Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11) Show 11 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:21:45 UTC

Update Date

2023-02-21 17:30:00 UTC

HMDB ID

HMDB0060451

Secondary Accession Numbers

HMDB60451

Metabolite Identification

Common Name

Chloral hydrate

Description

Chloral hydrate is a sedative and hypnotic drug as well as a chemical reagent and precursor. The name chloral hydrate indicates that it is formed from chloral (trichloroacetaldehyde) by the addition of one molecule of water. Its chemical formula is C2H3Cl3O2. It was discovered through the chlorination of ethanol in 1832 by Justus von Liebig in Gießen. Its sedative properties were first published in 1869 and subsequently, because of its easy synthesis, its use was widespread. (Wikipedia )

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,1,1-Trichloro-2,2-dihydroxyethane	ChEBI
1,1,1-Trichloro-2,2-ethanediol	ChEBI
2,2,2-Trichloro-1,1-ethanediol	ChEBI
Aquachloral supprettes	ChEBI
Chloral monohydrate	ChEBI
Chloralhydrat	ChEBI
Knockout drops	ChEBI
Noctec	ChEBI
Somnote	ChEBI
Trichloracetaldehyd-hydrat	ChEBI
Trichloroacetaldehyde hydrate	ChEBI
Chloral monohydric acid	Generator
Trichloroacetaldehyde hydric acid	Generator
Chloral hydric acid	Generator
Hydrate, chloral	HMDB

Chemical Formula

C₂H₃Cl₃O₂

Average Molecular Weight

165.403

Monoisotopic Molecular Weight

163.919862461

IUPAC Name

2,2,2-trichloroethane-1,1-diol

Traditional Name

chloral hydrate

CAS Registry Number

Not Available

SMILES

OC(O)C(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H

InChI Key

RNFNDJAIBTYOQL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Halohydrins

Sub Class

Chlorohydrins

Direct Parent

Chlorohydrins

Alternative Parents

Substituents

Chlorohydrin
Carbonyl hydrate
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine compound (CHEBI:28142 )
aldehyde hydrate (CHEBI:28142 )
ethanediol (CHEBI:28142 )
a small molecule (CPD0-1476 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060451)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	43.4 g/L	ALOGPS
logP	0.88	ALOGPS
logP	0.69	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	29.25 m³·mol⁻¹	ChemAxon
Polarizability	11.88 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	126.848	30932474
DeepCCS	[M-H]-	124.309	30932474
DeepCCS	[M-2H]-	160.623	30932474
DeepCCS	[M+Na]+	135.447	30932474
AllCCS	[M+H]+	132.4	32859911
AllCCS	[M+H-H2O]+	128.5	32859911
AllCCS	[M+NH4]+	136.0	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	134.9	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	143.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.81 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4285 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1229.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	423.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	119.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	307.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	152.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	342.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	321.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	388.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	745.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	155.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1014.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	344.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	623.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	180.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chloral hydrate	OC(O)C(Cl)(Cl)Cl	2057.0	Standard polar	33892256
Chloral hydrate	OC(O)C(Cl)(Cl)Cl	712.2	Standard non polar	33892256
Chloral hydrate	OC(O)C(Cl)(Cl)Cl	1039.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chloral hydrate,1TMS,isomer #1	C[Si](C)(C)OC(O)C(Cl)(Cl)Cl	1164.6	Semi standard non polar	33892256
Chloral hydrate,2TMS,isomer #1	C[Si](C)(C)OC(O[Si](C)(C)C)C(Cl)(Cl)Cl	1277.9	Semi standard non polar	33892256
Chloral hydrate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(O)C(Cl)(Cl)Cl	1387.4	Semi standard non polar	33892256
Chloral hydrate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(O[Si](C)(C)C(C)(C)C)C(Cl)(Cl)Cl	1724.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chloral hydrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-9800000000-173349d19f15699bc4e2	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloral hydrate GC-MS (2 TMS) - 70eV, Positive	splash10-0076-9410000000-21820ed226e58fbc8ae1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloral hydrate 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 - Chloral hydrate 10V, Positive-QTOF	splash10-01ot-0900000000-c672e7ca577dd4cff3a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 20V, Positive-QTOF	splash10-03di-0900000000-66ddb4524d26c214f30a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 40V, Positive-QTOF	splash10-0002-0900000000-1f3f289553fa24dda588	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 10V, Negative-QTOF	splash10-03di-0900000000-f03879ddb1ed96167f28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 20V, Negative-QTOF	splash10-03dl-0900000000-251ef92040263c3150d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 40V, Negative-QTOF	splash10-004i-1900000000-584b46b94889a43b683f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 10V, Positive-QTOF	splash10-03di-0900000000-86a486dece507559a95d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 20V, Positive-QTOF	splash10-03di-0900000000-86a486dece507559a95d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 40V, Positive-QTOF	splash10-0159-3900000000-d50cea434c3e3f18ce68	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 10V, Negative-QTOF	splash10-03di-0900000000-56dff238afdaa1d31c63	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 20V, Negative-QTOF	splash10-03di-1900000000-81be9106d7645ecb03c5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloral hydrate 40V, Negative-QTOF	splash10-03di-5900000000-c87e1310d672bcc236e2	2021-10-12	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01563

