MiMeDB: Showing metabocard for keto-L-sorbose (MMDBc0054524)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:16:42 UTC

Update Date

2022-08-12 20:09:00 UTC

Metabolite ID

MMDBc0054524

Metabolite Identification

Common Name

keto-L-sorbose

Description

keto-L-sorbose, also known as L-sorbose, 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. keto-L-sorbose is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041411192D          

 15 14  0  0  1  0            999 V2000
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  3  9  1  6  0  0  0
 10  4  2  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  6  0  0  0
  3 13  1  6  0  0  0
  5 14  1  6  0  0  0
  6 15  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054524

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=O)CO

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

> <INCHI_KEY>
BJHIKXHVCXFQLS-OTWZMJIISA-N

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.1559

> <EXACT_MASS>
180.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
16.320169096540614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-one

> <ALOGPS_LOGP>
-2.23

> <JCHEM_LOGP>
-3.2670318919999994

> <ALOGPS_LOGS>
0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.602831772026633

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.481384767416438

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9745010563329766

> <JCHEM_POLAR_SURFACE_AREA>
118.22

> <JCHEM_REFRACTIVITY>
37.56179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-sorbose

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3    7                                                       
CONECT    2    4    8                                                       
CONECT    3    1    5    9   13                                             
CONECT    4    2    6   10                                                  
CONECT    5    3    6   11   14                                             
CONECT    6    4    5   12   15                                             
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    3                                                            
CONECT   14    5                                                            
CONECT   15    6                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

Synonyms

Value	Source
(3S,4R,5S)-1,3,4,5,6-Pentahydroxyhexan-2-one	ChEBI
L-Sorbose	ChEBI
D-Sorbose	MeSH
L Sorbose	MeSH
Sorbose	MeSH
D Sorbose	MeSH

Molecular Formula

C₆H₁₂O₆

Average Mass

180.1559

Monoisotopic Mass

180.063388116

IUPAC Name

(3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-one

Traditional Name

L-sorbose

CAS Registry Number

Not Available

SMILES

[H][C@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=O)CO

InChI Identifier

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

InChI Key

BJHIKXHVCXFQLS-OTWZMJIISA-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

Monosaccharide
Beta-hydroxy ketone
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Polyol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-sorbose (CHEBI:13172 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	399 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3.3	ChemAxon
logS	0.35	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.56 m³·mol⁻¹	ChemAxon
Polarizability	16.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_7) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-1900000000-87bee64df7fe316d7aff	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-eb4eeb92523e2e200555	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fu-9100000000-3f790be8b14df714880b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0170-7900000000-041fe274da364a106e71	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9300000000-6f545044f1769c501e2b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-b0a05227494224e23bd2	2016-08-03	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012858	L-Iditol	Hydrogen Ion	Sorbitol dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0012859	L-Iditol	Hydrogen Ion	Sorbitol dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0013329	Sorbitol	Hydrogen Ion	Sorbose reductase SOU1	Reduction	RHEA	34755880
MMDBr0017142	keto-L-tagatose	keto-L-sorbose	Ketose 3-epimerase	Epimerization	RHEA	34755880
MMDBr0025322	keto-L-sorbose	L-Histidine	PTS system sorbose-specific EIIB component		RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Firmicutes	2	Human feces
Bacteria	Proteobacteria	1
Eukaryota/Fungi	Ascomycota	2
Bacteria/NULL	Actinobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6904

PDB ID

Not Available

ChEBI ID

13172

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for keto-L-sorbose (MMDBc0054524)

MOL for #<Metabolite:0x000055c79c5b7750>

3D MOL for #<Metabolite:0x000055c79c5b7750>

3D SDF for #<Metabolite:0x000055c79c5b7750>

3D-SDF for #<Metabolite:0x000055c79c5b7750>

PDB for #<Metabolite:0x000055c79c5b7750>

3D PDB for #<Metabolite:0x000055c79c5b7750>

SMILES for #<Metabolite:0x000055c79c5b7750>

INCHI for #<Metabolite:0x000055c79c5b7750>

Structure for #<Metabolite:0x000055c79c5b7750>

3D Structure for #<Metabolite:0x000055c79c5b7750>