MiMeDB: Showing metabocard for Galactonolactone (MMDBc0030372)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:05:41 UTC

Update Date

2024-04-30 19:46:07 UTC

Metabolite ID

MMDBc0030372

Metabolite Identification

Common Name

Galactonolactone

Description

Galactonolactone 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

Synonyms

Value	Source
Galactonolactone, (D)-isomer	MeSH
Galactonolactone, (L)-isomer	MeSH
D-galactono-1,4-Lactone	HMDB
D-galactono-1,5-Lactone	HMDB
D-galactono-8-Lactone	HMDB
D-Galactonolactone	HMDB
delta-galactono-1,4-Lactone	HMDB
delta-galactono-1,5-Lactone	HMDB
delta-galactono-8-Lactone	HMDB
delta-Galactonolactone	HMDB
gamma-D-Galactonolactone	HMDB
gamma-delta-Galactonolactone	HMDB
Galactonolactone	MeSH

Molecular Formula

C₆H₁₀O₆

Average Mass

178.14

Monoisotopic Mass

178.047738052

IUPAC Name

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

Traditional Name

galactonolactone

CAS Registry Number

2426-46-2

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 Key

WTXGYGWMPUGBAL-MGCNEYSASA-N

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Not Available

Direct Parent

Lactones

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	583 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.7	ChemAxon
logS	0.51	ALOGPS
pKa (Strongest Acidic)	11.61	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.78 m³·mol⁻¹	ChemAxon
Polarizability	14.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06rl-9400000000-9e4502053b3fe09f123e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0kou-3279300000-1418a34fa3efbbb205d1	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0900000000-685a5dbb4f8a7102dcc5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-2900000000-83611a0f9b640623ac24	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9200000000-fbfa10412acfeb6c4811	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-61baef021fc455ee67ea	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-2900000000-9c6963bd735f92051d97	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-4f71f72cc2972d6c238b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-4af21996c208dcba14ab	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fu-9500000000-ac5d2741d49de16a664a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btc-9000000000-0a9b1531d89f4242cbcb	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-9622261df6835436c4f0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abc-9200000000-3d5e0ea9ad8151fc6cc0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-8c8e168512fbb0f52fa3	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0002541

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023025

KNApSAcK ID

Not Available

Chemspider ID

133098

KEGG Compound ID

C03383

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6712

PubChem Compound

151006

PDB ID

Not Available

ChEBI ID

15895

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Gates SC, Sweeley CC, Krivit W, DeWitt D, Blaisdell BE: Automated metabolic profiling of organic acids in human urine. II. Analysis of urine samples from "healthy" adults, sick children, and children with neuroblastoma. Clin Chem. 1978 Oct;24(10):1680-9. [PubMed:699273 ]
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. doi: 10.1016/0378-4347(91)80530-p. [PubMed:1797843 ]

Showing metabocard for Galactonolactone (MMDBc0030372)

MOL for #<Metabolite:0x00007f46e001ec48>

3D MOL for #<Metabolite:0x00007f46e001ec48>

3D SDF for #<Metabolite:0x00007f46e001ec48>

3D-SDF for #<Metabolite:0x00007f46e001ec48>

PDB for #<Metabolite:0x00007f46e001ec48>

3D PDB for #<Metabolite:0x00007f46e001ec48>

SMILES for #<Metabolite:0x00007f46e001ec48>

INCHI for #<Metabolite:0x00007f46e001ec48>

Structure for #<Metabolite:0x00007f46e001ec48>

3D Structure for #<Metabolite:0x00007f46e001ec48>