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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

enzymes (6) Show 6 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:45:29 UTC

HMDB ID

HMDB0001301

Secondary Accession Numbers

HMDB0002240
HMDB01301
HMDB02240

Metabolite Identification

Common Name

1-Pyrroline-5-carboxylic acid

Description

1-Pyrroline-5-carboxylic acid (CAS: 2906-39-0) is an enamine or an imino acid that forms upon the spontaneous dehydration of L-glutamate gamma-semialdehyde in aqueous solutions. The stereoisomer (S)-1-pyrroline-5-carboxylate is an intermediate in glutamate metabolism, arginine degradation, and proline biosynthesis and degradation. It can also be converted into or be formed from three amino acids: L-glutamate, L-ornithine, and L-proline. In particular, it is synthesized via the oxidation of proline by pyrroline-5-carboxylate reductase 1 (PYCR1) (EC 1.5.1.2) or by proline dehydrogenase (PRODH) (EC 1.5.99.8). It is hydrolyzed into L-glutamate by delta-1-pyrroline-5-carboxylate dehydrogenase (ALDH4A1) (EC 1.5.1.12). It is also one of the few metabolites that can act as a precursor to other metabolites of both the urea cycle and the tricarboxylic acid (TCA) cycle. Under certain conditions, pyrroline-5-carboxylate can act as a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of pyrroline-5-carboxylate are associated with at least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency. Hyperprolinemia type II results in high levels of pyrroline-5-carboxylate. People with hyperprolinemia type II have signs and symptoms that vary in severity, but they are more likely than type I to have seizures or intellectual disability. Pyrroline-5-carboxylate is highly reactive and excess quantities have been shown to cause cell death and apoptosis (PMID: 15548746 ).

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-Pyrroline-5-carboxylate	ChEBI, KEGG
L-1-Pyrroline-5-carboxylate	ChEBI, KEGG
1-Pyrroline-5-carboxylic acid	Generator
(S)-1-Pyrroline-5-carboxylic acid	Generator
L-1-Pyrroline-5-carboxylic acid	Generator
delta-1-Pyrroline-5-carboxylate	MeSH
delta-1-Pyrroline-5-carboxylate, (+-)-isomer	MeSH
delta-1-Pyrroline-5-carboxylic acid	MeSH
delta-1-Pyrroline-5-carboxylate, 14C-labeled, (+-)-isomer	MeSH
delta(1)Pyrroline-5-carboxylate	MeSH
Pyrroline-5-carboxylate	MeSH
(2S)-3,4-Dihydro-2H-pyrrole-2-carboxylic acid	HMDB
(S)-1-Pyrroline-5-carboxylate	HMDB
3,4-Dihydro-2H-pyrrole-2-carboxylic acid	HMDB
delta1-Pyrroline-5-carboxylic acid	HMDB
Δ1-Pyrroline-5-carboxylic acid	HMDB

Chemical Formula

C₅H₇NO₂

Average Molecular Weight

113.1146

Monoisotopic Molecular Weight

113.047678473

IUPAC Name

(2S)-3,4-dihydro-2H-pyrrole-2-carboxylic acid

Traditional Name

L-1-pyrroline-5-carboxylate

CAS Registry Number

64199-88-8

SMILES

OC(=O)[C@@H]1CCC=N1

InChI Identifier

InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)/t4-/m0/s1

InChI Key

DWAKNKKXGALPNW-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Pyrroline
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Carbonyl group
Imine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

1-pyrroline-5-carboxylic acid (CHEBI:371 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Nontypified gene mutations

Organic acidemia

Succinic semialdehyde dehydrogenase deficiency (PMID: 11978597 , PMID: 12127325 , PMID: 12127325 , +1

Source	Link
Pubmed	PMID: 11978597
Pubmed	PMID: 12127325
Pubmed	PMID: 12127325
Pubmed	PMID: 8087979

)

