Np mrd loader

Showing NP-Card for Gluconolactone (NP0000171)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-07-01 14:27:13 UTC
NP-MRD IDNP0000171
Secondary Accession NumbersNone
Natural Product Identification
Common NameGluconolactone
DescriptionGluconolactone, also known as glucono-delta-lactone or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids (PHAs) containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is a lactone of D-gluconic acid. Gluconolactone can be produced by enzymatic oxidation of D-glucose via the enzyme glucose oxidase. It is a fundamental metabolite found in all organisms ranging from bacteria to plants to animals. Gluconolactone has metal chelating, moisturizing and antioxidant activities. Its ability in free radicals scavenging accounts for its antioxidant properties. Gluconolactone, is also used as a food additive with the E-number E575. In foods it is used as a sequestrant, an acidifier or a curing, pickling, or leavening agent. Gluconolactone is also used as a coagulant in tofu processing. Gluconolactone is widely used as a skin exfoliant in cosmetic products, where it is noted for its mild exfoliating and hydrating properties. Pure gluconolactone is a white odorless crystalline powder. It is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods. Gluconic acid has roughly a third of the sourness of citric acid. One gram of gluconolactone yields roughly the same amount of metabolic energy as one gram of sugar.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000171 (Gluconolactone)


  Mrv1652309182018142D          

 12 12  0  0  1  0            999 V2000
   -2.1436    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4290   -0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4290   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  6  0  0  0
M  END
Download

3D MOL for NP0000171 (Gluconolactone)

HMDB0000150
     RDKit          3D
Gluconolactone
 22 22  0  0  0  0  0  0  0  0999 V2000
   -1.4684   -1.1685   -2.5741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029   -0.9008   -1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4729   -0.8258   -1.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838    0.2110   -0.5060 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4694    0.0811   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288   -1.0870    0.3392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    0.3220    0.8353 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6365    1.5906    1.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2122    0.3339    0.6916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7539    0.0615    1.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7389   -0.6596   -0.2761 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9959   -0.2258   -0.7080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8327    1.2082   -1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513    0.9383    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    0.1014   -1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249   -1.3630    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510   -0.4255    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450    2.2201    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247    1.3556    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1980    0.8449    2.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9170   -1.6471    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5347   -0.9652   -1.0835 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
  4  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  2  1  0
  4 13  1  6
  5 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  1
  8 18  1  0
  9 19  1  6
 10 20  1  0
 11 21  1  1
 12 22  1  0
M  END
Download

3D SDF for NP0000171 (Gluconolactone)


  Mrv1652309182018142D          

 12 12  0  0  1  0            999 V2000
   -2.1436    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4290   -0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4290   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000171

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1

> <INCHI_KEY>
PHOQVHQSTUBQQK-SQOUGZDYSA-N

> <FORMULA>
C6H10O6

> <MOLECULAR_WEIGHT>
178.14

> <EXACT_MASS>
178.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.534152193627445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one

> <ALOGPS_LOGP>
-2.16

> <JCHEM_LOGP>
-2.745273186

> <ALOGPS_LOGS>
0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.052238160862654

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.618472493037629

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98908460439549

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
34.7788

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.86e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gluconolactone

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000171 (Gluconolactone)

HMDB0000150
     RDKit          3D
Gluconolactone
 22 22  0  0  0  0  0  0  0  0999 V2000
   -1.4684   -1.1685   -2.5741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029   -0.9008   -1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4729   -0.8258   -1.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838    0.2110   -0.5060 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4694    0.0811   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288   -1.0870    0.3392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    0.3220    0.8353 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6365    1.5906    1.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2122    0.3339    0.6916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7539    0.0615    1.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7389   -0.6596   -0.2761 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9959   -0.2258   -0.7080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8327    1.2082   -1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513    0.9383    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    0.1014   -1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249   -1.3630    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510   -0.4255    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450    2.2201    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5247    1.3556    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1980    0.8449    2.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9170   -1.6471    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5347   -0.9652   -1.0835 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
  4  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  2  1  0
  4 13  1  6
  5 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  1
  8 18  1  0
  9 19  1  6
 10 20  1  0
 11 21  1  1
 12 22  1  0
M  END
Download

