NP-MRD: Showing NP-Card for D-Glucurono-6,3-lactone (NP0001369)

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Record Information

Version

1.0

Created at

2007-05-23 01:45:51 UTC

Updated at

2021-08-19 23:59:05 UTC

NP-MRD ID

NP0001369

Secondary Accession Numbers

None

Natural Product 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>
NP0001369

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol View NMR Assignments

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

Chemical Formula

C₆H₈O₆

Average Mass

176.1241 Da

Monoisotopic Mass

176.03209 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	177.5 °C	Not Available
Boiling Point	403.00 to 404.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	257 mg/mL at 21 °C	Not Available
LogP	-3.457 (est)	The Good Scents Company Information System

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

External Links

HMDB ID

HMDB0006355

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1233891

References

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 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Patient Version. 2002. [PubMed:34403226 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:28876831 ]
Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Adult Soft Tissue Sarcoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389481 ]
Authors unspecified: Testicular Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:26389404 ]
Authors unspecified: Rectal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389402 ]
Authors unspecified: Childhood Astrocytomas Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389391 ]
Authors unspecified: Colon Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389297 ]
Hsu WH, Wang SJ, Chao YM, Chen CJ, Wang YF, Fuh JL, Chen SP, Lin YL: Urine metabolomics signatures in reversible cerebral vasoconstriction syndrome. Cephalalgia. 2020 Jun;40(7):735-747. doi: 10.1177/0333102419897621. Epub 2020 Jan 7. [PubMed:31910660 ]
Hosaka H, Mizoguchi S, Tashiro M, Fujimoto T, Hirano T, Hakamata W, Nishio T: Chemoenzymatic synthesis of sucuronic acid using d-glucurono-6,3-lactone and sucrose as raw materials, and properties of the product. Enzyme Microb Technol. 2018 Mar;110:53-60. doi: 10.1016/j.enzmictec.2017.12.006. Epub 2017 Dec 21. [PubMed:29310856 ]
Liu CT, Raghu R, Lin SH, Wang SY, Kuo CH, Tseng YJ, Sheen LY: Metabolomics of ginger essential oil against alcoholic fatty liver in mice. J Agric Food Chem. 2013 Nov 20;61(46):11231-40. doi: 10.1021/jf403523g. Epub 2013 Nov 12. [PubMed:24171385 ]
Jenkinson SF, Best D, Weymouth-Wilson AC, Clarkson RA, Fleet GW, Watkin DJ: (1S)-1,2-O-Benzyl-idene-alpha-d-glucurono-6,3-lactone. Acta Crystallogr Sect E Struct Rep Online. 2009 Jan 31;65(Pt 2):o414-5. doi: 10.1107/S1600536809002876. [PubMed:21582005 ]

Showing NP-Card for D-Glucurono-6,3-lactone (NP0001369)

MOL for NP0001369 (D-Glucurono-6,3-lactone)

3D MOL for NP0001369 (D-Glucurono-6,3-lactone)

3D SDF for NP0001369 (D-Glucurono-6,3-lactone)

3D-SDF for NP0001369 (D-Glucurono-6,3-lactone)

PDB for NP0001369 (D-Glucurono-6,3-lactone)

3D PDB for NP0001369 (D-Glucurono-6,3-lactone)

SMILES for NP0001369 (D-Glucurono-6,3-lactone)

INCHI for NP0001369 (D-Glucurono-6,3-lactone)

Structure for NP0001369 (D-Glucurono-6,3-lactone)

3D Structure for NP0001369 (D-Glucurono-6,3-lactone)