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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:09 UTC

HMDB ID

HMDB0001266

Secondary Accession Numbers

HMDB01266

Metabolite Identification

Common Name

L-Sorbose

Description

L-Sorbose, also known as L-sorbinose or L-xylo-hexulose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. L-Sorbose exists in all living species, ranging from bacteria to humans. The commercial production of vitamin C (ascorbic acid) often begins with sorbose. L-Sorbose (CAS: 87-79-6) is a ketose belonging to the group of sugars known as monosaccharides. Sorbose has been found to be a metabolite of Ketogulonicigenium (PMID:15785002 ).

Structure

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

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      28.955 -12.604   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      27.554 -13.696   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.061 -13.007   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.415 -11.449   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      24.727 -12.237   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.393 -13.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.393 -14.547   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      22.060 -15.317   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      24.727 -15.317   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.727 -16.857   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      26.061 -14.547   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      27.394 -15.317   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    3    9   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-L-Sorbopyranose	HMDB
Hex-2-ulose	HMDB
L(-) Sorbose for biochemistry	HMDB
L(-)-Sorbose	HMDB
L-(-)-Sorbose	HMDB
L-(-)-Sorbose 99%	HMDB
L-1,3,4,5,6-Pentahydroxyhexan-2-one	HMDB
L-Sorbinose	HMDB
L-Xylo-2-hexulose	HMDB
L-Xylo-hexulose	HMDB
Sorbin	HMDB
Sorbinose	HMDB
Sorbose	HMDB
Xylo-hexulose	HMDB
alpha-L-Xylo-hexopyranos-2-ulose	HMDB
Α-L-xylo-hexopyranos-2-ulose	HMDB
Α-L-sorbopyranose	HMDB
a-L-Sorbopyranose	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

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

Traditional Name

α-L-sorbopyranose

CAS Registry Number

470-15-5

SMILES

OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1

InChI Key

LKDRXBCSQODPBY-BGPJRJDNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-sorbopyranose (CHEBI:10295 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	360 mg/mL at 17 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1190 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.8	ChemAxon
logS	0.82	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	-3.5	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	36.36 m³·mol⁻¹	ChemAxon
Polarizability	16.05 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]+	140.555	31661259
DarkChem	[M-H]-	134.47	31661259
AllCCS	[M+H]+	140.433	32859911
AllCCS	[M-H]-	131.724	32859911
DeepCCS	[M+H]+	137.902	30932474
DeepCCS	[M-H]-	135.628	30932474
DeepCCS	[M-2H]-	170.123	30932474
DeepCCS	[M+Na]+	144.317	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.2	32859911
AllCCS	[M+NH4]+	144.4	32859911
AllCCS	[M+Na]+	145.6	32859911
AllCCS	[M-H]-	131.7	32859911
AllCCS	[M+Na-2H]-	132.7	32859911
AllCCS	[M+HCOO]-	133.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Sorbose	OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O	3403.1	Standard polar	33892256
L-Sorbose	OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O	1861.1	Standard non polar	33892256
L-Sorbose	OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O	1643.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Sorbose,1TMS,isomer #1	C[Si](C)(C)OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O	1753.0	Semi standard non polar	33892256
L-Sorbose,1TMS,isomer #2	C[Si](C)(C)O[C@]1(CO)OC[C@H](O)[C@@H](O)[C@@H]1O	1742.4	Semi standard non polar	33892256
L-Sorbose,1TMS,isomer #3	C[Si](C)(C)O[C@H]1CO[C@](O)(CO)[C@@H](O)[C@@H]1O	1751.6	Semi standard non polar	33892256
L-Sorbose,1TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](O)CO[C@](O)(CO)[C@H]1O	1737.4	Semi standard non polar	33892256
L-Sorbose,1TMS,isomer #5	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)CO[C@]1(O)CO	1753.5	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #1	C[Si](C)(C)OC[C@@]1(O[Si](C)(C)C)OC[C@H](O)[C@@H](O)[C@@H]1O	1727.3	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #10	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](O)CO[C@]1(O)CO	1704.1	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #2	C[Si](C)(C)OC[C@@]1(O)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	1731.9	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #3	C[Si](C)(C)OC[C@@]1(O)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	1737.4	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #4	C[Si](C)(C)OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	1727.9	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #5	C[Si](C)(C)O[C@H]1CO[C@@](CO)(O[Si](C)(C)C)[C@@H](O)[C@@H]1O	1744.2	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](O)CO[C@@](CO)(O[Si](C)(C)C)[C@H]1O	1734.5	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #7	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)CO[C@@]1(CO)O[Si](C)(C)C	1733.8	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #8	C[Si](C)(C)O[C@H]1CO[C@](O)(CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	1723.2	Semi standard non polar	33892256
L-Sorbose,2TMS,isomer #9	C[Si](C)(C)O[C@H]1CO[C@](O)(CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	1689.0	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #1	C[Si](C)(C)OC[C@@]1(O[Si](C)(C)C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	1750.3	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #10	C[Si](C)(C)O[C@H]1CO[C@](O)(CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1698.2	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #2	C[Si](C)(C)OC[C@@]1(O[Si](C)(C)C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	1767.8	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #3	C[Si](C)(C)OC[C@@]1(O[Si](C)(C)C)OC[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	1738.1	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #4	C[Si](C)(C)OC[C@@]1(O)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1713.8	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #5	C[Si](C)(C)OC[C@@]1(O)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1747.4	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #6	C[Si](C)(C)OC[C@@]1(O)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1743.9	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #7	C[Si](C)(C)O[C@H]1CO[C@@](CO)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1741.2	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #8	C[Si](C)(C)O[C@H]1CO[C@@](CO)(O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1733.3	Semi standard non polar	33892256
L-Sorbose,3TMS,isomer #9	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](O)CO[C@@]1(CO)O[Si](C)(C)C	1754.2	Semi standard non polar	33892256
L-Sorbose,4TMS,isomer #1	C[Si](C)(C)OC[C@@]1(O[Si](C)(C)C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1780.3	Semi standard non polar	33892256
L-Sorbose,4TMS,isomer #2	C[Si](C)(C)OC[C@@]1(O[Si](C)(C)C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1789.0	Semi standard non polar	33892256
L-Sorbose,4TMS,isomer #3	C[Si](C)(C)OC[C@@]1(O[Si](C)(C)C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1828.2	Semi standard non polar	33892256
L-Sorbose,4TMS,isomer #4	C[Si](C)(C)OC[C@@]1(O)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1767.7	Semi standard non polar	33892256
L-Sorbose,4TMS,isomer #5	C[Si](C)(C)O[C@H]1CO[C@@](CO)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1784.8	Semi standard non polar	33892256
L-Sorbose,5TMS,isomer #1	C[Si](C)(C)OC[C@@]1(O[Si](C)(C)C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1903.7	Semi standard non polar	33892256
L-Sorbose,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O	2006.5	Semi standard non polar	33892256
L-Sorbose,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@]1(CO)OC[C@H](O)[C@@H](O)[C@@H]1O	2009.8	Semi standard non polar	33892256
L-Sorbose,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@](O)(CO)[C@@H](O)[C@@H]1O	1988.6	Semi standard non polar	33892256