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06899

BioCyc ID

CPD0-1476

BiGG ID

Not Available

Wikipedia Link

Chloral hydrate

METLIN ID

Not Available

PubChem Compound

2707

PDB ID

Not Available

ChEBI ID

28142

Food Biomarker Ontology

Not Available

VMH ID

M01440

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldehyde dehydrogenase, dimeric NADP-preferring

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:: ALDH3A1
Uniprot ID:: P30838
Molecular weight:: 50394.57

Reactions

Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Ion	details

Enzyme Details

2. Aldehyde dehydrogenase family 1 member A3

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:: ALDH1A3
Uniprot ID:: P47895
Molecular weight:: 56107.995

Reactions

Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Ion	details

Enzyme Details

3. Alcohol dehydrogenase 4

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH4
Uniprot ID:: P08319
Molecular weight:: 40221.335

Reactions

Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Water	details

Enzyme Details

4. Aldehyde dehydrogenase family 3 member B2

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH3B2
Uniprot ID:: P48448
Molecular weight:: 42623.62

Reactions

Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Ion	details

Enzyme Details

5. Aldehyde dehydrogenase family 3 member B1

General function:: Involved in oxidoreductase activity
Specific function:: Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:: ALDH3B1
Uniprot ID:: P43353
Molecular weight:: 51839.245

Reactions

Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Ion	details

Enzyme Details

6. Alcohol dehydrogenase class-3

General function:: Involved in zinc ion binding
Specific function:: Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:: ADH5
Uniprot ID:: P11766
Molecular weight:: 39723.945

Reactions

Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Water	details

Enzyme Details

7. Alcohol dehydrogenase 1B

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1B
Uniprot ID:: P00325
Molecular weight:: 39835.17

Reactions

Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Water	details

Enzyme Details

8. Alcohol dehydrogenase class 4 mu/sigma chain

General function:: Involved in zinc ion binding
Specific function:: Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:: ADH7
Uniprot ID:: P40394
Molecular weight:: 41480.985

Reactions

Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Water	details

Enzyme Details

9. Alcohol dehydrogenase 1A

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1A
Uniprot ID:: P07327
Molecular weight:: 39858.37

Reactions

Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Water	details

Enzyme Details

10. Alcohol dehydrogenase 6

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH6
Uniprot ID:: P28332
Molecular weight:: 39072.275

Reactions

Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Water	details

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Chloral hydrate (HMDB0060451)

MOL for HMDB0060451 (Chloral hydrate)

3D MOL for HMDB0060451 (Chloral hydrate)

3D SDF for HMDB0060451 (Chloral hydrate)

3D-SDF for HMDB0060451 (Chloral hydrate)

PDB for HMDB0060451 (Chloral hydrate)

3D PDB for HMDB0060451 (Chloral hydrate)

SMILES for HMDB0060451 (Chloral hydrate)

INCHI for HMDB0060451 (Chloral hydrate)

Structure for HMDB0060451 (Chloral hydrate)

3D Structure for HMDB0060451 (Chloral hydrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions