MiMeDB: Showing metabocard for L-xylono-1,4-lactone (MMDBc0033165)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:37:20 UTC

Update Date

2025-10-07 16:07:56 UTC

Metabolite ID

MMDBc0033165

Metabolite Identification

Common Name

L-xylono-1,4-lactone

Description

L-xylono-1,4-lactone is a member of the lactone chemical class, specifically a sugar lactone that plays a role in various metabolic pathways. Its chemical structure features a cyclic ester formed from L-xylonic acid, which contributes to its reactivity and interactions in biochemical processes. L-xylono-1,4-lactone has been identified as a substrate for enzymes within the amidohydrolase superfamily, such as BmulJ_04915 from Burkholderia multivorans, which hydrolyzes a range of sugar lactones, including L-xylono-1,4-lactone itself (PMID:23214453 ). Additionally, it has been noted that L-xylono-1,4-lactone, along with other lactones like L-galactono-1,4-lactone and L-gulono-1,4-lactone, can serve as substrates in enzymatic reactions (PMID:7957197 ). This suggests that L-xylono-1,4-lactone may participate in metabolic pathways involving sugar alcohols and their derivatives, highlighting its potential role in carbohydrate metabolism.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₅H₈O₅

Average Mass

148.114

Monoisotopic Mass

148.037173366

IUPAC Name

(3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one

Traditional Name

L-xylono-1,4-lactone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3+,4-/m0/s1

InChI Key

CUOKHACJLGPRHD-NUNKFHFFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentoses

Alternative Parents

Substituents

Pentose monosaccharide
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

xylonolactone (CHEBI:18118 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	847 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.1	ChemAxon
logS	0.76	ALOGPS
pKa (Strongest Acidic)	11.63	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.82 m³·mol⁻¹	ChemAxon
Polarizability	12.78 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9200000000-57923aebd9b821766513	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-2900000000-d76c6c2ab2d323f65be1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-2900000000-ef1350e75a002dfbd727	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052p-9100000000-d00950097b42e8ee674e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-e97c530b9495b6c0d26a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-2900000000-bbbd4b6af81d996ce75d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-ca903cf3d2c2e5bee97d	2016-09-12	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	374.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	214.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	55.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	266.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (void)	2025-10-24	284.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	359.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	802.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	673.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	965.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	190.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	284.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	210.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	42.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	355.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	721.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	82.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	268.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	904.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	634.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	L-xylono-1,4-lactone_TMS_1	C[Si](C)(C)OC[C@@H]1OC(=O)[C@@H](O)[C@@H]1O	standard non polar	2025-10-24	1675.73
Gas Chromatography	L-xylono-1,4-lactone_TMS_2	C[Si](C)(C)O[C@@H]1C(=O)O[C@@H](CO)[C@H]1O	standard non polar	2025-10-24	1511.81
Gas Chromatography	L-xylono-1,4-lactone_TMS_3	C[Si](C)(C)O[C@@H]1[C@H](CO)OC(=O)[C@H]1O	standard non polar	2025-10-24	2152.7
Gas Chromatography	L-xylono-1,4-lactone_TMS_4	C[Si](C)(C)OC[C@@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-24	1869.85
Gas Chromatography	L-xylono-1,4-lactone_TMS_5	C[Si](C)(C)OC[C@@H]1OC(=O)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1560.01
Gas Chromatography	L-xylono-1,4-lactone_TMS_6	C[Si](C)(C)O[C@@H]1C(=O)O[C@@H](CO)[C@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1606.16
Gas Chromatography	L-xylono-1,4-lactone_TMS_7	C[Si](C)(C)OC[C@@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1709.09
Gas Chromatography	L-xylono-1,4-lactone_TMS_1	C[Si](C)(C)OC[C@@H]1OC(=O)[C@@H](O)[C@@H]1O	standard polar	2025-10-24	2512.4
Gas Chromatography	L-xylono-1,4-lactone_TMS_2	C[Si](C)(C)O[C@@H]1C(=O)O[C@@H](CO)[C@H]1O	standard polar	2025-10-24	2233.25
Gas Chromatography	L-xylono-1,4-lactone_TMS_3	C[Si](C)(C)O[C@@H]1[C@H](CO)OC(=O)[C@H]1O	standard polar	2025-10-24	2037.33
Gas Chromatography	L-xylono-1,4-lactone_TMS_4	C[Si](C)(C)OC[C@@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-24	1708.75
Gas Chromatography	L-xylono-1,4-lactone_TMS_5	C[Si](C)(C)OC[C@@H]1OC(=O)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	2369.53
Gas Chromatography	L-xylono-1,4-lactone_TMS_6	C[Si](C)(C)O[C@@H]1C(=O)O[C@@H](CO)[C@H]1O[Si](C)(C)C	standard polar	2025-10-24	2408.62
Gas Chromatography	L-xylono-1,4-lactone_TMS_7	C[Si](C)(C)OC[C@@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	1929.48

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02994

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18118

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 L-xylono-1,4-lactone (MMDBc0033165)

MOL for #<Metabolite:0x00007f9ad8b527f8>

3D MOL for #<Metabolite:0x00007f9ad8b527f8>

3D SDF for #<Metabolite:0x00007f9ad8b527f8>

3D-SDF for #<Metabolite:0x00007f9ad8b527f8>

PDB for #<Metabolite:0x00007f9ad8b527f8>

3D PDB for #<Metabolite:0x00007f9ad8b527f8>

SMILES for #<Metabolite:0x00007f9ad8b527f8>

INCHI for #<Metabolite:0x00007f9ad8b527f8>

Structure for #<Metabolite:0x00007f9ad8b527f8>

3D Structure for #<Metabolite:0x00007f9ad8b527f8>