Allose (CHEM035094)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:29:05 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035094
Identification
Common NameAllose
ClassSmall Molecule
DescriptionThe L-enantiomer of allopyranose.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
WURCS=2.0/1,1,0/[a1111h-1x_1-5]/1/ChEBI
beta-D-AllopyranoseHMDB
beta-D-AlloseHMDB
beta-delta-AllopyranoseHMDB
beta-delta-AlloseHMDB
D-AlloseHMDB
delta-AlloseHMDB
DL-AlloseHMDB
Chemical FormulaC6H12O6
Average Molecular Mass180.156 g/mol
Monoisotopic Mass180.063 g/mol
CAS Registry Number6038-51-3
IUPAC Name(3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Name(D)-allose
SMILES[H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O
InChI IdentifierInChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6?/m0/s1
InChI KeyWQZGKKKJIJFFOK-HOWGCPQDSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility782 g/LALOGPS
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.27 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08g0-9700000000-0c1d58a37be53bdad540Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00kr-9400000000-b75d88e3b13f8251f30eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9000000000-b1bddab3816e1286ec8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-9000000000-e6f172b0f12150f5bb00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-865ff3c21e042be41194Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-1900000000-ff3096b7f2c9d1141b1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-c4b6f8b4217029a276d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-01d354be667f71ed78d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-4900000000-e4b00a8035bbe7f7a899Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-19c01224e57df3618fe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-3a8c197f61db9f867708Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9700000000-3438a670a219e810097bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-1def59bcacabecde3f20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0900000000-c96480a7d2f58a7c42d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-9400000000-043eb11900316cc95e58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vn-9000000000-80dd901f98baa92e32b1Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001151
FooDB IDFDB022453
Phenol Explorer IDNot Available
KNApSAcK IDC00052802
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID348
PDB IDNot Available
Wikipedia LinkAllose
Chemspider ID13076841
ChEBI ID37741
PubChem Compound ID12285879
Kegg Compound IDC01487
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Menavuvu Buetusiwa Thomas; Poonperm Wayoon; Leang Khim; Noguchi Naoki; Okada Hiromi; Morimoto Kenji; Granstrom Tom Birger; Takada Goro; Izumori Ken Efficient biosynthesis of D-allose from D-psicose by cross-linked recombinant L-rhamnose isomerase: separation of product by ethanol crystallization. Journal of bioscience and bioengineering (2006), 101(4), 340-5.
2. Menavuvu Buetusiwa Thomas; Poonperm Wayoon; Leang Khim; Noguchi Naoki; Okada Hiromi; Morimoto Kenji; Granstrom Tom Birger; Takada Goro; Izumori Ken Efficient biosynthesis of D-allose from D-psicose by cross-linked recombinant L-rhamnose isomerase: separation of product by ethanol crystallization. Journal of bioscience and bioengineering (2006), 101(4), 340-5.
3. Sui L, Dong Y, Watanabe Y, Yamaguchi F, Hatano N, Izumori K, Tokuda M: Growth inhibitory effect of D-allose on human ovarian carcinoma cells in vitro. Anticancer Res. 2005 Jul-Aug;25(4):2639-44.
4. Sui L, Dong Y, Watanabe Y, Yamaguchi F, Hatano N, Tsukamoto I, Izumori K, Tokuda M: The inhibitory effect and possible mechanisms of D-allose on cancer cell proliferation. Int J Oncol. 2005 Oct;27(4):907-12.
5. Hossain MA, Izuishi K, Maeta H: Protective effects of D-allose against ischemia reperfusion injury of the rat liver. J Hepatobiliary Pancreat Surg. 2003;10(3):218-25.
6. Hossain MA, Wakabayashi H, Izuishi K, Okano K, Yachida S, Tokuda M, Izumori K, Maeta H: Improved microcirculatory effect of D-allose on hepatic ischemia reperfusion following partial hepatectomy in cirrhotic rat liver. J Biosci Bioeng. 2006 Apr;101(4):369-71.
7. Hossain MA, Wakabayashi H, Goda F, Kobayashi S, Maeba T, Maeta H: Effect of the immunosuppressants FK506 and D-allose on allogenic orthotopic liver transplantation in rats. Transplant Proc. 2000 Nov;32(7):2021-3.
8. Hirooka K, Miyamoto O, Jinming P, Du Y, Itano T, Baba T, Tokuda M, Shiraga F: Neuroprotective effects of D-allose against retinal ischemia-reperfusion injury. Invest Ophthalmol Vis Sci. 2006 Apr;47(4):1653-7.
9. Kimura S, Zhang GX, Nishiyama A, Nagai Y, Nakagawa T, Miyanaka H, Fujisawa Y, Miyatake A, Nagai T, Tokuda M, Abe Y: D-allose, an all-cis aldo-hexose, suppresses development of salt-induced hypertension in Dahl rats. J Hypertens. 2005 Oct;23(10):1887-94.