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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 01:45:51 UTC

Update Date

2023-02-21 17:17:17 UTC

HMDB ID

HMDB0006355

Secondary Accession Numbers

HMDB06355

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>
HMDB0006355

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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 Molecular Weight

176.1241

Monoisotopic Molecular Weight

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

Ontology

Cellular substructure

Cytoplasm (HMDB: HMDB0006355)

Organelle

Endoplasmic reticulum (HMDB: HMDB0006355)
Mitochondrion (HMDB: HMDB0006355)

Source

Endogenous

Endogenous (HMDB: HMDB0006355)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.794	31661259
DarkChem	[M-H]-	136.972	31661259
DeepCCS	[M+H]+	138.484	30932474
DeepCCS	[M-H]-	136.088	30932474
DeepCCS	[M-2H]-	170.964	30932474
DeepCCS	[M+Na]+	145.334	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.1	32859911
AllCCS	[M+NH4]+	143.6	32859911
AllCCS	[M+Na]+	144.8	32859911
AllCCS	[M-H]-	130.9	32859911
AllCCS	[M+Na-2H]-	131.5	32859911
AllCCS	[M+HCOO]-	132.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Glucurono-6,3-lactone	O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O	2941.4	Standard polar	33892256
D-Glucurono-6,3-lactone	O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O	1681.6	Standard non polar	33892256
D-Glucurono-6,3-lactone	O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O	1552.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Glucurono-6,3-lactone,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O	1706.0	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,1TMS,isomer #2	C[Si](C)(C)O[C@H]1C(=O)O[C@H]2[C@@H]1O[C@@H](O)[C@@H]2O	1695.4	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@H]2OC(=O)[C@H](O)[C@H]2O[C@H]1O	1686.8	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1O[C@@H]2[C@@H](O[Si](C)(C)C)C(=O)O[C@@H]2[C@H]1O	1816.1	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,2TMS,isomer #2	C[Si](C)(C)O[C@@H]1O[C@H]2[C@H](OC(=O)[C@@H]2O)[C@H]1O[Si](C)(C)C	1802.0	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,2TMS,isomer #3	C[Si](C)(C)O[C@H]1C(=O)O[C@H]2[C@@H]1O[C@@H](O)[C@@H]2O[Si](C)(C)C	1815.4	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,3TMS,isomer #1	C[Si](C)(C)O[C@@H]1O[C@H]2[C@H](OC(=O)[C@@H]2O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1877.4	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O	1957.0	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C(=O)O[C@H]2[C@@H]1O[C@@H](O)[C@@H]2O	1938.0	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H]2OC(=O)[C@H](O)[C@H]2O[C@H]1O	1953.0	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1O[C@@H]2[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[C@@H]2[C@H]1O	2263.8	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1O[C@H]2[C@H](OC(=O)[C@@H]2O)[C@H]1O[Si](C)(C)C(C)(C)C	2266.0	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C(=O)O[C@H]2[C@@H]1O[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C	2264.9	Semi standard non polar	33892256
D-Glucurono-6,3-lactone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1O[C@H]2[C@H](OC(=O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2566.0	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 - D-Glucurono-6,3-lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9300000000-ef88fbef84e17d8ed748	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Glucurono-6,3-lactone GC-MS (3 TMS) - 70eV, Positive	splash10-008a-4196000000-fcc76e659396761f2af0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Glucurono-6,3-lactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Glucurono-6,3-lactone 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 - D-Glucurono-6,3-lactone 10V, Positive-QTOF	splash10-004i-0900000000-0eff9b2e7506d5b5a56c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 20V, Positive-QTOF	splash10-056r-1900000000-d1ad382f01f0d42e4d4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 40V, Positive-QTOF	splash10-0c00-9600000000-e8dfa6f5abce8bd65c80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 10V, Negative-QTOF	splash10-004i-1900000000-b0d05d510f946ae0a2f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 20V, Negative-QTOF	splash10-056r-1900000000-0a93ee6467e8641430d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 40V, Negative-QTOF	splash10-0r04-9200000000-2b58da5e3c60b6bf452a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 10V, Positive-QTOF	splash10-004i-0900000000-271e9efdb4dfcb70a403	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 20V, Positive-QTOF	splash10-0ufr-3900000000-a01bf3f9edf2268ead68	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 40V, Positive-QTOF	splash10-001m-9400000000-0e2503f4cd730a8402fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 10V, Negative-QTOF	splash10-004i-0900000000-a0599d18157aa7371b07	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 20V, Negative-QTOF	splash10-004i-9600000000-3bac8be32b0aac93f8fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Glucurono-6,3-lactone 40V, Negative-QTOF	splash10-0006-9200000000-8e1918514014e0eade36	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Endoplasmic reticulum

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

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

VMH ID

GLAC

MarkerDB ID

Not Available

Good Scents ID

rw1233891

References

Synthesis Reference

Hiroto Chaen, Toshiki Tsuchioka, Tadashi Yamaguchi, Kunihiko Yuuen. Process for producing D-glucuronolactone. 1998, Eur. Pat. Appl. EP0864580A2

Material Safety Data Sheet (MSDS)

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 ]

Enzymes

Enzyme Details

1. 4-trimethylaminobutyraldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:: ALDH9A1
Uniprot ID:: P49189
Molecular weight:: 56291.485

Reactions

D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Ion	details

Enzyme Details

2. Alpha-aminoadipic semialdehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:: ALDH7A1
Uniprot ID:: P49419
Molecular weight:: 58486.74

Reactions

D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Ion	details

Enzyme Details

3. Aldehyde dehydrogenase family 1 member A3

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:: ALDH1A3
Uniprot ID:: P47895
Molecular weight:: 56107.995

Enzyme Details

4. Aldehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P05091
Molecular weight:: 56380.93

Reactions

D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Ion	details

Enzyme Details

5. Fatty aldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:: ALDH3A2
Uniprot ID:: P51648
Molecular weight:: 54847.36

Reactions

D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Ion	details

Enzyme Details

6. Aldehyde dehydrogenase X, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:: ALDH1B1
Uniprot ID:: P30837
Molecular weight:: 57248.96

Reactions

D-Glucurono-6,3-lactone + NAD + Water → Glucaric acid + NADH + Hydrogen Ion	details

Enzyme Details

7. Dermatan-sulfate epimerase

General function:: Involved in chondroitin-glucuronate 5-epimerase activity
Specific function:: Converts D-glucuronic acid to L-iduronic acid (IdoUA) residues.
Gene Name:: DSE
Uniprot ID:: Q9UL01
Molecular weight:: 109772.235

Enzyme Details

8. D-glucuronyl C5-epimerase

General function:: Involved in racemase and epimerase activity, acting on carbohydrates and derivatives
Specific function:: Converts D-glucuronic acid residues adjacent to N- sulfate sugar residues to L-iduronic acids
Gene Name:: GLCE
Uniprot ID:: O94923
Molecular weight:: 70100.5

Showing metabocard for D-Glucurono-6,3-lactone (HMDB0006355)

MOL for HMDB0006355 (D-Glucurono-6,3-lactone)

3D MOL for HMDB0006355 (D-Glucurono-6,3-lactone)

3D SDF for HMDB0006355 (D-Glucurono-6,3-lactone)

3D-SDF for HMDB0006355 (D-Glucurono-6,3-lactone)

PDB for HMDB0006355 (D-Glucurono-6,3-lactone)

3D PDB for HMDB0006355 (D-Glucurono-6,3-lactone)

SMILES for HMDB0006355 (D-Glucurono-6,3-lactone)

INCHI for HMDB0006355 (D-Glucurono-6,3-lactone)

Structure for HMDB0006355 (D-Glucurono-6,3-lactone)

3D Structure for HMDB0006355 (D-Glucurono-6,3-lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

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