Bovine Metabolome Database: Showing metabocard for L-Sorbose (BMDB0001266)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:43:19 UTC

Update Date

2020-06-04 20:32:37 UTC

BMDB ID

BMDB0001266

Secondary Accession Numbers

BMDB01266

Metabolite Identification

Common Name

L-Sorbose

Description

D-Fructose, also known as D-tagatose or D-lyxo-2-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. D-Fructose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Fructose exists in all living species, ranging from bacteria to humans. D-Fructose participates in a number of enzymatic reactions, within cattle. In particular, D-Fructose can be biosynthesized from sorbitol through its interaction with the enzyme sorbitol dehydrogenase. In addition, D-Fructose can be biosynthesized from Beta-D-fructose 2-phosphate through the action of the enzyme 14 kda phosphohistidine phosphatase. In cattle, D-fructose is involved in the metabolic pathway called the fructose and mannose degradation pathway. D-Fructose is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

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

87-79-6

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

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	165 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	360.0 mg/mL at 17 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-9700000000-3e5e0a3aa6c676c97701	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-004i-8422790000-fda815da7846441c6ea7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0900000000-ad56c2283c4948268668	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ri-9600000000-f53f9ae5db12b8c07611	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0079-9200000000-c3dabd4edd0fd062cfd4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-014681a0ceccca243630	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-2900000000-fdd4f1c2b01b7cd4a621	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c30-9200000000-a3afc1e71049f23145b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fu-9700000000-86b1b9f75df959e2158f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-024i-9800000000-1acd95dd1e6f8744308f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-545f59c3707e4298b57c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01pk-0900000000-d9de28ed437f1079125e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-9700000000-21b6c695fb9bdd5ae08d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-7c49e3a2d60cfed68a76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-6900000000-def874fe6470032fdd27	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9100000000-b495c0f16251b5ee98e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-d526231c78d5ea2b9be5	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adipose Tissue
Fibroblasts
Intestine
Kidney
Liver
Mammary Gland
Neuron
Pancreas
Placenta
Platelet
Prostate Tissue
Ruminal Fluid
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	763.813 +/- 751.731 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	763.813 +/- 751.731 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Ruminal Fluid	Detected and Quantified	2415.813 +/- 1248.434 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	2415.813 +/- 1248.434 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details

External Links

HMDB ID

HMDB0001266

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

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

Not Available

Enzymes

Enzyme Details

1. Sorbitol dehydrogenase

General function:: Amino acid transport and metabolism
Specific function:: Polyol dehydrogenase that catalyzes the reversible NAD(+)-dependent oxidation of various sugar alcohols. Is mostly active with xylitol, D-sorbitol (D-glucitol) and L-iditol as substrates, leading to the C2-oxidized products D-xylulose, D-fructose and L-sorbose, respectively (PubMed:9143345). Is a key enzyme in the polyol pathway that interconverts glucose and fructose via sorbitol, which constitutes an important alternate route for glucose metabolism. May play a role in sperm motility by using sorbitol as an alternative energy source for sperm motility (By similarity). Cannot use NADP(+) as the electron acceptor. Has no activity on ethanol, methanol, glycerol, galactitol and fructose 6-phosphate (PubMed:9143345).
Gene Name:: SORD
Uniprot ID:: Q58D31
Molecular weight:: 38099.0

Showing metabocard for L-Sorbose (BMDB0001266)

Structure for BMDB0001266 (L-Sorbose)

Enzymes