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

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Record Information
Version2.0
Created at2007-05-23 01:45:51 UTC
Updated at2024-09-17 15:44:59 UTC
NP-MRD IDNP0001369
Secondary Accession NumbersNone
Natural Product Identification
Common NameD-Glucurono-6,3-lactone
DescriptionD-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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

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


  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
Download

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

HMDB0006355
     RDKit          3D
D-Glucurono-6,3-lactone
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.4063   -1.2967    0.4303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -0.9408    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507   -1.6721    0.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152   -0.8511    0.5953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2197   -0.9626   -0.3412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1861   -1.7281    0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    0.4864   -0.4651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3768    0.7496   -1.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3496    1.0880   -0.6575 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463    0.5535    0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8559    0.4423   -0.2084 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6874    1.4007    0.3491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870   -1.0486    1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -1.4325   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5957   -1.1555    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0424    0.8255    0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442    1.7398   -1.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997    1.1855    1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8730    0.5458   -1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456    2.0710    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11  2  1  0
 10  4  1  0
  4 13  1  1
  5 14  1  6
  6 15  1  0
  7 16  1  1
  8 17  1  0
 10 18  1  1
 11 19  1  6
 12 20  1  0
M  END
Download

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


  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

$$$$
Download

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

HMDB0006355
     RDKit          3D
D-Glucurono-6,3-lactone
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.4063   -1.2967    0.4303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -0.9408    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507   -1.6721    0.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152   -0.8511    0.5953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2197   -0.9626   -0.3412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1861   -1.7281    0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    0.4864   -0.4651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3768    0.7496   -1.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3496    1.0880   -0.6575 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463    0.5535    0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8559    0.4423   -0.2084 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6874    1.4007    0.3491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870   -1.0486    1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -1.4325   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5957   -1.1555    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0424    0.8255    0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442    1.7398   -1.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997    1.1855    1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8730    0.5458   -1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456    2.0710    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11  2  1  0
 10  4  1  0
  4 13  1  1
  5 14  1  6
  6 15  1  0
  7 16  1  1
  8 17  1  0
 10 18  1  1
 11 19  1  6
 12 20  1  0
M  END
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PDB for NP0001369 (D-Glucurono-6,3-lactone)

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

COMPND    HMDB0006355
HETATM    1  O1  UNL     1       3.406  -1.297   0.430  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.229  -0.941   0.173  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.051  -1.672   0.171  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.015  -0.851   0.595  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.220  -0.963  -0.341  1.00  0.00           C  
HETATM    6  O3  UNL     1      -2.186  -1.728   0.293  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.614   0.486  -0.465  1.00  0.00           C  
HETATM    8  O4  UNL     1      -2.377   0.750  -1.587  1.00  0.00           O  
HETATM    9  O5  UNL     1      -0.350   1.088  -0.657  1.00  0.00           O  
HETATM   10  C5  UNL     1       0.446   0.553   0.332  1.00  0.00           C  
HETATM   11  C6  UNL     1       1.856   0.442  -0.208  1.00  0.00           C  
HETATM   12  O6  UNL     1       2.687   1.401   0.349  1.00  0.00           O  
HETATM   13  H1  UNL     1      -0.287  -1.049   1.638  1.00  0.00           H  
HETATM   14  H2  UNL     1      -0.963  -1.433  -1.293  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.596  -1.155   0.995  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.042   0.825   0.475  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.444   1.740  -1.661  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.400   1.185   1.251  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.873   0.546  -1.318  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.146   2.071   0.828  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4
CONECT    4    5   10   13
CONECT    5    6    7   14
CONECT    6   15
CONECT    7    8    9   16
CONECT    8   17
CONECT    9   10
CONECT   10   11   18
CONECT   11   12   19
CONECT   12   20
END
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SMILES for NP0001369 (D-Glucurono-6,3-lactone)

O[C@@H]1O[C@@H]2[C@@H](O)C(=O)O[C@@H]2[C@H]1O
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INCHI for NP0001369 (D-Glucurono-6,3-lactone)

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
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View in JSmolView NMR Assignments
Synonyms
ValueSource
D-GlucuroneHMDB
D-Glucuronic acidHMDB
D-Glucuronic acid lactoneHMDB
D-Glucurono-3,6-lactoneHMDB
D-GlucuronolactoneHMDB
DicuroneHMDB
Glucofuranurono-6,3-lactoneHMDB
GlucoxyHMDB
GlucurolactoneHMDB
GlucuronHMDB
GlucuroneHMDB
Glucuronic acid lactoneHMDB
GlucuronolactoneHMDB
GlucuronosanHMDB
GluronsanHMDB
GlycuroneHMDB
GuronsanHMDB
Reulatt s.s.HMDB
Chemical FormulaC6H8O6
Average Mass176.1241 Da
Monoisotopic Mass176.03209 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 Number32449-92-6
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 KeyOGLCQHRZUSEXNB-WHDMSYDLSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassIsosorbides
Direct ParentIsosorbides
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 FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point177.5 °CNot Available
Boiling Point403.00 to 404.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility257 mg/mL at 21 °CNot Available
LogP-3.457 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility1010 g/LALOGPS
logP-1.9ALOGPS
logP-1.9ChemAxon
logS0.76ALOGPS
pKa (Strongest Acidic)11.14ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.3 m³·mol⁻¹ChemAxon
Polarizability14.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006355
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023903
KNApSAcK IDNot Available
Chemspider ID2006482
KEGG Compound IDC02670
BioCyc IDCPD-526
BiGG ID2216733
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2724333
PDB IDNot Available
ChEBI ID18268
Good Scents IDrw1233891
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]