L-Sorbose,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)CO[C@](O)(CO)[C@H]1O	1962.2	Semi standard non polar	33892256
L-Sorbose,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)CO[C@]1(O)CO	1973.6	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@]1(O[Si](C)(C)C(C)(C)C)OC[C@H](O)[C@@H](O)[C@@H]1O	2193.5	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO[C@]1(O)CO	2159.5	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@]1(O)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2199.5	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@]1(O)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2185.6	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2185.4	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@@](CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2204.7	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)CO[C@@](CO)(O[Si](C)(C)C(C)(C)C)[C@H]1O	2186.0	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O)CO[C@@]1(CO)O[Si](C)(C)C(C)(C)C	2181.9	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@](O)(CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2176.1	Semi standard non polar	33892256
L-Sorbose,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@](O)(CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2151.5	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@]1(O[Si](C)(C)C(C)(C)C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2432.5	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@](O)(CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2409.5	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@]1(O[Si](C)(C)C(C)(C)C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2427.2	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@]1(O[Si](C)(C)C(C)(C)C)OC[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2413.2	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@]1(O)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2419.6	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@]1(O)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2436.8	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@@]1(O)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2430.6	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@@](CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2421.9	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@@](CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2431.1	Semi standard non polar	33892256
L-Sorbose,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO[C@@]1(CO)O[Si](C)(C)C(C)(C)C	2428.3	Semi standard non polar	33892256
L-Sorbose,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@]1(O[Si](C)(C)C(C)(C)C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2666.8	Semi standard non polar	33892256
L-Sorbose,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@]1(O[Si](C)(C)C(C)(C)C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2650.9	Semi standard non polar	33892256
L-Sorbose,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@]1(O[Si](C)(C)C(C)(C)C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2647.8	Semi standard non polar	33892256
L-Sorbose,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@]1(O)OC[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	2658.4	Semi standard non polar	33892256
L-Sorbose,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@@](CO)(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	2658.9	Semi standard non polar	33892256
L-Sorbose,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@]1(O[Si](C)(C)C(C)(C)C)OC[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	2869.0	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 - L-Sorbose GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-9700000000-3e5e0a3aa6c676c97701	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Sorbose GC-MS (5 TMS) - 70eV, Positive	splash10-004i-8422790000-fda815da7846441c6ea7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Sorbose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Sorbose 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 - L-Sorbose Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0002-0900000000-ad56c2283c4948268668	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Sorbose Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00ri-9600000000-f53f9ae5db12b8c07611	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Sorbose Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0079-9200000000-c3dabd4edd0fd062cfd4	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 10V, Positive-QTOF	splash10-01q9-0900000000-014681a0ceccca243630	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 20V, Positive-QTOF	splash10-03e9-2900000000-fdd4f1c2b01b7cd4a621	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 40V, Positive-QTOF	splash10-0c30-9200000000-a3afc1e71049f23145b0	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 10V, Negative-QTOF	splash10-00fu-9700000000-86b1b9f75df959e2158f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 20V, Negative-QTOF	splash10-024i-9800000000-1acd95dd1e6f8744308f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 40V, Negative-QTOF	splash10-0006-9000000000-545f59c3707e4298b57c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 10V, Positive-QTOF	splash10-01pk-0900000000-d9de28ed437f1079125e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 20V, Positive-QTOF	splash10-03e9-9700000000-21b6c695fb9bdd5ae08d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 40V, Positive-QTOF	splash10-0007-9000000000-7c49e3a2d60cfed68a76	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 10V, Negative-QTOF	splash10-004i-6900000000-def874fe6470032fdd27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 20V, Negative-QTOF	splash10-056r-9100000000-b495c0f16251b5ee98e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Sorbose 40V, Negative-QTOF	splash10-0a4l-9000000000-d526231c78d5ea2b9be5	2021-09-22	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
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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

Biospecimen Locations

Feces
Sweat
Urine

Tissue Locations

Adipose Tissue
Fibroblasts
Intestine
Kidney
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	0.5 (0.0-1.0) umol/mmol creatinine	Adult (>18 years old)	Both	Prostate Cancer	19212411	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Prostate cancer
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

Associated OMIM IDs

114500 (Colorectal cancer)
176807 (Prostate cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

VMH ID

SRB_L

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Banjopnoppakun, Tanaphat; Moonmangmee, Somporn; Moonmangmee, Duangtip. Production of L-sorbose by thermotolerant acetic acid bacteria. Proceeding of the Kasetsart University Annual Conference, 44th, Bangkok, Thailand, Jan. 30-Feb. 2, 2006 (2006), 117-123.

Material Safety Data Sheet (MSDS)

Not Available

General References

Gryz EA, Galicka-Latala D, Szczudlik A, Sieradzki J: [Etiopathogenesis of diabetic neuropathy]. Przegl Lek. 2000;57(12):727-31. [PubMed:11398597 ]
Nakamura J, Koh N, Sakakibara F, Hamada Y, Wakao T, Sasaki H, Mori K, Nakashima E, Naruse K, Hotta N: Diabetic neuropathy in sucrose-fed Otsuka Long-Evans Tokushima fatty rats: effect of an aldose reductase inhibitor, TAT. Life Sci. 1997;60(21):1847-57. [PubMed:9154994 ]
Wang C, So SY, Wong KK, So WW, Chan SY: Chronic sinopulmonary disease in Chinese patients with obstructive azoospermia. J Androl. 1987 Jul-Aug;8(4):225-9. [PubMed:3624059 ]
Kossi J, Peltonen J, Uotila P, Laato M: Differential effects of hexoses and sucrose, and platelet-derived growth factor isoforms on cyclooxygenase-1 and -2 mRNA expression in keloid, hypertrophic scar and granulation tissue fibroblasts. Arch Dermatol Res. 2001 Mar;293(3):126-32. [PubMed:11357226 ]
Gross KC, Houghton MP, Senterfit LB: Presumptive speciation of Streptococcus bovis and other group D streptococci from human sources by using arginine and pyruvate tests. J Clin Microbiol. 1975 Jan;1(1):54-60. [PubMed:1176592 ]
Fukasawa M, Takayama E, Shinomiya N, Okumura A, Rokutanda M, Yamamoto N, Sakakibara R: Identification of the promoter region of human placental 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase gene. Biochem Biophys Res Commun. 2000 Jan 27;267(3):703-8. [PubMed:10673355 ]
Le KA, Tappy L: Metabolic effects of fructose. Curr Opin Clin Nutr Metab Care. 2006 Jul;9(4):469-75. [PubMed:16778579 ]
Fukasawa M, Tsuchiya T, Takayama E, Shinomiya N, Uyeda K, Sakakibara R, Seki S: Identification and characterization of the hypoxia-responsive element of the human placental 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase gene. J Biochem. 2004 Sep;136(3):273-7. [PubMed:15598882 ]
Yanez AJ, Bertinat R, Spichiger C, Carcamo JG, de Los Angeles Garcia M, Concha II, Nualart F, Slebe JC: Novel expression of liver FBPase in Langerhans islets of human and rat pancreas. J Cell Physiol. 2005 Oct;205(1):19-24. [PubMed:15965961 ]
Lee YH, Li Y, Uyeda K, Hasemann CA: Tissue-specific structure/function differentiation of the liver isoform of 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase. J Biol Chem. 2003 Jan 3;278(1):523-30. Epub 2002 Oct 11. [PubMed:12379646 ]
Minchenko O, Opentanova I, Minchenko D, Ogura T, Esumi H: Hypoxia induces transcription of 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase-4 gene via hypoxia-inducible factor-1alpha activation. FEBS Lett. 2004 Oct 8;576(1-2):14-20. [PubMed:15474002 ]
Andrade-Rocha FT: Physical analysis of ejaculate to evaluate the secretory activity of the seminal vesicles and prostate. Clin Chem Lab Med. 2005;43(11):1203-10. [PubMed:16232086 ]
Roy S, Banerjee A, Pandey HC, Singh G, Kumari GL: Application of seminal germ cell morphology and semen biochemistry in the diagnosis and management of azoospermic subjects. Asian J Androl. 2001 Mar;3(1):55-62. [PubMed:11250795 ]
Blakemore SJ, Aledo JC, James J, Campbell FC, Lucocq JM, Hundal HS: The GLUT5 hexose transporter is also localized to the basolateral membrane of the human jejunum. Biochem J. 1995 Jul 1;309 ( Pt 1):7-12. [PubMed:7619085 ]
Abou El Fadil-Nicol F, Berger F, Descroix-Vagne M, Pansu D: Presence of sorbin in human digestive tract and endocrine digestive tumours. Gut. 2000 Feb;46(2):182-90. [PubMed:10644311 ]
Faeh D, Minehira K, Schwarz JM, Periasamy R, Park S, Tappy L: Effect of fructose overfeeding and fish oil administration on hepatic de novo lipogenesis and insulin sensitivity in healthy men. Diabetes. 2005 Jul;54(7):1907-13. [PubMed:15983189 ]
Atsumi T, Chesney J, Metz C, Leng L, Donnelly S, Makita Z, Mitchell R, Bucala R: High expression of inducible 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase (iPFK-2; PFKFB3) in human cancers. Cancer Res. 2002 Oct 15;62(20):5881-7. [PubMed:12384552 ]
Wu LY, Juan CC, Hwang LS, Hsu YP, Ho PH, Ho LT: Green tea supplementation ameliorates insulin resistance and increases glucose transporter IV content in a fructose-fed rat model. Eur J Nutr. 2004 Apr;43(2):116-24. Epub 2004 Jan 6. [PubMed:15083319 ]
Ludwig M, Vidal A, Diemer T, Pabst W, Failing K, Weidner W: Seminal secretory capacity of the male accessory sex glands in chronic pelvic pain syndrome (CPPS)/chronic prostatitis with special focus on the new prostatitis classification. Eur Urol. 2002 Jul;42(1):24-8. [PubMed:12121725 ]
Massucco P, Mattiello L, Russo I, Traversa M, Doronzo G, Anfossi G, Trovati M: High glucose rapidly activates the nitric oxide/cyclic nucleotide pathway in human platelets via an osmotic mechanism. Thromb Haemost. 2005 Mar;93(3):517-26. [PubMed:15735804 ]
Sugisawa T, Miyazaki T, Hoshino T: Microbial production of L-ascorbic acid from D-sorbitol, L-sorbose, L-gulose, and L-sorbosone by Ketogulonicigenium vulgare DSM 4025. Biosci Biotechnol Biochem. 2005 Mar;69(3):659-62. doi: 10.1271/bbb.69.659. [PubMed:15785002 ]

Enzymes

Enzyme Details

1. Sorbitol dehydrogenase

General function:: Involved in zinc ion binding
Specific function:: Converts sorbitol to fructose. Part of the polyol pathway that plays an important role in sperm physiology. May play a role in the sperm motility by providing an energetic source for sperm (By similarity).
Gene Name:: SORD
Uniprot ID:: Q00796
Molecular weight:: 38324.25

Reactions

L-Iditol + NAD → L-Sorbose + NADH	details

Showing metabocard for L-Sorbose (HMDB0001266)

MOL for HMDB0001266 (L-Sorbose)

3D MOL for HMDB0001266 (L-Sorbose)

3D SDF for HMDB0001266 (L-Sorbose)

3D-SDF for HMDB0001266 (L-Sorbose)

PDB for HMDB0001266 (L-Sorbose)

3D PDB for HMDB0001266 (L-Sorbose)

SMILES for HMDB0001266 (L-Sorbose)

INCHI for HMDB0001266 (L-Sorbose)

Structure for HMDB0001266 (L-Sorbose)

3D Structure for HMDB0001266 (L-Sorbose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions