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Showing NP-Card for Galactonolactone (NP0086988)

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Record Information
Version2.0
Created at2022-05-11 16:36:36 UTC
Updated at2022-05-11 16:36:37 UTC
NP-MRD IDNP0086988
Secondary Accession NumbersNone
Natural Product Identification
Common NameGalactonolactone
DescriptionGalactonolactone belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Galactonolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Galactonolactone was first documented in 1991 (PMID: 1797843). Galactonolactone exists in all living organisms, ranging from bacteria to humans.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086988 (Galactonolactone)


  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 NP0086988 (Galactonolactone)

     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    2.3660   -1.9522   -1.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4374   -1.2342   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1432   -1.7267   -0.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1024   -1.1107   -0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5158   -0.2313    0.1727 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9977   -1.0567    1.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    0.6572    0.7328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1173    1.8480    1.1589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    1.0398   -0.1628 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2804    1.1827   -1.4916 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046    0.0744   -0.0767 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2632   -0.0803    1.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -0.5883   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606   -1.9460   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079    0.3534   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0880   -1.9855    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529    0.2193    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    1.6893    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274    2.0377    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    1.6923   -1.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.5070   -0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9774    0.6108    1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  0
  9  7  1  0
  7  8  1  0
  7  5  1  0
  6 16  1  0
  5 15  1  6
  4 13  1  0
  4 14  1  0
 11 21  1  6
 12 22  1  0
  9 19  1  1
 10 20  1  0
  7 17  1  1
  8 18  1  0
M  END
Download

3D SDF for NP0086988 (Galactonolactone)


  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>
NP0086988

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0086988 (Galactonolactone)

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PDB for NP0086988 (Galactonolactone)
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 NP0086988 (Galactonolactone)
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SMILES for NP0086988 (Galactonolactone)
O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O
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INCHI for NP0086988 (Galactonolactone)
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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View in JSmol
Synonyms
ValueSource
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
Galactonolactone, (L)-isomerHMDB
Galactonolactone, (D)-isomerHMDB
GalactonolactoneMeSH
Chemical FormulaC6H10O6
Average Mass178.1400 Da
Monoisotopic Mass178.04774 Da
IUPAC Name(3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one
Traditional Namegalactonolactone
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 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 NMR1H NMR Spectrum (1D, 1000 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 NMR1H NMR Spectrum (1D, 200 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 NMR1H NMR Spectrum (1D, 300 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 NMR1H NMR Spectrum (1D, 400 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 NMR1H NMR Spectrum (1D, 500 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 NMR1H NMR Spectrum (1D, 600 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 NMR1H NMR Spectrum (1D, 700 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 NMR1H NMR Spectrum (1D, 800 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
1D NMR1H NMR Spectrum (1D, 900 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 lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassNot Available
Direct ParentLactones  
Alternative Parents
Substituents
  • Caprolactone
    • 

  • Oxepane
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.3ALOGPS
logP-2.7ChemAxon
logS0.51ALOGPS
pKa (Strongest Acidic)11.61ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.78 m³·mol⁻¹ChemAxon
Polarizability14.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002541  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023025  
KNApSAcK IDNot Available
Chemspider ID133098  
KEGG Compound IDC03383  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6712  
PubChem Compound151006  
PDB IDNot Available
ChEBI ID15895  
Good Scents IDNot Available
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  ]