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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:40:57 UTC

HMDB ID

HMDB0001151

Secondary Accession Numbers

HMDB01151

Metabolite Identification

Common Name

Allose

Description

Allose 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

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


  Mrv1652305271900022D          

 16 16  0  0  1  0            999 V2000
   10.6902   -7.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1027   -7.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9277   -7.2476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5152   -6.5331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6422   -6.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3567   -7.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0712   -6.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3567   -8.0726    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7692   -8.7871    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1817   -8.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6422   -8.4851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2297   -9.1996    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0547   -9.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9277   -8.0726    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1027   -8.0726    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5152   -8.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  3 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001151

> <DATABASE_NAME>
hmdb

> <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_KEY>
WQZGKKKJIJFFOK-HOWGCPQDSA-N

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.1559

> <EXACT_MASS>
180.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.266881512858344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

> <ALOGPS_LOGP>
-2.57

> <JCHEM_LOGP>
-2.932539218

> <ALOGPS_LOGS>
0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.687538461190869

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.298101552080594

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810792051782764

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
35.923399999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(D)-allose

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      19.955 -14.863   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      20.725 -13.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.265 -13.529   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      21.495 -12.195   0.000  0.00  0.00           H+0
HETATM    5  O   UNK     0      23.599 -12.759   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      24.933 -13.529   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      26.266 -12.759   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      24.933 -15.069   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      25.703 -16.403   0.000  0.00  0.00           H+0
HETATM   10  O   UNK     0      26.473 -15.069   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      23.599 -15.839   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      22.829 -17.173   0.000  0.00  0.00           H+0
HETATM   13  O   UNK     0      24.369 -17.173   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      22.265 -15.069   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      20.725 -15.069   0.000  0.00  0.00           H+0
HETATM   16  O   UNK     0      21.495 -16.403   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   14                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3   11   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
WURCS=2.0/1,1,0/[a1111h-1x_1-5]/1/	ChEBI
beta-D-Allopyranose	HMDB
beta-D-Allose	HMDB
beta-delta-Allopyranose	HMDB
beta-delta-Allose	HMDB
D-Allose	HMDB
delta-Allose	HMDB
DL-Allose	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

(3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Traditional Name

(D)-allose

CAS Registry Number

6038-51-3

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 Key

WQZGKKKJIJFFOK-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

allopyranose (CHEBI:37741 )
L-allose (CHEBI:37741 )

Ontology

Not Available

Urine (PMID: 28157703)

Cellular substructure

Cytoplasm (HMDB: HMDB0001151)

Source

Endogenous

Endogenous (HMDB: HMDB0001151)

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Lagomorph

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Anatidae (FooDB: FOOD00576)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Rock ptarmigan (FooDB: FOOD00597)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Caprae

