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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:54 UTC
NP-MRD IDNP0000450
Secondary Accession NumbersNone
Natural Product Identification
Common NameAllose
DescriptionAllose is an aldohexose sugar. Allose is a C-3 epimer of glucose. D-allose is a rare sugar found in nature and, because of its very limited amount and of the high cost associated with its synthesis, its physiological functions remain virtually unknown (PMID 16080505 ). It is believed to have inhibitory effect on cancer cell proliferation (PMID 16142305 ), protective effects against ischemia reperfusion injury (PMID 14605979 , 16716947 ), immunosuppressant on allogenic orthotopic liver transplantation (PMID 11120048 ), neuroprotective effects against retinal ischemia (PMID 16565406 ), suppress development of salt-induced hypertension (PMID 16148613 ) and an inhibitory effect on human ovarian carcinoma cells (PMID 16080505 ). It is a rare monosaccharide that has been isolated from the leaves of the African shrub Protea rubropilosa. It is soluble in water and practically insoluble in methanol.
Structure
Thumb
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 Mass180.1559 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Name(D)-allose
CAS Registry Number6038-51-3
SMILES
[H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O
InChI Identifier
InChI=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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Averrhoa carambolaKNApSAcK Database
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 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point128.0 - 128.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001151
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022453
KNApSAcK IDC00052802
Chemspider ID13076841
KEGG Compound IDC01487
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllose
METLIN ID348
PubChem Compound12285879
PDB IDNot Available
ChEBI ID37741
Good Scents IDNot Available
References
General References
  1. 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. [PubMed:16080505 ]
  2. 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. [PubMed:16142305 ]
  3. 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. [PubMed:14605979 ]
  4. 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. [PubMed:16716947 ]
  5. 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. [PubMed:11120048 ]
  6. 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. [PubMed:16565406 ]
  7. 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. [PubMed:16148613 ]