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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:02:59 UTC

Update Date

2021-09-26 22:57:50 UTC

HMDB ID

HMDB0247896

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Glucaron

Description

Glucaron belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Based on a literature review a small amount of articles have been published on Glucaron. This compound has been identified in human blood as reported by (PMID: 31557052 ). Glucaron is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Glucaron is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652309112103032D          

 18 19  0  0  0  0            999 V2000
   -1.3168   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139   -1.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242    0.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312    0.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861    1.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1832    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247896

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1C2OC(=O)C(OC(C)=O)C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O8/c1-3(11)15-7-5-6(18-9(7)13)8(10(14)17-5)16-4(2)12/h5-8H,1-2H3

> <INCHI_KEY>
ZOZKYEHVNDEUCO-UHFFFAOYSA-N

> <FORMULA>
C10H10O8

> <MOLECULAR_WEIGHT>
258.182

> <EXACT_MASS>
258.037567282

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.1000291025183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(acetyloxy)-2,5-dioxo-hexahydrofuro[3,2-b]furan-3-yl acetate

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
-0.8782767026666668

> <ALOGPS_LOGS>
-0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.848256610768729

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.36341662397897

> <JCHEM_PKA_STRONGEST_BASIC>
-6.593622069747966

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
49.457000000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aceglatone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.458  -5.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.982  -4.277   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.013  -3.132   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.476  -3.956   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.374  -1.246   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.929  -2.492   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.405   1.465   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.911   1.785   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.387   3.249   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.942   0.640   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.445  -1.246   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    7   17                                                       
CONECT   17   16    5   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0247896
HETATM    1  C1  UNL     1      -5.351  -0.030   0.201  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.055  -0.297  -0.461  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.005  -0.552  -1.685  1.00  0.00           O  
HETATM    4  O2  UNL     1      -2.893  -0.270   0.251  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.618  -0.503  -0.255  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.888  -1.604   0.388  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.285  -2.633   0.983  1.00  0.00           O  
HETATM    8  O4  UNL     1       0.466  -1.311   0.228  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.645  -0.067  -0.396  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.656   0.808   0.325  1.00  0.00           C  
HETATM   11  O5  UNL     1       2.798   0.065   0.643  1.00  0.00           O  
HETATM   12  C7  UNL     1       4.071   0.337   0.165  1.00  0.00           C  
HETATM   13  C8  UNL     1       5.267  -0.443   0.498  1.00  0.00           C  
HETATM   14  O6  UNL     1       4.187   1.324  -0.607  1.00  0.00           O  
HETATM   15  C9  UNL     1       0.878   1.223   1.516  1.00  0.00           C  
HETATM   16  O7  UNL     1       1.361   1.713   2.558  1.00  0.00           O  
HETATM   17  O8  UNL     1      -0.468   0.978   1.286  1.00  0.00           O  
HETATM   18  C10 UNL     1      -0.660   0.638  -0.078  1.00  0.00           C  
HETATM   19  H1  UNL     1      -5.871   0.837  -0.293  1.00  0.00           H  
HETATM   20  H2  UNL     1      -6.028  -0.917   0.173  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.217   0.247   1.263  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.700  -0.714  -1.329  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.845  -0.133  -1.477  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.871   1.658  -0.364  1.00  0.00           H  
HETATM   25  H7  UNL     1       6.157   0.219   0.432  1.00  0.00           H  
HETATM   26  H8  UNL     1       5.242  -0.787   1.571  1.00  0.00           H  
HETATM   27  H9  UNL     1       5.451  -1.286  -0.199  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.857   1.501  -0.718  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   18   22
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   18   23
CONECT   10   11   15   24
CONECT   11   12
CONECT   12   13   14   14
CONECT   13   25   26   27
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,5-Di-O-acetyl glucaro-(1,4)-(6-3)-dilactone	HMDB
Aceglatone monosodium salt	HMDB
Diacetyl glucaro-(1,4)-(6-3)-dilactone	HMDB

Chemical Formula

C₁₀H₁₀O₈

Average Molecular Weight

258.182

Monoisotopic Molecular Weight

258.037567282

IUPAC Name

6-(acetyloxy)-2,5-dioxo-hexahydrofuro[3,2-b]furan-3-yl acetate

Traditional Name

aceglatone

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C2OC(=O)C(OC(C)=O)C2OC1=O

InChI Identifier

InChI=1S/C10H10O8/c1-3(11)15-7-5-6(18-9(7)13)8(10(14)17-5)16-4(2)12/h5-8H,1-2H3

InChI Key

ZOZKYEHVNDEUCO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Isosorbide
Furofuran
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.35	ALOGPS
logP	-0.88	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	15.36	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.46 m³·mol⁻¹	ChemAxon
Polarizability	22.1 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.916	30932474
DeepCCS	[M-H]-	145.52	30932474
DeepCCS	[M-2H]-	178.655	30932474
DeepCCS	[M+Na]+	153.832	30932474
AllCCS	[M+H]+	155.4	32859911
AllCCS	[M+H-H2O]+	151.9	32859911
AllCCS	[M+NH4]+	158.7	32859911
AllCCS	[M+Na]+	159.7	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	154.9	32859911
AllCCS	[M+HCOO]-	154.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glucaron	CC(=O)OC1C2OC(=O)C(OC(C)=O)C2OC1=O	3181.3	Standard polar	33892256
Glucaron	CC(=O)OC1C2OC(=O)C(OC(C)=O)C2OC1=O	1740.0	Standard non polar	33892256
Glucaron	CC(=O)OC1C2OC(=O)C(OC(C)=O)C2OC1=O	1941.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glucaron GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-9720000000-13d46c385ac8c4b41ad0	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glucaron GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucaron 10V, Positive-QTOF	splash10-0a4i-0090000000-5cf880927b16820fc944	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucaron 20V, Positive-QTOF	splash10-0a4l-0690000000-63c8e1ce1f735636f02d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucaron 40V, Positive-QTOF	splash10-0006-9710000000-bd6f1daa3f9cfa72d980	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucaron 10V, Negative-QTOF	splash10-0a4i-0390000000-b171e1a56069533b780f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucaron 20V, Negative-QTOF	splash10-0a4l-4950000000-cdd2a93c09cab2179916	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucaron 40V, Negative-QTOF	splash10-0a4l-9100000000-dc27b279bc4e18c46076	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1903

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aceglatone

METLIN ID

Not Available

PubChem Compound

1980

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Glucaron (HMDB0247896)

MOL for HMDB0247896 (Glucaron)

3D MOL for HMDB0247896 (Glucaron)

3D SDF for HMDB0247896 (Glucaron)

3D-SDF for HMDB0247896 (Glucaron)

PDB for HMDB0247896 (Glucaron)

3D PDB for HMDB0247896 (Glucaron)

SMILES for HMDB0247896 (Glucaron)

INCHI for HMDB0247896 (Glucaron)

Structure for HMDB0247896 (Glucaron)

3D Structure for HMDB0247896 (Glucaron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra