Showing metabocard for Levoglucosan (MMDBc0000359)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:05 UTC
Update Date2022-08-31 06:02:32 UTC
Metabolite IDMMDBc0000359
Metabolite Identification
Common NameLevoglucosan
DescriptionLevoglucosan 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be05e72b0>


  Mrv1652304202019212D          

 12 13  0  0  1  0            999 V2000
   17.7488  -13.9652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3312  -14.6766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3415  -13.2477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5062  -14.6707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5165  -13.2418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0988  -13.9532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5738  -13.9711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7385  -15.3941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0885  -15.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2739  -13.9473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5067  -12.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7587  -12.5239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  6  0  0  0
  2  8  1  6  0  0  0
  4  9  1  1  0  0  0
  6 10  1  6  0  0  0
  5 11  1  1  0  0  0
 12 11  1  0  0  0  0
  1 12  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x0000560be05e72b0>

HMDB0000640
     RDKit          3D
Levoglucosan
 21 22  0  0  0  0  0  0  0  0999 V2000
   -0.1943   -2.4874    0.5039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.1180    0.4033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1043   -0.4779    0.3216 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9278   -0.8365    1.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8664    1.0146    0.2187 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0223    1.7529    0.1937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    1.2447   -0.9790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3120    1.6064   -0.6368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    0.4476   -0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0486   -0.6461   -0.8059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2261    0.0529   -1.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -2.7412    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529   -0.6558    1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -0.7866   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211   -1.0751    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976    1.2928    1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449    2.1616    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    1.9675   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674    0.3339    0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8140    0.4261   -1.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788   -1.4766   -1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10  2  1  0
 11  7  1  0
  1 12  1  0
  2 13  1  1
  3 14  1  6
  4 15  1  0
  5 16  1  1
  6 17  1  0
  7 18  1  6
  9 19  1  0
  9 20  1  0
 10 21  1  6
M  END
Download

3D SDF for #<Metabolite:0x0000560be05e72b0>


  Mrv1652304202019212D          

 12 13  0  0  1  0            999 V2000
   17.7488  -13.9652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3312  -14.6766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3415  -13.2477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5062  -14.6707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5165  -13.2418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0988  -13.9532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5738  -13.9711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7385  -15.3941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0885  -15.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2739  -13.9473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5067  -12.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7587  -12.5239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  6  0  0  0
  2  8  1  6  0  0  0
  4  9  1  1  0  0  0
  6 10  1  6  0  0  0
  5 11  1  1  0  0  0
 12 11  1  0  0  0  0
  1 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000359

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C6H10O5

> <MOLECULAR_WEIGHT>
162.1406

> <EXACT_MASS>
162.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.130250612602248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.18

> <JCHEM_LOGP>
-1.7708356456666667

> <ALOGPS_LOGS>
0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.215582381313808

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.212605412524747

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6486679661074968

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
32.41329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
levoglucosan

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x0000560be05e72b0>

HMDB0000640
     RDKit          3D
Levoglucosan
 21 22  0  0  0  0  0  0  0  0999 V2000
   -0.1943   -2.4874    0.5039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.1180    0.4033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1043   -0.4779    0.3216 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9278   -0.8365    1.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8664    1.0146    0.2187 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0223    1.7529    0.1937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    1.2447   -0.9790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3120    1.6064   -0.6368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    0.4476   -0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0486   -0.6461   -0.8059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2261    0.0529   -1.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -2.7412    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529   -0.6558    1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -0.7866   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211   -1.0751    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976    1.2928    1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449    2.1616    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    1.9675   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674    0.3339    0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8140    0.4261   -1.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788   -1.4766   -1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10  2  1  0
 11  7  1  0
  1 12  1  0
  2 13  1  1
  3 14  1  6
  4 15  1  0
  5 16  1  1
  6 17  1  0
  7 18  1  6
  9 19  1  0
  9 20  1  0
 10 21  1  6
M  END
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PDB for #<Metabolite:0x0000560be05e72b0>

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
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3D PDB for #<Metabolite:0x0000560be05e72b0>

COMPND    HMDB0000640
HETATM    1  O1  UNL     1      -0.194  -2.487   0.504  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.276  -1.118   0.403  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.104  -0.478   0.322  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.928  -0.836   1.351  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.866   1.015   0.219  1.00  0.00           C  
HETATM    6  O3  UNL     1       2.022   1.753   0.194  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.026   1.245  -0.979  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.312   1.606  -0.637  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.047   0.448  -0.445  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.049  -0.646  -0.806  1.00  0.00           C  
HETATM   11  O5  UNL     1      -0.226   0.053  -1.710  1.00  0.00           O  
HETATM   12  H1  UNL     1      -0.538  -2.741   1.416  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.753  -0.656   1.317  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.510  -0.787  -0.686  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.821  -1.075   0.943  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.298   1.293   1.151  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.245   2.162   1.088  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.487   1.968  -1.639  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.467   0.334   0.552  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.814   0.426  -1.265  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.579  -1.477  -1.293  1.00  0.00           H  
CONECT    1    2   12
CONECT    2    3   10   13
CONECT    3    4    5   14
CONECT    4   15
CONECT    5    6    7   16
CONECT    6   17
CONECT    7    8   11   18
CONECT    8    9
CONECT    9   10   19   20
CONECT   10   11   21
END
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SMILES for #<Metabolite:0x0000560be05e72b0>

[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O
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INCHI for #<Metabolite:0x0000560be05e72b0>

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
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Synonyms
ValueSource
1,6-Anhydro-beta-D-glucoseChEBI
1,6-Anhydro-beta-glucopyranoseChEBI
1,6-AnhydroglucoseChEBI
GlucosanChEBI
LeucoglucosanChEBI
1,6-Anhydro-b-D-glucoseGenerator
1,6-Anhydro-β-D-glucoseGenerator
1,6-Anhydro-b-glucopyranoseGenerator
1,6-Anhydro-β-glucopyranoseGenerator
1,6-Anhydro-b-D-glucopyranoseHMDB
1,6-Anhydro-beta-D-glucopyranoseHMDB
1,6-Anhydro-beta-delta-glucopyranoseHMDB
1,6-Anhydro-beta-delta-glucoseHMDB
1,6-Anhydro-D-glucoseHMDB
1,6-Anhydro-delta-glucoseHMDB
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-mannosanHMDB
Anhydro-delta-mannosanHMDB
L-GlucosanHMDB
Molecular FormulaC6H10O5
Average Mass162.1406
Monoisotopic Mass162.05282343
IUPAC Name(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
Traditional Namelevoglucosan
CAS Registry NumberNot 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 KeyTWNIBLMWSKIRAT-VFUOTHLCSA-N