:: Involved in regulating eumelanin and phaeomelanin levels.
Gene Name:: DCT
Uniprot ID:: P40126
Molecular weight:: 62928.215

Enzyme Details

3. D-dopachrome decarboxylase

General function:: Involved in D-dopachrome decarboxylase activity
Specific function:: Tautomerization of D-dopachrome with decarboxylation to give 5,6-dihydroxyindole (DHI).
Gene Name:: DDT
Uniprot ID:: P30046
Molecular weight:: 12711.605

Reactions

D-Dopachrome → 5,6-Dihydroxyindole + CO(2)	details

Showing metabocard for 5,6-Dihydroxyindole (HMDB0004058)

MOL for HMDB0004058 (5,6-Dihydroxyindole)

3D MOL for HMDB0004058 (5,6-Dihydroxyindole)

3D SDF for HMDB0004058 (5,6-Dihydroxyindole)

3D-SDF for HMDB0004058 (5,6-Dihydroxyindole)

PDB for HMDB0004058 (5,6-Dihydroxyindole)

3D PDB for HMDB0004058 (5,6-Dihydroxyindole)

SMILES for HMDB0004058 (5,6-Dihydroxyindole)

INCHI for HMDB0004058 (5,6-Dihydroxyindole)

Structure for HMDB0004058 (5,6-Dihydroxyindole)

3D Structure for HMDB0004058 (5,6-Dihydroxyindole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions