Showing Compound D-Xylulose (FDB022698)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:08 UTC

Update date

2019-11-26 03:21:05 UTC

Primary ID

FDB022698

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-Xylulose

Description

D-xylulose is a monosaccharide containing five carbon atoms. D-xylulose is converted from xylitol by the enzyme NAD+-linked xylitol dehydrogenase (EC 1.1.1.9) in the glucuronate pathway, the most important xylitol-handling metabolic pathway in mammals. This activity has been described in human erythrocytes. Most likely, D-xylulose (as well as D-arabinose or D-ribulose) is a precursor of the pentiol D-arabitol, since pentitols are derived from their corresponding pentose phosphate precursors via pentoses. This pathway can play a role in inherited metabolic disorders underlying the accumulation of pentitols e.g., ribose 5-phosphate isomerase deficiency and transaldolase deficiency. Although pentitols are present in all living organisms, knowledge concerning their metabolism is limited. (PMID: 15234337, Mol Genet Metabolite 2004 Jul;82(3):231-7.) [HMDB]. D-Xylulose is found in many foods, some of which are garden onion, american cranberry, cucumber, and radish.

CAS Number

551-84-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
D-Lyxulose	ChEBI
D-Threo-pentulose	ChEBI
D-Xul	ChEBI
Lyxulose	MeSH
Xylulose, (D-threo)-isomer	MeSH
Xylulose	MeSH
Xylulose, (L-threo)-isomer	MeSH
D-threo-Pentulose	hmdb
D-Xylulose	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	678 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.6	ChemAxon
logS	0.65	ALOGPS
pKa (Strongest Acidic)	10.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.6 m³·mol⁻¹	ChemAxon
Polarizability	13.53 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

Chemical Formula

C5H10O5

IUPAC name

(3S,4R)-1,3,4,5-tetrahydroxypentan-2-one

InChI Identifier

InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1

InChI Key

ZAQJHHRNXZUBTE-WUJLRWPWSA-N

Isomeric SMILES

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

Average Molecular Weight

150.1299

Monoisotopic Molecular Weight

150.05282343

Classification

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
Beta-hydroxy ketone
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Polyol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

xylulose (CHEBI:17140 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	D-Xylulose, non-derivatized, GC-MS Spectrum	splash10-00kb-0930000000-c3a525ee2ad524114f0d	Spectrum
Predicted GC-MS	D-Xylulose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-9100000000-1304cf35b8860cd7a456	Spectrum
Predicted GC-MS	D-Xylulose, TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00g3-9127300000-b6aed5448276d0184bc2	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014r-4900000000-0a4d51584b79dc230edb	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-2131da3ca52caffed55f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-305f431957b24a5b888a	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2900000000-3e1ebc07944b3d190ec8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-9be7fcf2c9ec6f8829c7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fv-9000000000-931753afec5aa068bca8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-9400000000-1c39b6f316e1745d355c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06ri-9100000000-095c1d8c10895109ecb1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-5ea417513158cb617f30	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum