Showing metabocard for Galactonolactone (MMDBc0030372)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:05:41 UTC
Update Date2022-08-31 17:49:51 UTC
Metabolite IDMMDBc0030372
Metabolite Identification
Common NameGalactonolactone
DescriptionGalactonolactone is a lactone formed from galactonic acid/galactonate. There are different isomers of galactonolactone, including structural isomers with different numbers of carbons in the lactone ring (up to 6 carbons), and also D/L enantiomers for certain structural isomers. (ChEBI, PubChem, inferred from compound structures) In E. coli, both the D and L enantiomers of galactono-1,4-lactone (with 4 carbons in the lactone ring) can be found. (EcoCyc) D-galactono-1,5-lactone (with 5 carbons in the lactone ring) has been shown to have a strong inhibitory effect on E. coli beta-galactosidase. (PMID 3109465 )
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be1dc5170>


  Mrv0541 02231219332D          

 12 12  0  0  1  0            999 V2000
   20.1379  -10.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8064   -9.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6357  -10.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1379   -7.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1742   -8.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6357   -7.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6235   -9.9963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.9814   -9.2530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8192  -10.1799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6235   -8.5097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1742   -9.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8192   -8.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  8  2  1  1  0  0  0
  9  3  1  6  0  0  0
 10  4  1  6  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x0000560be1dc5170>

HMDB0002541
     RDKit          3D
Galactonolactone
 22 22  0  0  0  0  0  0  0  0999 V2000
    1.8707    2.0535    1.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0806    1.3241    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861    1.5244    0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2983    0.5663    1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5422   -0.1720   -0.2608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3288    0.5807   -1.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3147   -0.6025   -0.9731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6284   -1.7435   -1.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8485   -0.9267   -0.1047 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4972   -1.5308    1.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    0.2714    0.0801 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0296    0.7616   -1.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2097   -0.1425    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    1.1363    1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215   -1.0995    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    1.5323   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0069    0.1850   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7290   -2.4895   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763   -1.6914   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -1.1830    1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6848   -0.0115    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    1.6572   -1.3312 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
  9 11  1  0
 11 12  1  0
 11  2  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  1
  6 16  1  0
  7 17  1  6
  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:0x0000560be1dc5170>


  Mrv0541 02231219332D          

 12 12  0  0  1  0            999 V2000
   20.1379  -10.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8064   -9.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6357  -10.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1379   -7.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1742   -8.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6357   -7.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6235   -9.9963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.9814   -9.2530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8192  -10.1799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6235   -8.5097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1742   -9.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8192   -8.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  8  2  1  1  0  0  0
  9  3  1  6  0  0  0
 10  4  1  6  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030372

> <DATABASE_NAME>
MIME

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

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

> <INCHI_KEY>
WTXGYGWMPUGBAL-MGCNEYSASA-N

> <FORMULA>
C6H10O6

> <MOLECULAR_WEIGHT>
178.14

> <EXACT_MASS>
178.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
14.98612077352411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one

> <ALOGPS_LOGP>
-2.29

> <JCHEM_LOGP>
-2.745273186

> <ALOGPS_LOGS>
0.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.906875629542832

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.613432379830346

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5331414100681213

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
34.7788

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galactonolactone

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x0000560be1dc5170>

HMDB0002541
     RDKit          3D
Galactonolactone
 22 22  0  0  0  0  0  0  0  0999 V2000
    1.8707    2.0535    1.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0806    1.3241    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861    1.5244    0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2983    0.5663    1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5422   -0.1720   -0.2608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3288    0.5807   -1.1346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3147   -0.6025   -0.9731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6284   -1.7435   -1.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8485   -0.9267   -0.1047 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4972   -1.5308    1.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    0.2714    0.0801 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0296    0.7616   -1.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2097   -0.1425    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    1.1363    1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215   -1.0995    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    1.5323   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0069    0.1850   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7290   -2.4895   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763   -1.6914   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -1.1830    1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6848   -0.0115    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    1.6572   -1.3312 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
  9 11  1  0
 11 12  1  0
 11  2  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  1
  6 16  1  0
  7 17  1  6
  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:0x0000560be1dc5170>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      37.591 -19.864   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      38.839 -17.272   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.787 -20.504   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      37.591 -14.681   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      33.925 -16.502   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      34.787 -14.041   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      36.631 -18.660   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      37.299 -17.272   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.129 -19.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.631 -15.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.925 -18.042   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.129 -15.542   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5   11   12                                                       
CONECT    6   12                                                            
CONECT    7    1    8    9                                                  
CONECT    8    2    7   10                                                  
CONECT    9    3    7   11                                                  
CONECT   10    4    8   12                                                  
CONECT   11    5    9                                                       
CONECT   12    5    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for #<Metabolite:0x0000560be1dc5170>

COMPND    HMDB0002541
HETATM    1  O1  UNL     1       1.871   2.054   1.523  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.081   1.324   0.884  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.286   1.524   0.955  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.298   0.566   1.025  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.542  -0.172  -0.261  1.00  0.00           C  
HETATM    6  O3  UNL     1      -2.329   0.581  -1.135  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.315  -0.603  -0.973  1.00  0.00           C  
HETATM    8  O4  UNL     1      -0.628  -1.743  -1.728  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.849  -0.927  -0.105  1.00  0.00           C  
HETATM   10  O5  UNL     1       0.497  -1.531   1.094  1.00  0.00           O  
HETATM   11  C6  UNL     1       1.746   0.271   0.080  1.00  0.00           C  
HETATM   12  O6  UNL     1       2.030   0.762  -1.204  1.00  0.00           O  
HETATM   13  H1  UNL     1      -1.210  -0.142   1.877  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.252   1.136   1.244  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.122  -1.099   0.008  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.094   1.532  -0.982  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.007   0.185  -1.714  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.729  -2.489  -1.082  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.476  -1.691  -0.651  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.974  -1.183   1.876  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.685  -0.011   0.599  1.00  0.00           H  
HETATM   22  H10 UNL     1       1.603   1.657  -1.331  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4
CONECT    4    5   13   14
CONECT    5    6    7   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:0x0000560be1dc5170>

O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O
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INCHI for #<Metabolite:0x0000560be1dc5170>

InChI=1S/C6H10O6/c7-2-1-12-6(11)5(10)4(9)3(2)8/h2-5,7-10H,1H2/t2-,3+,4+,5-/m1/s1
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Synonyms
ValueSource
Galactonolactone, (D)-isomerMeSH
Galactonolactone, (L)-isomerMeSH
D-galactono-1,4-LactoneHMDB
D-galactono-1,5-LactoneHMDB
D-galactono-8-LactoneHMDB
D-GalactonolactoneHMDB
delta-galactono-1,4-LactoneHMDB
delta-galactono-1,5-LactoneHMDB
delta-galactono-8-LactoneHMDB
delta-GalactonolactoneHMDB
gamma-D-GalactonolactoneHMDB
gamma-delta-GalactonolactoneHMDB
GalactonolactoneMeSH
Molecular FormulaC6H10O6
Average Mass178.14
Monoisotopic Mass178.047738052
IUPAC Name(3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one
Traditional Namegalactonolactone
CAS Registry Number2426-46-2
SMILES
O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C6H10O6/c7-2-1-12-6(11)5(10)4(9)3(2)8/h2-5,7-10H,1H2/t2-,3+,4+,5-/m1/s1
InChI KeyWTXGYGWMPUGBAL-MGCNEYSASA-N