MiMeDB: Showing metabocard for Levoglucosan (MMDBc0000359)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:05 UTC

Update Date

2024-04-30 19:31:55 UTC

Metabolite ID

MMDBc0000359

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

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      33.131 -26.068   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.352 -27.396   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      32.371 -24.729   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      30.812 -27.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.831 -24.718   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.051 -26.046   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      34.671 -26.079   0.000  0.00  0.00           H+0
HETATM    8  O   UNK     0      33.112 -28.736   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      30.032 -28.713   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      28.511 -26.035   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      30.813 -23.379   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      33.150 -23.378   0.000  0.00  0.00           O+0
CONECT    1    2    3    7   12                                             
CONECT    2    1    4    8                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    9                                                  
CONECT    5    3    6   11                                                  
CONECT    6    4    5   10                                                  
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    5   12                                                       
CONECT   12   11    1                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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

Molecular Formula

C₆H₁₀O₅

Average Mass

162.1406

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1600 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0uxr-0891000000-57d1cb031374b05f81ee	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxr-0950000000-70ad01d41ff4333eadf9	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-9700000000-c11d864b6822a2dd966b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00dr-9565000000-6d6d0dfecd366e99e4d9	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 (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_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 (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_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_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0006-0900000000-ac847a3bb73d41f49c98	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-ac847a3bb73d41f49c98	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-7bb1d2984b85d3ea59f3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-9000000000-ca6ed7b53ee1e2b1f81d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0900000000-ac847a3bb73d41f49c98	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0fk9-9200000000-eac1336013686b48cafc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9200000000-de7ea818bfd73e81bdc0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ap3-9000000000-6db689252d5a1dbb6616	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-64f52041bef6f8fd6303	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-01qa-1900000000-bd41a8b766dc8d62c0d8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01qa-1900000000-bd41a8b766dc8d62c0d8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4f8012fb5d2fca895d06	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-07bk-9000000000-d3f3830e72144f10cd14	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05n0-9100000000-bd3e5214bd96e7ff58cb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ap3-9000000000-2e6b4a130ed562483808	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05n0-9100000000-8011677f551a4270ff11	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-74a6c5b8f6aa28124f0b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-14a66c38d90a0376e8f4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2900000000-2046d1a11a651e07604a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-13457c8abeb48c83d2af	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-2606fdba0d7add9cbef7	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-9600000000-28f762ccedd56ed21a4c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-7a4ff35e6bf7ab7552da	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-3952c076838b2d8a44c1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-0900000000-b09c5e74350b102ce94c	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0017358	Adenosine triphosphate	ADP	Levoglucosan kinase	Phosphorylation	RHEA	34755880
MMDBr0017359	Adenosine triphosphate	ADP	Levoglucosan kinase	Phosphorylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Lung cancer		Association	Human Urine	HMDB	22157537
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

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 Urine	Detected and Quantified	4.6	7.1			umol/mmol creatinine	Not Specified	Both	Lung cancer	HMDB	22157537
Human Urine	Detected and Quantified	10.1		2.4	29.6	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	19.984	17.348			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	52.785	91.707			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Blood	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0000640

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112163

KNApSAcK ID

C00007411

Chemspider ID

9587432

KEGG Compound ID

Not Available

BioCyc ID

CPD-12923

BiGG ID

Not Available

Wikipedia Link

Levoglucosan

METLIN ID

5613

PubChem Compound

2724705

PDB ID

Not Available

ChEBI ID

30997

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0009-8981(86)90161-0. [PubMed:3757263 ]
Schkolnik G, Rudich Y: Detection and quantification of levoglucosan in atmospheric aerosols: a review. Anal Bioanal Chem. 2006 May;385(1):26-33. doi: 10.1007/s00216-005-0168-5. Epub 2005 Nov 30. [PubMed:16317539 ]
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. doi: 10.1016/j.chroma.2006.01.021. Epub 2006 Jan 31. [PubMed:16448658 ]
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. [PubMed: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. [PubMed:19707249 ]

Showing metabocard for Levoglucosan (MMDBc0000359)

MOL for #<Metabolite:0x00007f56081d8db8>

3D MOL for #<Metabolite:0x00007f56081d8db8>

3D SDF for #<Metabolite:0x00007f56081d8db8>

3D-SDF for #<Metabolite:0x00007f56081d8db8>

PDB for #<Metabolite:0x00007f56081d8db8>

3D PDB for #<Metabolite:0x00007f56081d8db8>

SMILES for #<Metabolite:0x00007f56081d8db8>

INCHI for #<Metabolite:0x00007f56081d8db8>

Structure for #<Metabolite:0x00007f56081d8db8>

3D Structure for #<Metabolite:0x00007f56081d8db8>