Disposition

Biological location

Excreta

Feces

Organ

Intestine

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Herbal teas

Taco shell
Tostada shell

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Soy

Soy products

Soy bean

Baking goods

Wrappers

Wonton wrapper

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

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	13.1 g/L	ALOGPS
logP	-0.01	ALOGPS
logP	-2.3	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	6.07	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.4 m³·mol⁻¹	ChemAxon
Polarizability	10.72 Å³	ChemAxon
Number of Rings	1	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]+	119.171	30932474
DeepCCS	[M-H]-	115.484	30932474
DeepCCS	[M-2H]-	152.819	30932474
DeepCCS	[M+Na]+	127.819	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Pyrroline-5-carboxylic acid	OC(=O)[C@@H]1CCC=N1	1722.0	Standard polar	33892256
1-Pyrroline-5-carboxylic acid	OC(=O)[C@@H]1CCC=N1	1045.2	Standard non polar	33892256
1-Pyrroline-5-carboxylic acid	OC(=O)[C@@H]1CCC=N1	1076.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Pyrroline-5-carboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCC=N1	1116.5	Semi standard non polar	33892256
1-Pyrroline-5-carboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCC=N1	1365.1	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 - 1-Pyrroline-5-carboxylic acid 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 - 1-Pyrroline-5-carboxylic acid 10V, Positive-QTOF	splash10-03dj-9700000000-f2bc2275638f96dc74ac	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 20V, Positive-QTOF	splash10-014i-9100000000-72dff6639c24448bec9c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 40V, Positive-QTOF	splash10-014l-9000000000-28eb1358005b28459deb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 10V, Negative-QTOF	splash10-03di-5900000000-0720aa91caee03b9364e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 20V, Negative-QTOF	splash10-02t9-9400000000-cfcc87863f675fb12691	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 40V, Negative-QTOF	splash10-00kf-9000000000-a15b91c200295166bf9e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 10V, Positive-QTOF	splash10-014i-9000000000-e0673bc7e6a6226fb72e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 20V, Positive-QTOF	splash10-014i-9000000000-e0673bc7e6a6226fb72e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 40V, Positive-QTOF	splash10-014i-9000000000-4f0cf32a2f9df52b4ad3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 10V, Negative-QTOF	splash10-03di-2900000000-043a05a728838fd3b2fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 20V, Negative-QTOF	splash10-014i-9200000000-91f194ef0ca23d3de318	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-5-carboxylic acid 40V, Negative-QTOF	splash10-00kf-9000000000-f29d6251972eea5ba613	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Intestine

Pathways

Name	SMPDB/PathBank	KEGG
Glutamate Metabolism
Arginine and proline metabolism	Not Available
Prolidase Deficiency (PD)		Not Available
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)		Not Available
Hyperprolinemia Type II		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

L-DELTA1-PYRROLINE_5-CARBOXYLATE

BiGG ID

Not Available

Wikipedia Link

1-Pyrroline-5-carboxylic acid

METLIN ID

Not Available

PubChem Compound

440162

PDB ID

Not Available

ChEBI ID

371

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Vogel, Henry J.; Davis, Bernard D. Glutamic g-semialdehyde and D1-pyrroline-5-carboxylic acid, intermediates in the biosynthesis of proline. Journal of the American Chemical Society (1952), 74 109-12.

Material Safety Data Sheet (MSDS)

Not Available

General References

Simila S: Hydroxyproline metabolism in type II hyperprolinaemia. Ann Clin Biochem. 1979 Jul;16(4):177-81. [PubMed:533224 ]
Humbertclaude V, Rivier F, Roubertie A, Echenne B, Bellet H, Vallat C, Morin D: Is hyperprolinemia type I actually a benign trait? Report of a case with severe neurologic involvement and vigabatrin intolerance. J Child Neurol. 2001 Aug;16(8):622-3. [PubMed:11510941 ]
Mixson AJ, Phang JM: The uptake of pyrroline 5-carboxylate. Group translocation mediating the transfer of reducing-oxidizing potential. J Biol Chem. 1988 Aug 5;263(22):10720-4. [PubMed:3392037 ]
Wakabayashi Y: Tissue-selective expression of enzymes of arginine synthesis. Curr Opin Clin Nutr Metab Care. 1998 Jul;1(4):335-9. [PubMed:10565370 ]
Onenli-Mungan N, Yuksel B, Elkay M, Topaloglu AK, Baykal T, Ozer G: Type II hyperprolinemia: a case report. Turk J Pediatr. 2004 Apr-Jun;46(2):167-9. [PubMed:15214748 ]
Fleming GA, Hagedorn CH, Granger AS, Phang JM: Pyrroline-5-carboxylate in human plasma. Metabolism. 1984 Aug;33(8):739-42. [PubMed:6748947 ]
Deuschle K, Funck D, Forlani G, Stransky H, Biehl A, Leister D, van der Graaff E, Kunze R, Frommer WB: The role of [Delta]1-pyrroline-5-carboxylate dehydrogenase in proline degradation. Plant Cell. 2004 Dec;16(12):3413-25. doi: 10.1105/tpc.104.023622. Epub 2004 Nov 17. [PubMed:15548746 ]

Enzymes

Enzyme Details

1. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes.
Gene Name:: ALDH4A1
Uniprot ID:: P30038
Molecular weight:: 55117.24

Reactions

1-Pyrroline-5-carboxylic acid + NAD(P)(+) + Water → L-Glutamic acid + NAD(P)H	details
1-Pyrroline-5-carboxylic acid + NAD + Water → L-Glutamic acid + NADH + Hydrogen Ion	details
1-Pyrroline-5-carboxylic acid + NADP + Water → L-Glutamic acid + NADPH + Hydrogen Ion	details

Enzyme Details

2. Pyrroline-5-carboxylate reductase 1, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Housekeeping enzyme that catalyzes the last step in proline biosynthesis. Can utilize both NAD and NADP, but has higher affinity for NAD. Involved in the cellular response to oxidative stress.
Gene Name:: PYCR1
Uniprot ID:: P32322
Molecular weight:: 33360.27

Reactions

L-Proline + NAD(P)(+) → 1-Pyrroline-5-carboxylic acid + NAD(P)H	details
L-Proline + NAD → 1-Pyrroline-5-carboxylic acid + NADH + Hydrogen Ion	details
L-Proline + NADP → 1-Pyrroline-5-carboxylic acid + NADPH + Hydrogen Ion	details

Enzyme Details

3. Pyrroline-5-carboxylate reductase 2

General function:: Involved in oxidoreductase activity
Specific function:: Housekeeping enzyme that catalyzes the last step in proline biosynthesis. In some cell types, such as erythrocytes, its primary function may be the generation of NADP(+). Can utilize both NAD and NADP. Has higher affinity for NADP, but higher catalytic efficiency with NADH.
Gene Name:: PYCR2
Uniprot ID:: Q96C36
Molecular weight:: 25867.975

Reactions

L-Proline + NAD(P)(+) → 1-Pyrroline-5-carboxylic acid + NAD(P)H	details
L-Proline + NAD → 1-Pyrroline-5-carboxylic acid + NADH + Hydrogen Ion	details
L-Proline + NADP → 1-Pyrroline-5-carboxylic acid + NADPH + Hydrogen Ion	details

Enzyme Details

4. Proline dehydrogenase 1, mitochondrial

General function:: Involved in proline dehydrogenase activity
Specific function:: Converts proline to delta-1-pyrroline-5-carboxylate.
Gene Name:: PRODH
Uniprot ID:: O43272
Molecular weight:: 56196.675

Reactions

L-Proline + acceptor → 1-Pyrroline-5-carboxylic acid + reduced acceptor	details
L-Proline + Acceptor → 1-Pyrroline-5-carboxylic acid + Reduced acceptor	details

Enzyme Details

5. Pyrroline-5-carboxylate reductase 3

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: PYCRL
Uniprot ID:: Q53H96
Molecular weight:: 29892.415

Reactions

L-Proline + NAD(P)(+) → 1-Pyrroline-5-carboxylic acid + NAD(P)H	details
L-Proline + NAD → 1-Pyrroline-5-carboxylic acid + NADH + Hydrogen Ion	details
L-Proline + NADP → 1-Pyrroline-5-carboxylic acid + NADPH + Hydrogen Ion	details

Enzyme Details

6. Probable proline dehydrogenase 2

General function:: Involved in proline dehydrogenase activity
Specific function:: Converts proline to delta-1-pyrroline-5-carboxylate (Probable).
Gene Name:: PRODH2
Uniprot ID:: Q9UF12
Molecular weight:: 58870.115

Reactions

L-Proline + acceptor → 1-Pyrroline-5-carboxylic acid + reduced acceptor	details

Showing metabocard for 1-Pyrroline-5-carboxylic acid (HMDB0001301)

MOL for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

3D MOL for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

3D SDF for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

3D-SDF for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

PDB for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

3D PDB for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

SMILES for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

INCHI for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

Structure for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

3D Structure for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions