Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-06-02 19:07:47 UTC
Update Date2021-10-13 05:35:02 UTC
HMDB IDHMDB0012327
Secondary Accession Numbers
  • HMDB12327
Metabolite Identification
Common Name2-Deoxygalactopyranose
Description2-Deoxygalactopyranose is an optical isomer of 2-deoxyglucose, which has the 2-hydroxyl group replaced by hydrogen. 2-deoxygalactose inhibits galactose uptake and oxidation in galactose-grown cells. Similar to galactose,. 2-deoxyglucose, and D-fucose, 2-deoxygalactose induces uptake of H+ when the sugar is added to anaerobic wild-type cells that contain the galactose transport system, whereas the maximal rate of uptake is one-half to one-third of that of galactose. 2-Deoxygalactose is a specific substrate of the galactose permease. None of the other galactose transport systems, including methyl beta-D-thiogalactosides I and II, the beta-methyl-galactoside permease, and both arabinose systems, is able to catalyze transport of 2-deoxygalactose to a significant extent. 2-Deoxygalactose can also be used to isolate mutants defective in galactose permease, since it is bacteriostatic.
Structure
Data?1582753042
Synonyms
ValueSource
2-Deoxy-D-galactoseChEBI
2-DeoxygalactoseChEBI
2-Deoxy-D-galactopyranoseHMDB
2-Deoxy-D-lyxo-hexopyranoseHMDB
alpha FucoseMeSH, HMDB
alpha-FucoseMeSH, HMDB
DeoxygalactoseMeSH, HMDB
FucoseMeSH, HMDB
Chemical FormulaC6H12O5
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
IUPAC Name(4R,5R,6R)-6-(hydroxymethyl)oxane-2,4,5-triol
Traditional Name(4R,5R,6R)-6-(hydroxymethyl)oxane-2,4,5-triol
CAS Registry Number25494-04-6
SMILES
OC[C@H]1OC(O)C[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5?,6-/m1/s1
InChI KeyPMMURAAUARKVCB-DUVQVXGLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point456.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-3.070 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility984 g/LALOGPS
logP-2.5ALOGPS
logP-2ChemAxon
logS0.78ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.41 m³·mol⁻¹ChemAxon
Polarizability15.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.0131661259
DarkChem[M-H]-130.98431661259
DeepCCS[M+H]+136.83730932474
DeepCCS[M-H]-134.58630932474
DeepCCS[M-2H]-169.35430932474
DeepCCS[M+Na]+143.6730932474
AllCCS[M+H]+136.932859911
AllCCS[M+H-H2O]+132.532859911
AllCCS[M+NH4]+141.132859911
AllCCS[M+Na]+142.332859911
AllCCS[M-H]-128.632859911
AllCCS[M+Na-2H]-129.932859911
AllCCS[M+HCOO]-131.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-DeoxygalactopyranoseOC[C@H]1OC(O)C[C@@H](O)[C@H]1O3012.0Standard polar33892256
2-DeoxygalactopyranoseOC[C@H]1OC(O)C[C@@H](O)[C@H]1O1613.0Standard non polar33892256
2-DeoxygalactopyranoseOC[C@H]1OC(O)C[C@@H](O)[C@H]1O1471.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Deoxygalactopyranose,1TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O)[C@H]1O1602.2Semi standard non polar33892256
2-Deoxygalactopyranose,1TMS,isomer #2C[Si](C)(C)OC1C[C@@H](O)[C@@H](O)[C@@H](CO)O11617.1Semi standard non polar33892256
2-Deoxygalactopyranose,1TMS,isomer #3C[Si](C)(C)O[C@@H]1CC(O)O[C@H](CO)[C@@H]1O1606.9Semi standard non polar33892256
2-Deoxygalactopyranose,1TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@H](O)CC(O)O[C@@H]1CO1594.4Semi standard non polar33892256
2-Deoxygalactopyranose,2TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O)[C@H]1O1626.8Semi standard non polar33892256
2-Deoxygalactopyranose,2TMS,isomer #2C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O[Si](C)(C)C)[C@H]1O1637.4Semi standard non polar33892256
2-Deoxygalactopyranose,2TMS,isomer #3C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O)[C@H]1O[Si](C)(C)C1607.6Semi standard non polar33892256
2-Deoxygalactopyranose,2TMS,isomer #4C[Si](C)(C)OC1C[C@@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO)O11609.3Semi standard non polar33892256
2-Deoxygalactopyranose,2TMS,isomer #5C[Si](C)(C)OC1C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO)O11643.1Semi standard non polar33892256
2-Deoxygalactopyranose,2TMS,isomer #6C[Si](C)(C)O[C@H]1[C@@H](CO)OC(O)C[C@H]1O[Si](C)(C)C1588.3Semi standard non polar33892256
2-Deoxygalactopyranose,3TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@H]1O1678.8Semi standard non polar33892256
2-Deoxygalactopyranose,3TMS,isomer #2C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O)[C@H]1O[Si](C)(C)C1692.6Semi standard non polar33892256
2-Deoxygalactopyranose,3TMS,isomer #3C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C1650.2Semi standard non polar33892256
2-Deoxygalactopyranose,3TMS,isomer #4C[Si](C)(C)OC1C[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO)O11636.4Semi standard non polar33892256
2-Deoxygalactopyranose,4TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C1717.0Semi standard non polar33892256
2-Deoxygalactopyranose,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O)[C@H]1O1853.1Semi standard non polar33892256
2-Deoxygalactopyranose,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1C[C@@H](O)[C@@H](O)[C@@H](CO)O11853.6Semi standard non polar33892256
2-Deoxygalactopyranose,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1CC(O)O[C@H](CO)[C@@H]1O1841.4Semi standard non polar33892256
2-Deoxygalactopyranose,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)CC(O)O[C@@H]1CO1841.6Semi standard non polar33892256
2-Deoxygalactopyranose,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H]1O2069.0Semi standard non polar33892256
2-Deoxygalactopyranose,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2075.2Semi standard non polar33892256
2-Deoxygalactopyranose,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2059.5Semi standard non polar33892256
2-Deoxygalactopyranose,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO)O12070.9Semi standard non polar33892256
2-Deoxygalactopyranose,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O12093.0Semi standard non polar33892256
2-Deoxygalactopyranose,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](CO)OC(O)C[C@H]1O[Si](C)(C)C(C)(C)C2057.2Semi standard non polar33892256
2-Deoxygalactopyranose,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2317.6Semi standard non polar33892256
2-Deoxygalactopyranose,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2328.1Semi standard non polar33892256
2-Deoxygalactopyranose,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2326.9Semi standard non polar33892256
2-Deoxygalactopyranose,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O12313.2Semi standard non polar33892256
2-Deoxygalactopyranose,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2556.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Deoxygalactopyranose GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-9500000000-1dd63af9d5c88579c7732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Deoxygalactopyranose GC-MS (4 TMS) - 70eV, Positivesplash10-0fbi-9457500000-3209b7e1fc11efc7490b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Deoxygalactopyranose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Deoxygalactopyranose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 10V, Positive-QTOFsplash10-014j-0900000000-0dc650a397e8c7b1d3992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 20V, Positive-QTOFsplash10-00mk-3900000000-16c36b909df5ddf5684d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 40V, Positive-QTOFsplash10-05dm-9100000000-e5a5c9e9bf3a8931c5d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 10V, Negative-QTOFsplash10-03di-1900000000-921ea67907cab90f2f8f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 20V, Negative-QTOFsplash10-08fs-7900000000-4cec920b05a3b679d1392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 40V, Negative-QTOFsplash10-0006-9000000000-b986f5de02e6eb67f3d02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 10V, Positive-QTOFsplash10-004i-0900000000-6a825258a26550998fa92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 20V, Positive-QTOFsplash10-05xs-9700000000-e7f7cadc097fcc73f1012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 40V, Positive-QTOFsplash10-052b-9000000000-6f4d5566a761ecc054412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 10V, Negative-QTOFsplash10-03di-4900000000-5a1e28bf26404acffb6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 20V, Negative-QTOFsplash10-0a4l-9100000000-f9298acb4c73165917192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Deoxygalactopyranose 40V, Negative-QTOFsplash10-0006-9000000000-77c0ac008b492684928d2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028946
KNApSAcK IDC00052630
Chemspider ID388857
KEGG Compound IDC02781
BioCyc IDCPD-5861
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439804
PDB IDNot Available
ChEBI ID90759
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1175011
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mao YY, Bai JQ, Chen JH, Shou ZF, He Q, Wu JY, Chen Y, Cheng YY: A pilot study of GC/MS-based serum metabolic profiling of acute rejection in renal transplantation. Transpl Immunol. 2008 Apr;19(1):74-80. doi: 10.1016/j.trim.2008.01.006. Epub 2008 Feb 22. [PubMed:18346641 ]
  2. Postma PW, Keizer HG, Koolwijk P: Transport of trehalose in Salmonella typhimurium. J Bacteriol. 1986 Dec;168(3):1107-11. [PubMed:3023298 ]
  3. Thienen GM, Postma PW, Dam KV: Proton movements coupled to sugar transport via the galactose transport system in Salmonella typhimurium. Eur J Biochem. 1977 Mar 1;73(2):521-7. [PubMed:14832 ]