PDB for NP0000171 (Gluconolactone)

HEADER    PROTEIN                                 18-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-20         0                                  
HETATM    1  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for NP0000171 (Gluconolactone)

COMPND    HMDB0000150
HETATM    1  O1  UNL     1      -1.468  -1.169  -2.574  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.903  -0.901  -1.459  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.473  -0.826  -1.308  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.984   0.211  -0.506  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.469   0.081  -0.284  1.00  0.00           C  
HETATM    6  O3  UNL     1       2.829  -1.087   0.339  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.287   0.322   0.835  1.00  0.00           C  
HETATM    8  O4  UNL     1       0.636   1.591   1.345  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.212   0.334   0.692  1.00  0.00           C  
HETATM   10  O5  UNL     1      -1.754   0.062   1.950  1.00  0.00           O  
HETATM   11  C6  UNL     1      -1.739  -0.660  -0.276  1.00  0.00           C  
HETATM   12  O6  UNL     1      -2.996  -0.226  -0.708  1.00  0.00           O  
HETATM   13  H1  UNL     1       0.833   1.208  -1.006  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.851   0.938   0.273  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.964   0.101  -1.296  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.725  -1.363   0.011  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.651  -0.426   1.562  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.545   2.220   0.572  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.525   1.356   0.351  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.198   0.845   2.353  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.917  -1.647   0.218  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.535  -0.965  -1.084  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4
CONECT    4    5    7   13
CONECT    5    6   14   15
CONECT    6   16
CONECT    7    8    9   17
CONECT    8   18
CONECT    9   10   11   19
CONECT   10   20
CONECT   11   12   21
CONECT   12   22
END
Download

SMILES for NP0000171 (Gluconolactone)

OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
Download

INCHI for NP0000171 (Gluconolactone)

InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-oneChEBI
1,5-D-GluconolactoneChEBI
1,5-GluconolactoneChEBI
D-AldonolactoneChEBI
D-Gluconic acid delta-lactoneChEBI
D-Gluconic acid lactoneChEBI
D-GluconolactoneChEBI
D-Threo-aldono-1,5-lactoneChEBI
delta-D-GluconolactoneChEBI
delta-GluconolactoneChEBI
GlucarolactoneChEBI
Gluconic acid lactoneChEBI
Gluconic delta-lactoneChEBI
Gluconic lactoneChEBI
D-Gluconate delta-lactoneGenerator
D-Gluconate δ-lactoneGenerator
D-Gluconic acid δ-lactoneGenerator
D-Gluconate lactoneGenerator
Δ-D-gluconolactoneGenerator
Δ-gluconolactoneGenerator
Gluconate lactoneGenerator
Gluconic δ-lactoneGenerator
1,5-delta-GluconolactoneHMDB
3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-oneHMDB
D-(+)-Gluconic acid D-lactoneHMDB
D-(+)-Gluconic acid-delta lactoneHMDB
D-delta-GluconolactoneHMDB
D-Gluconic acid 1,5-lactoneHMDB
D-Gluconic acid D-lactoneHMDB
D-Gluconic acid-1,5-lactoneHMDB
D-Gluconic acid-delta-lactoneHMDB
D-Gluconic delta-lactoneHMDB
D-Glucono-1,5-lactoneHMDB
D-Glucono-D-lactoneHMDB
delta-(+)-Gluconic acid D-lactoneHMDB
delta-AldonolactoneHMDB
delta-Gluconic acid 1,5-lactoneHMDB
delta-Gluconic acid D-lactoneHMDB
delta-Gluconic acid lactoneHMDB
delta-Gluconic acid-1,5-lactoneHMDB
delta-Glucono-1,5-lactoneHMDB
FujigluconHMDB
Gluconate, lactoneHMDB
Glucono 1,5-lactoneHMDB
Glucono delta lactoneHMDB
Glucono delta-lactoneHMDB
GDL (Gluconate)HMDB
Glucono-delta-lactoneHMDB
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-oneHMDB
D-(+)-Gluconic acid delta-lactoneHMDB
D-(+)-Gluconic acid δ-lactoneHMDB
D-(+)-Glucono-1,5-lactoneHMDB
D-(+)-Glucono-delta-lactoneHMDB
D-(+)-Glucono-δ-lactoneHMDB
D-(+)-Glucose delta-lactoneHMDB
D-(+)-Glucose δ-lactoneHMDB
D-Glucono-delta-lactoneHMDB
D-Glucono-δ-lactoneHMDB
Glucono-δ-lactoneHMDB
LysactoneHMDB
GluconolactoneHMDB
Chemical FormulaC6H10O6
Average Mass178.1400 Da
Monoisotopic Mass178.04774 Da
IUPAC Name(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
Traditional Namegluconolactone
CAS Registry Number90-80-2
SMILES
OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1
InChI KeyPHOQVHQSTUBQQK-SQOUGZDYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-07-26View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
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
Hyacinthoides non-scriptaLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lotus creticusLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Solanum lycopersicumLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tetranychus urticaeLOTUS Database
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGluconolactones
Alternative Parents
Substituents
  • Gluconolactone
  • Delta valerolactone
  • Delta_valerolactone
  • Oxane
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point151 - 155 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility590 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility586 g/LALOGPS
logP-2.2ALOGPS
logP-2.7ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)11.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.78 m³·mol⁻¹ChemAxon
Polarizability15.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000150
DrugBank IDDB04564
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001245
KNApSAcK IDC00050464
Chemspider ID6760
KEGG Compound IDC00198
BioCyc IDGLC-D-LACTONE
BiGG IDNot Available
Wikipedia LinkGluconolactone
METLIN ID353
PubChem Compound7027
PDB IDNot Available
ChEBI ID16217
Good Scents IDrw1234591
References
General References
  1. Rakotomanga S, Baillet A, Pellerin F, Baylocq-Ferrier D: Simultaneous determination of gluconolactone, galactonolactone and galactitol in urine by reversed-phase liquid chromatography: application to galactosemia. J Chromatogr. 1991 Oct 4;570(2):277-84. [PubMed:1797843 ]
  2. Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13. [PubMed:3128683 ]
  3. Hunt MJ, Barnetson RS: A comparative study of gluconolactone versus benzoyl peroxide in the treatment of acne. Australas J Dermatol. 1992;33(3):131-4. [PubMed:1303072 ]
  4. Steinberg KK, Needham LL: A comparison of two methods for quantifying D-glucaric acid. J Anal Toxicol. 1986 Jul-Aug;10(4):139-41. [PubMed:3747452 ]
  5. Friedrich T, Strohdeicher M, Hofhaus G, Preis D, Sahm H, Weiss H: The same domain motif for ubiquinone reduction in mitochondrial or chloroplast NADH dehydrogenase and bacterial glucose dehydrogenase. FEBS Lett. 1990 Jun 4;265(1-2):37-40. [PubMed:2142103 ]
  6. Puri RN, Zhou FX, Colman RF, Colman RW: Plasmin-induced platelet aggregation is accompanied by cleavage of aggregin and indirectly mediated by calpain. Am J Physiol. 1990 Dec;259(6 Pt 1):C862-8. [PubMed:2148055 ]
  7. van Weely S, Brandsma M, Strijland A, Tager JM, Aerts JM: Demonstration of the existence of a second, non-lysosomal glucocerebrosidase that is not deficient in Gaucher disease. Biochim Biophys Acta. 1993 Mar 24;1181(1):55-62. [PubMed:8457606 ]
  8. MacNeil ML, Steinberg KK, Yeager PR, Smith SJ: A semiautomated procedure for urinary D-glucaric acid using a centrifugal analyzer. J Anal Toxicol. 1986 Jan-Feb;10(1):15-7. [PubMed:3951202 ]