Domestic goat (FooDB: FOOD00529)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	128.0 - 128.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	782 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.9	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.92 m³·mol⁻¹	ChemAxon
Polarizability	16.27 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.356	31661259
DarkChem	[M-H]-	134.746	31661259
AllCCS	[M+H]+	140.814	32859911
AllCCS	[M-H]-	131.809	32859911
DeepCCS	[M+H]+	135.54	30932474
DeepCCS	[M-H]-	133.145	30932474
DeepCCS	[M-2H]-	166.952	30932474
DeepCCS	[M+Na]+	142.496	30932474
AllCCS	[M+H]+	140.8	32859911
AllCCS	[M+H-H2O]+	136.7	32859911
AllCCS	[M+NH4]+	144.7	32859911
AllCCS	[M+Na]+	145.8	32859911
AllCCS	[M-H]-	131.8	32859911
AllCCS	[M+Na-2H]-	132.8	32859911
AllCCS	[M+HCOO]-	134.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allose	[H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O	3485.8	Standard polar	33892256
Allose	[H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O	1813.3	Standard non polar	33892256
Allose	[H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O	1593.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Allose,1TMS,isomer #1	C[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O	1741.6	Semi standard non polar	33892256
Allose,1TMS,isomer #2	C[Si](C)(C)OC1O[C@@H](CO)[C@H](O)[C@H](O)[C@@H]1O	1730.0	Semi standard non polar	33892256
Allose,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1C(O)O[C@@H](CO)[C@H](O)[C@@H]1O	1732.5	Semi standard non polar	33892256
Allose,1TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)C(O)O[C@@H](CO)[C@@H]1O	1719.7	Semi standard non polar	33892256
Allose,1TMS,isomer #5	C[Si](C)(C)O[C@H]1[C@H](CO)OC(O)[C@@H](O)[C@H]1O	1712.9	Semi standard non polar	33892256
Allose,2TMS,isomer #1	C[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C)[C@@H](O)[C@@H](O)[C@H]1O	1742.5	Semi standard non polar	33892256
Allose,2TMS,isomer #10	C[Si](C)(C)O[C@H]1[C@H](CO)OC(O)[C@@H](O)[C@H]1O[Si](C)(C)C	1696.7	Semi standard non polar	33892256
Allose,2TMS,isomer #2	C[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O	1759.7	Semi standard non polar	33892256
Allose,2TMS,isomer #3	C[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O	1747.2	Semi standard non polar	33892256
Allose,2TMS,isomer #4	C[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C	1719.4	Semi standard non polar	33892256
Allose,2TMS,isomer #5	C[Si](C)(C)OC1O[C@@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O	1734.2	Semi standard non polar	33892256
Allose,2TMS,isomer #6	C[Si](C)(C)OC1O[C@@H](CO)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O	1719.1	Semi standard non polar	33892256
Allose,2TMS,isomer #7	C[Si](C)(C)OC1O[C@@H](CO)[C@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C	1727.4	Semi standard non polar	33892256
Allose,2TMS,isomer #8	C[Si](C)(C)O[C@@H]1C(O)O[C@@H](CO)[C@H](O[Si](C)(C)C)[C@@H]1O	1732.0	Semi standard non polar	33892256
Allose,2TMS,isomer #9	C[Si](C)(C)O[C@@H]1C(O)O[C@@H](CO)[C@H](O)[C@@H]1O[Si](C)(C)C	1714.1	Semi standard non polar	33892256
Allose,3TMS,isomer #1	C[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O	1736.6	Semi standard non polar	33892256
Allose,3TMS,isomer #10	C[Si](C)(C)O[C@@H]1C(O)O[C@@H](CO)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1739.1	Semi standard non polar	33892256
Allose,3TMS,isomer #2	C[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O	1760.0	Semi standard non polar	33892256
Allose,3TMS,isomer #3	C[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C)[C@@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C	1733.8	Semi standard non polar	33892256
Allose,3TMS,isomer #4	C[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	1755.0	Semi standard non polar	33892256
Allose,3TMS,isomer #5	C[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	1761.4	Semi standard non polar	33892256
Allose,3TMS,isomer #6	C[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1712.5	Semi standard non polar	33892256
Allose,3TMS,isomer #7	C[Si](C)(C)OC1O[C@@H](CO)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O	1743.0	Semi standard non polar	33892256
Allose,3TMS,isomer #8	C[Si](C)(C)OC1O[C@@H](CO)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C	1758.0	Semi standard non polar	33892256
Allose,3TMS,isomer #9	C[Si](C)(C)OC1O[C@@H](CO)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1751.2	Semi standard non polar	33892256
Allose,4TMS,isomer #1	C[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	1835.0	Semi standard non polar	33892256
Allose,4TMS,isomer #2	C[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	1846.5	Semi standard non polar	33892256
Allose,4TMS,isomer #3	C[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1821.2	Semi standard non polar	33892256
Allose,4TMS,isomer #4	C[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1823.7	Semi standard non polar	33892256
Allose,4TMS,isomer #5	C[Si](C)(C)OC1O[C@@H](CO)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1805.3	Semi standard non polar	33892256
Allose,5TMS,isomer #1	C[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1901.5	Semi standard non polar	33892256
Allose,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O	2009.7	Semi standard non polar	33892256
Allose,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1O[C@@H](CO)[C@H](O)[C@H](O)[C@@H]1O	1972.1	Semi standard non polar	33892256
Allose,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C(O)O[C@@H](CO)[C@H](O)[C@@H]1O	1977.9	Semi standard non polar	33892256
Allose,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)C(O)O[C@@H](CO)[C@@H]1O	1970.2	Semi standard non polar	33892256
Allose,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](CO)OC(O)[C@@H](O)[C@H]1O	1963.2	Semi standard non polar	33892256
Allose,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)[C@H]1O	2210.8	Semi standard non polar	33892256
Allose,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](CO)OC(O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2187.0	Semi standard non polar	33892256
Allose,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	2229.0	Semi standard non polar	33892256
Allose,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2219.6	Semi standard non polar	33892256
Allose,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2194.3	Semi standard non polar	33892256
Allose,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1O[C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O	2214.2	Semi standard non polar	33892256
Allose,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1O[C@@H](CO)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2201.2	Semi standard non polar	33892256
Allose,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1O[C@@H](CO)[C@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2204.1	Semi standard non polar	33892256
Allose,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1C(O)O[C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2208.3	Semi standard non polar	33892256
Allose,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1C(O)O[C@@H](CO)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2204.8	Semi standard non polar	33892256
Allose,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	2441.5	Semi standard non polar	33892256
Allose,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1C(O)O[C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2467.6	Semi standard non polar	33892256
Allose,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2450.1	Semi standard non polar	33892256
Allose,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2440.1	Semi standard non polar	33892256
Allose,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2472.3	Semi standard non polar	33892256
Allose,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2470.8	Semi standard non polar	33892256
Allose,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2436.3	Semi standard non polar	33892256
Allose,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1O[C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2454.9	Semi standard non polar	33892256
Allose,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1O[C@@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2464.1	Semi standard non polar	33892256
Allose,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1O[C@@H](CO)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2462.8	Semi standard non polar	33892256
Allose,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2676.4	Semi standard non polar	33892256
Allose,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2680.2	Semi standard non polar	33892256
Allose,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2656.7	Semi standard non polar	33892256
Allose,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O)[C@@H](O[Si](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)C	2691.4	Semi standard non polar	33892256
Allose,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1O[C@@H](CO)[C@H](O[Si](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)C	2674.9	Semi standard non polar	33892256
Allose,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H]1OC(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](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)C	2886.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Allose GC-MS (Non-derivatized) - 70eV, Positive	splash10-08g0-9700000000-0c1d58a37be53bdad540	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allose GC-MS (5 TMS) - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allose Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-00kr-9400000000-b75d88e3b13f8251f30e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allose Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-0a4i-9000000000-b1bddab3816e1286ec8d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allose Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-0a4i-9000000000-e6f172b0f12150f5bb00	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 10V, Positive-QTOF	splash10-01q9-0900000000-865ff3c21e042be41194	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 20V, Positive-QTOF	splash10-03ea-1900000000-ff3096b7f2c9d1141b1f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 40V, Positive-QTOF	splash10-0007-9100000000-c4b6f8b4217029a276d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 10V, Negative-QTOF	splash10-004i-0900000000-01d354be667f71ed78d1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 20V, Negative-QTOF	splash10-01t9-4900000000-e4b00a8035bbe7f7a899	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 40V, Negative-QTOF	splash10-0006-9000000000-19c01224e57df3618fe5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 10V, Negative-QTOF	splash10-004i-1900000000-3a8c197f61db9f867708	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 20V, Negative-QTOF	splash10-056r-9700000000-3438a670a219e810097b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 40V, Negative-QTOF	splash10-0a4l-9000000000-1def59bcacabecde3f20	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 10V, Positive-QTOF	splash10-01qa-0900000000-c96480a7d2f58a7c42d7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 20V, Positive-QTOF	splash10-03dj-9400000000-043eb11900316cc95e58	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allose 40V, Positive-QTOF	splash10-01vn-9000000000-80dd901f98baa92e32b1	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allose

METLIN ID

348

PubChem Compound

12285879

PDB ID

Not Available

ChEBI ID

37741

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Allose (HMDB0001151)

MOL for HMDB0001151 (Allose)

3D MOL for HMDB0001151 (Allose)

3D SDF for HMDB0001151 (Allose)

3D-SDF for HMDB0001151 (Allose)

PDB for HMDB0001151 (Allose)

3D PDB for HMDB0001151 (Allose)

SMILES for HMDB0001151 (Allose)

INCHI for HMDB0001151 (Allose)

Structure for HMDB0001151 (Allose)

3D Structure for HMDB0001151 (Allose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra