MiMeDB: Showing metabocard for L-Xylulose (MMDBc0000149)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:37:39 UTC

Update Date

2024-04-30 19:31:13 UTC

Metabolite ID

MMDBc0000149

Metabolite Identification

Common Name

L-Xylulose

Description

L-Xylulose (CAS: 527-50-4), also known as L-threo-2-pentulose, is a ketopentose - a monosaccharide containing five carbon atoms, including a ketone functional group. It has the chemical formula C5H10O5. L-Xylulose accumulates in the urine of pentosuria patients. Since L-xylulose is a reducing sugar like D-glucose, pentosuria patients have been wrongly diagnosed in the past to be diabetic.

Structure

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

Synonyms

Value	Source
L-Lyxulose	HMDB
L-Threo-pentulose	HMDB
L-Threo-2-pentulose	HMDB
Xylulose	HMDB
beta-L-Threo-pentulofuranose	HMDB
beta-L-Threo-2-pentulofuranose	HMDB
Β-L-threo-pentulofuranose	HMDB
Β-L-threo-2-pentulofuranose	HMDB
L-Xylulose	HMDB

Molecular Formula

C₅H₁₀O₅

Average Mass

150.13

Monoisotopic Mass

150.052823422

IUPAC Name

(2S,3R,4S)-2-(hydroxymethyl)oxolane-2,3,4-triol

Traditional Name

(2S,3R,4S)-2-(hydroxymethyl)oxolane-2,3,4-triol

CAS Registry Number

1932596-80-9

SMILES

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

InChI Identifier

InChI=1S/C5H10O5/c6-2-5(9)4(8)3(7)1-10-5/h3-4,6-9H,1-2H2/t3-,4+,5-/m0/s1

InChI Key

LQXVFWRQNMEDEE-LMVFSUKVSA-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
Oxolane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1310 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.1	ChemAxon
logS	0.94	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	30.4 m³·mol⁻¹	ChemAxon
Polarizability	13.61 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	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-d014866a9eaa4bcc1c15	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fv-9000000000-fac868271cf0145b751c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052e-9000000000-3310acb8673d3f763bfa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052b-8900000000-6174ea340f73118a4e71	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9000000000-3155b6a3b975db3bc626	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-cc7ea805a3871cd388b5	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

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
MMDBp0191976	L-xylulose reductase	Enzyme	Q7Z4W1	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013527	L-Arabitol	Hydrogen Ion	L-arabinitol 4-dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0013606	NADP(+)	Hydrogen Ion	L-xylulose reductase	Reduction	RHEA	34755880
MMDBr0013816	Adenosine triphosphate	ADP	L-xylulose/3-keto-L-gulonate kinase	Phosphorylation	RHEA	34755880
MMDBr0013817	Adenosine triphosphate	ADP	L-xylulose/3-keto-L-gulonate kinase	Phosphorylation	RHEA	34755880
MMDBr0016646	L-Ribulose	L-Threo-2-pentulose	5-keto-L-gluconate epimerase	Epimerization	RHEA	34755880
MMDBr0017727	NAD	Hydrogen Ion	NADH-dependent L-xylulose reductase	Reduction	RHEA	34755880
MMDBr0017728	NAD	Hydrogen Ion	NADH-dependent L-xylulose reductase	Reduction	RHEA	34755880
MMDBr0017729	Hydrogen Ion	NAD	NADH-dependent L-xylulose reductase	Reduction	RHEA	34755880
MMDBr0019366	L-Lyxopyranose	L-Xylulose	L-rhamnose isomerase	Isomerization	PathBank	31602464
MMDBr0019367	L-Xylulose	Hydrogen Ion	L-xylulose/3-keto-L-gulonate kinase	Phosphorylation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Leukoencephalopathy		Association	Human Cerebrospinal Fluid (CSF)	HMDB	14988808
Ribose-5-phosphate isomerase deficiency		Association	Human Blood	HMDB	14988808

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	10	Human feces; Human saliva	Microbial culture
Bacteria	Actinobacteria	23	Human ; Human feces; Human saliva; Human pleural fluid plaque; Human dental plaque; Human sputum	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	55	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Chicken	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	94	Human stool; Human ; Human feces; Human pleural fluid plaque; Human sputum; Human saliva; Human urine; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	64	Human feces; Human stool; Human saliva; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Thermotogae	1
Bacteria/NULL	Actinobacteria	1	Human ; Human feces; Human saliva; Human pleural fluid plaque; Human dental plaque; Human sputum	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction

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
Human Cerebrospinal fluid (csf)	Detected and Quantified	254.0		88.0	166.0	uM	Adult (>18 years old)	Both	Leukoencephalopathy and peripheral neuropathy	HMDB	14988808
Human Blood	Detected and Quantified	5.0		0.0	10.0	uM	Adult (>18 years old)	Both	Ribose-5-phosphate isomerase deficiency	HMDB	14988808
Human Cerebrospinal fluid (csf)	Detected and Quantified	< 5.0				uM	Children (1-13 years old)	Both	Normal	HMDB	14988808
Human Urine	Detected and Quantified			0.0	0.5	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	14988808
Human Blood	Detected and Quantified	9.0	12.0			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000751

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Xylulose

METLIN ID

Not Available

PubChem Compound

89810215

PDB ID

Not Available

ChEBI ID

17399

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Oka H, Suzuki S, Suzuki H, Oda T: Increased urinary excretion of L-xylulose in patients with liver cirrhosis. Clin Chim Acta. 1976 Mar 1;67(2):131-6. doi: 10.1016/0009-8981(76)90251-5. [PubMed:1248150 ]

Showing metabocard for L-Xylulose (MMDBc0000149)

MOL for #<Metabolite:0x00007fa5084ef6d8>

3D MOL for #<Metabolite:0x00007fa5084ef6d8>

3D SDF for #<Metabolite:0x00007fa5084ef6d8>

3D-SDF for #<Metabolite:0x00007fa5084ef6d8>

PDB for #<Metabolite:0x00007fa5084ef6d8>

3D PDB for #<Metabolite:0x00007fa5084ef6d8>

SMILES for #<Metabolite:0x00007fa5084ef6d8>

INCHI for #<Metabolite:0x00007fa5084ef6d8>

Structure for #<Metabolite:0x00007fa5084ef6d8>

3D Structure for #<Metabolite:0x00007fa5084ef6d8>