MiMeDB: Showing metabocard for D-Glucurono-6,3-lactone (MMDBc0047951)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:18:29 UTC

Update Date

2024-10-06 21:51:39 UTC

Metabolite ID

MMDBc0047951

Metabolite Identification

Common Name

D-Glucurono-6,3-lactone

Description

D-Glucurono-6,3-lactone belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings. D-Glucurono-6,3-lactone is a very mild and mentholic tasting compound. Glucuronolactone is a naturally occurring substance that is an important structural component of nearly all connective tissues. It is frequently used in energy drinks to increase energy levels and improve alertness, and can also be used to reduce "brain fog" caused by various medical conditions. Glucuronolactone is also found in many plant gums. Glucuronolactone is a white solid odorless compound, soluble in hot and cold water. Its melting point ranges from 176 to 178 °C. The compound can exist in a monocyclic aldehyde form or in a bicyclic hemiacetal (lactol) form. Glucuronolactone is a popular ingredient in energy drinks because it has been shown to be effective at increasing energy levels and improving alertness. Glucuronolactone supplementation also significantly reduces "brain fog" cause by various medical conditions. Although levels of glucuronolactone in energy drinks can far exceed those found in the rest of the diet, glucuronolactone is extremely safe and well tolerated. The European Food Safety Authority (EFSA) has concluded that exposure to glucuronolactone from regular consumption of energy drinks is not a safety concern.[2] The no-observed-adverse-effect level of glucuronolactone is 1000 mg/kg/day. Additionally, according to The Merck Index, glucuronolactone is used as a detoxicant. The liver uses glucose to create glucuronolactone, which inhibits the enzyme B-glucuronidase (metabolizes glucuronides), which should cause blood-glucuronide levels to rise. Glucuronides combines with toxic substances, such as morphine and depot medroxyprogesterone acetate, by converting them to water-soluble glucuronide-conjugates which are excreted in the urine. Higher blood-glucuronides help remove toxins from the body, leading to the claim that energy drinks are detoxifying. Free glucuronic acid (or its self-ester glucuronolactone) has less effect on detoxification than glucose, because the body synthesizes UDP-glucuronic acid from glucose. Therefore, sufficient carbohydrate intake provides enough UDP-glucuronic acid for detoxication, and foods rich in glucose are usually abundant in developed nations. Glucuronolactone is also metabolized to glucaric acid, xylitol, and L-xylulose, and humans may also be able to use glucuronolactone as a precursor for ascorbic acid synthesis.

Structure

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


  Mrv1652305271900072D          

 12 13  0  0  1  0            999 V2000
   12.9771   -7.4966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5464   -8.8314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7618   -7.7515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7618   -8.5765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4922   -8.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0313   -8.1640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7222   -6.7119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8013   -9.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5464   -7.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9771   -8.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6672   -8.1640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8563   -8.1640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  6  0  0  0
  3  1  1  1  0  0  0
  1  5  1  0  0  0  0
  2  4  1  0  0  0  0
  2  8  1  6  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  1  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
 11  5  2  0  0  0  0
  6 12  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047951

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O6/c7-1-3-4(12-5(1)9)2(8)6(10)11-3/h1-5,7-9H/t1-,2-,3-,4-,5-/m1/s1

> <INCHI_KEY>
OGLCQHRZUSEXNB-WHDMSYDLSA-N

> <FORMULA>
C6H8O6

> <MOLECULAR_WEIGHT>
176.1241

> <EXACT_MASS>
176.032087988

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.696856003636109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,3aR,5R,6R,6aR)-3,5,6-trihydroxy-hexahydrofuro[3,2-b]furan-2-one

> <ALOGPS_LOGP>
-1.93

> <JCHEM_LOGP>
-1.9477935553333332

> <ALOGPS_LOGS>
0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.8065345996248

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.144359248692158

> <JCHEM_PKA_STRONGEST_BASIC>
-3.959730505778521

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
32.2986

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,5R,6R,6aR)-3,5,6-trihydroxy-tetrahydro-3H-furo[3,2-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      24.224 -13.994   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.153 -16.485   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.689 -14.469   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.689 -16.009   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.319 -15.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.058 -15.239   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      23.748 -12.529   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      27.629 -17.950   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      27.153 -13.994   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      24.224 -16.485   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      21.779 -15.239   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      29.598 -15.239   0.000  0.00  0.00           O+0
CONECT    1    7    3    5                                                  
CONECT    2    4    8    6                                                  
CONECT    3    1    4    9                                                  
CONECT    4    2    3   10                                                  
CONECT    5    1   10   11                                                  
CONECT    6    2    9   12                                                  
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3    6                                                       
CONECT   10    4    5                                                       
CONECT   11    5                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Synonyms

