MiMeDB: Showing metabocard for 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one (MMDBc0054135)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:54:43 UTC

Update Date

2022-09-01 02:27:29 UTC

Metabolite ID

MMDBc0054135

Metabolite Identification

Common Name

1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one

Description

1,2-Dihydroxy-3-keto-5-methylthiopentene, also known as 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one, belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom. 1,2-Dihydroxy-3-keto-5-methylthiopentene exists in all living species, ranging from bacteria to plants to humans. 1,2-Dihydroxy-3-keto-5-methylthiopentene has been detected, but not quantified in, several different foods, such as oats (Avena sativa), endives (Cichorium endivia), lambsquarters (Chenopodium album), capers (Capparis spinosa), and babassu palms (Attalea speciosa). This could make 1,2-dihydroxy-3-keto-5-methylthiopentene a potential biomarker for the consumption of these foods. 1,2-Dihydroxy-3-keto-5-methylthiopentene is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on 1,2-Dihydroxy-3-keto-5-methylthiopentene.

Structure

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

Synonyms

Value	Source
1,2-Dihydroxy-5-(methylsulfanyl)pent-1-en-3-one	ChEBI
1,2-Dihydroxy-5-(methylsulphanyl)pent-1-en-3-one	Generator
Acireductone	ChEBI, HMDB
1,2-Dihydroxy-3-keto-5-methylthiopentane	HMDB
1,2-Dihydroxy-3-keto-5-methylthiopentene anion	HMDB
1,2-Dihydroxy-5-(methylthio)pent-1-en-3-one	HMDB

Molecular Formula

C₆H₁₀O₃S

Average Mass

162.207

Monoisotopic Mass

162.035064876

IUPAC Name

(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one

Traditional Name

(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one

CAS Registry Number

Not Available

SMILES

CSCCC(=O)C(\O)=C\O

InChI Identifier

InChI=1S/C6H10O3S/c1-10-3-2-5(8)6(9)4-7/h4,7,9H,2-3H2,1H3/b6-4-

InChI Key

CILXJJLQPTUUSS-XQRVVYSFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-branched alpha,beta-unsaturated ketones

Alternative Parents

Substituents

Alpha-branched alpha,beta-unsaturated-ketone
Vinylogous acid
Enone
Alpha-hydroxy ketone
Acryloyl-group
Ketone
Enediol
Dialkylthioether
Sulfenyl compound
Thioether
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aliphatic sulfide (CHEBI:49252 )
enone (CHEBI:49252 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	8.75 g/L	ALOGPS
logP	0.07	ALOGPS
logP	0.81	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.87 m³·mol⁻¹	ChemAxon
Polarizability	16.29 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-9300000000-19a09fc38a4607410081	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-025c-9170000000-6b6fd50d76488524c888	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1900000000-523c47d24f3c45c4f285	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-07xs-9700000000-cbbc0baabd68adaf65ad	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-c591ef1f6d20bddce525	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9300000000-bd31c9d726fbcfa6d7e1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9100000000-4d0c04f4b382ef0d5b9c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-96c889c8c6acb6410bf6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ik9-7900000000-4e7dffabd3e521b59a33	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bta-9000000000-4dee6c63f979437272b0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dj-9000000000-e4050047631669464d94	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9100000000-6f5f734e698f1dbf5d5c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0195483	Enolase-phosphatase E1	Unknown	Q9UHY7	Homo sapiens
MMDBp0196264	1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase	Enzyme	Q9BV57	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013286	1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one	3-Methylthiopropionic acid	Acireductone dioxygenase	Oxygenation	RHEA	34755880
MMDBr0013319	2-hydroxy-5-methylsulfanyl-3-oxopent-1-enyl phosphate	1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one	Bifunctional enzyme MtnB/MtnX	Dephosphorylation	RHEA	34755880
MMDBr0014134	5-(methylsulfanyl)-2,3-dioxopentyl phosphate	1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one	Enolase-phosphatase E1	Enolization	RHEA	34755880
MMDBr0014459	1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one	4-methylsulfanyl-2-oxobutanoic acid	Acireductone dioxygenase	Oxygenation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	80	Human ; Human feces; Human subgingival plaque
Eukaryota/Fungi	Ascomycota	41
Bacteria	Aquificae	4
Bacteria	Firmicutes	26	Human ; Human feces
Eukaryota/Fungi	Basidiomycota	11	Human feces
Bacteria	Actinobacteria	4	Human
Bacteria	Spirochaetes	6	Human
Bacteria	Cyanobacteria	16	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0012134

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028796

KNApSAcK ID

Not Available

Chemspider ID

4575316

KEGG Compound ID

C15606

BioCyc ID

CPD-85

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5462190

PDB ID

Not Available

ChEBI ID

49252

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one (MMDBc0054135)

MOL for #<Metabolite:0x00007f5a880194f8>

3D MOL for #<Metabolite:0x00007f5a880194f8>

3D SDF for #<Metabolite:0x00007f5a880194f8>

3D-SDF for #<Metabolite:0x00007f5a880194f8>

PDB for #<Metabolite:0x00007f5a880194f8>

3D PDB for #<Metabolite:0x00007f5a880194f8>

SMILES for #<Metabolite:0x00007f5a880194f8>

INCHI for #<Metabolite:0x00007f5a880194f8>

Structure for #<Metabolite:0x00007f5a880194f8>

3D Structure for #<Metabolite:0x00007f5a880194f8>