Livestock Metabolome Database: Showing metabocard for Levoglucosan (LMDB00201)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:44:35 UTC

Update Date

2016-07-20 20:57:44 UTC

Lmdb

LMDB00201

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Levoglucosan

Description

Levoglucosan is an anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose. It is formed from the pyrolysis of carbohydrates, such as starch and cellulose. As a result, levoglucosan is often used as a chemical tracer for biomass burning in atmospheric chemistry studies, particularly with respect to airborne particulate matter. Levoglucosan in urine has been shown to be highly correlated with regional fires and as a biomarker for wood smoke exposure (PMID: 19165390 ). This is because the gas emitted by the pyrolysis of wood (biomass) contains significant amounts of levoglucosan. The hydrolysis of levoglucosan generates the fermentable sugar glucose, and therefore lignocellulosic material exhibits great potential as a renewable feedstock for the production of bioethanol. Levoglucosan can also be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers. Levoglucosan is also produced via caramelization of sugar. Consumption of caramel or caramel-containing sweets can lead to a short-term 5X increase in urinary levels of Levoglucosan (from 20 uM/mM creatinine to 100 uM/mM creatinine) (PMID: 19707249 ). Urinary levoglucosan levels increase within 2 h of caramel consumption and return to pre-exposure levels within 24 h. These data suggest that diet is a major factor in determining urinary Levoglucosan levels and that recent dietary history needs to be taken into account to use Levoglucosan as a marker for wood smoke exposure. Excretory levels of Levoglucosan vary widely from zero up to 5.3 mmol/l. (PMID: 3757263 , 16448658 , 16317539 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,6-Anhydro-beta-D-glucose	ChEBI
1,6-Anhydro-beta-glucopyranose	ChEBI
1,6-Anhydroglucose	ChEBI
Glucosan	ChEBI
Leucoglucosan	ChEBI
1,6-Anhydro-b-D-glucose	Generator
1,6-Anhydro-β-D-glucose	Generator
1,6-Anhydro-b-glucopyranose	Generator
1,6-Anhydro-β-glucopyranose	Generator
1,6-Anhydro-b-D-glucopyranose	HMDB
1,6-Anhydro-beta-D-glucopyranose	HMDB
1,6-Anhydro-beta-delta-glucopyranose	HMDB
1,6-Anhydro-beta-delta-glucose	HMDB
1,6-Anhydro-D-glucose	HMDB
1,6-Anhydro-delta-glucose	HMDB
6,8-Dioxabicyclo[3.2.1]octane b-D-glucopyranose deriv.	HMDB
6,8-Dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.	HMDB
Anhydro-D-mannosan	HMDB
Anhydro-delta-mannosan	HMDB
L-Glucosan	HMDB

Chemical Formula

C₆H₁₀O₅

Average Molecular Weight

162.1406

Monoisotopic Molecular Weight

162.05282343

IUPAC Name

(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

Traditional Name

levoglucosan

CAS Registry Number

498-07-7

SMILES

[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O

InChI Identifier

InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1

InChI Key

TWNIBLMWSKIRAT-VFUOTHLCSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Oxane
Monosaccharide
Meta-dioxolane
Secondary alcohol
Oxacycle
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

anhydrohexose (CHEBI:30997 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-2.2	ALOGPS
logP	-1.8	ChemAxon
logS	0.99	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	32.41 m³·mol⁻¹	ChemAxon
Polarizability	14.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0uxr-0950000000-70ad01d41ff4333eadf9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0uxr-0891000000-57d1cb031374b05f81ee	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxr-0950000000-70ad01d41ff4333eadf9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-9700000000-c11d864b6822a2dd966b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00dr-9565000000-6d6d0dfecd366e99e4d9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0006-0900000000-ac847a3bb73d41f49c98	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-ac847a3bb73d41f49c98	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-7bb1d2984b85d3ea59f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-9000000000-ca6ed7b53ee1e2b1f81d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0900000000-ac847a3bb73d41f49c98	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0fk9-9200000000-eac1336013686b48cafc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9200000000-de7ea818bfd73e81bdc0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ap3-9000000000-6db689252d5a1dbb6616	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-64f52041bef6f8fd6303	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-01qa-1900000000-bd41a8b766dc8d62c0d8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01qa-1900000000-bd41a8b766dc8d62c0d8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4f8012fb5d2fca895d06	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-07bk-9000000000-d3f3830e72144f10cd14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05n0-9100000000-bd3e5214bd96e7ff58cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ap3-9000000000-2e6b4a130ed562483808	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05n0-9100000000-8011677f551a4270ff11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-74a6c5b8f6aa28124f0b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-14a66c38d90a0376e8f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2900000000-2046d1a11a651e07604a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-13457c8abeb48c83d2af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-2606fdba0d7add9cbef7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-9600000000-28f762ccedd56ed21a4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-7a4ff35e6bf7ab7552da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-3952c076838b2d8a44c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-0900000000-b09c5e74350b102ce94c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000640

FooDB ID

FDB112163

Phenol Explorer ID

Not Available

KNApSAcK ID

C00007411

BiGG ID

Not Available

BioCyc ID

CPD-12923

METLIN ID

5613

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

YMDB02300

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Migliaccio CT, Bergauff MA, Palmer CP, Jessop F, Noonan CW, Ward TJ: Urinary levoglucosan as a biomarker of wood smoke exposure: observations in a mouse model and in children. Environ Health Perspect. 2009 Jan;117(1):74-9. doi: 10.1289/ehp.11378. Epub 2008 Aug 15. [19165390 ]
Bergauff MA, Ward TJ, Noonan CW, Migliaccio CT, Simpson CD, Evanoski AR, Palmer CP: Urinary levoglucosan as a biomarker of wood smoke: results of human exposure studies. J Expo Sci Environ Epidemiol. 2010 Jun;20(4):385-92. doi: 10.1038/jes.2009.46. Epub 2009 Aug 26. [19707249 ]
Dorland L, Wadman SK, Fabery de Jonge H, Ketting D: 1,6-Anhydro-beta-D-glucopyranose (beta-glucosan), a constituent of human urine. Clin Chim Acta. 1986 Aug 30;159(1):11-6. [3757263 ]
Dixon RW, Baltzell G: Determination of levoglucosan in atmospheric aerosols using high performance liquid chromatography with aerosol charge detection. J Chromatogr A. 2006 Mar 24;1109(2):214-21. Epub 2006 Jan 31. [16448658 ]
Schkolnik G, Rudich Y: Detection and quantification of levoglucosan in atmospheric aerosols: a review. Anal Bioanal Chem. 2006 May;385(1):26-33. Epub 2005 Nov 30. [16317539 ]

Showing metabocard for Levoglucosan (LMDB00201)

Structure for LMDB00201 (Levoglucosan)