Showing metabocard for Gluconolactone (MMDBc0029475)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:23:46 UTC
Update Date2024-10-07 00:12:48 UTC
Metabolite IDMMDBc0029475
Metabolite Identification
Common NameGluconolactone
DescriptionGluconolactone is a lactone or oxidized derivative of glucose. Gluconolactone is a polyhydroxy acid (PHA) that is capable of chelating metals and may also function by scavenging free radicals. When dissolved in water, it is partially hydrolysed to gluconic acid, with the balance between the lactone form and the acid form established as a chemical equilibrium. The rate of hydrolysis of gluconolactone is increased by heat and high pH. It is an intermediate in glucose and glucose-1-phosphate degradation.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f92038b0730>


  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 #<Metabolite:0x00007f92038b0730>

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 #<Metabolite:0x00007f92038b0730>


  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>
MMDBc0029475

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007f92038b0730>

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 #<Metabolite:0x00007f92038b0730>

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
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3D PDB for #<Metabolite:0x00007f92038b0730>

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
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SMILES for #<Metabolite:0x00007f92038b0730>

OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
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INCHI for #<Metabolite:0x00007f92038b0730>

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
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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)MeSH, HMDB
Glucono-delta-lactoneMeSH
(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
GluconolactoneHMDB
LysactoneHMDB
Molecular FormulaC6H10O6
Average Mass178.14
Monoisotopic Mass178.047738052
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