Value	Source
D-Glucurone	HMDB
D-Glucuronic acid	HMDB
D-Glucuronic acid lactone	HMDB
D-glucurono-3,6-Lactone	HMDB
D-Glucuronolactone	HMDB
Dicurone	HMDB
glucofuranurono-6,3-Lactone	HMDB
Glucoxy	HMDB
Glucurolactone	HMDB
Glucuron	HMDB
Glucurone	HMDB
Glucuronic acid lactone	HMDB
Glucuronolactone	HMDB
Glucuronosan	HMDB
Gluronsan	HMDB
Glycurone	HMDB
Guronsan	HMDB
Reulatt s.s.	HMDB

Molecular Formula

C₆H₈O₆

Average Mass

176.1241

Monoisotopic Mass

176.032087988

IUPAC Name

(3R,3aR,5R,6R,6aR)-3,5,6-trihydroxy-hexahydrofuro[3,2-b]furan-2-one

Traditional Name

(3R,3aR,5R,6R,6aR)-3,5,6-trihydroxy-tetrahydro-3H-furo[3,2-b]furan-2-one

CAS Registry Number

32449-92-6

SMILES

O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O

InChI Identifier

InChI=1S/C6H8O6/c7-1-3-4(12-5(1)9)2(8)6(10)11-3/h1-5,7-9H/t1-,2-,3-,4-,5-/m1/s1

InChI Key

OGLCQHRZUSEXNB-WHDMSYDLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Isosorbides

Direct Parent

Isosorbides

Alternative Parents

Substituents

Isosorbide
Gamma butyrolactone
Monosaccharide
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1010 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.9	ChemAxon
logS	0.76	ALOGPS
pKa (Strongest Acidic)	11.14	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	32.3 m³·mol⁻¹	ChemAxon
Polarizability	14.7 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9300000000-ef88fbef84e17d8ed748	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-008a-4196000000-fcc76e659396761f2af0	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-0eff9b2e7506d5b5a56c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-1900000000-d1ad382f01f0d42e4d4f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c00-9600000000-e8dfa6f5abce8bd65c80	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-b0d05d510f946ae0a2f0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-1900000000-0a93ee6467e8641430d9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0r04-9200000000-2b58da5e3c60b6bf452a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-271e9efdb4dfcb70a403	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ufr-3900000000-a01bf3f9edf2268ead68	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001m-9400000000-0e2503f4cd730a8402fd	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-a0599d18157aa7371b07	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9600000000-3bac8be32b0aac93f8fa	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-8e1918514014e0eade36	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Mitochondria

Biospecimen Locations

Feces

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
MMDBp0191961	4-trimethylaminobutyraldehyde dehydrogenase	Unknown	P49189	Homo sapiens
MMDBp0191963	Alpha-aminoadipic semialdehyde dehydrogenase	Unknown	P49419	Homo sapiens
MMDBp0191964	Aldehyde dehydrogenase family 1 member A3	Unknown	P47895	Homo sapiens
MMDBp0191965	Aldehyde dehydrogenase, mitochondrial	Unknown	P05091	Homo sapiens
MMDBp0191966	Fatty aldehyde dehydrogenase	Unknown	P51648	Homo sapiens
MMDBp0191967	Aldehyde dehydrogenase X, mitochondrial	Unknown	P30837	Homo sapiens
MMDBp0195882	Dermatan-sulfate epimerase	Enzyme	Q9UL01	Homo sapiens
MMDBp0195883	D-glucuronyl C5-epimerase	Enzyme	O94923	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001309	D-Glucurono-6,3-lactone	Glucaric acid	Not Available	VMH	3779687
MMDBr0001310	D-Glucurono-6,3-lactone	Glucaric acid	aldehyde dehydrogenase 1 family, member B1	VMH	3779687
MMDBr0001333	L-Gulono-1,4-lactone	D-Glucurono-6,3-lactone	Not Available	VMH	30371894
MMDBr0002367	D-Glucuronic acid	D-Glucurono-6,3-lactone	Not Available	VMH	13587494

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0006355

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023903

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2724333

PDB ID

Not Available

ChEBI ID

18268

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

DEMOEN P, JANSSEN P, VAN DE KEERE B, ZIVKOVIC D: On the metabolic fate of isoniazide (I.N.H.) and its N2-Dglucuronolactone derivate (I.N.H.G.) (1) in man. Arch Int Pharmacodyn Ther. 1954 Aug 1;98(4):427-36. [PubMed:13208334 ]

Showing metabocard for D-Glucurono-6,3-lactone (MMDBc0047951)

MOL for #<Metabolite:0x00007fdb71dd3908>

3D MOL for #<Metabolite:0x00007fdb71dd3908>

3D SDF for #<Metabolite:0x00007fdb71dd3908>

3D-SDF for #<Metabolite:0x00007fdb71dd3908>

PDB for #<Metabolite:0x00007fdb71dd3908>

3D PDB for #<Metabolite:0x00007fdb71dd3908>

SMILES for #<Metabolite:0x00007fdb71dd3908>

INCHI for #<Metabolite:0x00007fdb71dd3908>

Structure for #<Metabolite:0x00007fdb71dd3908>

3D Structure for #<Metabolite:0x00007fdb71dd3908>