Livestock Metabolome Database: Showing metabocard for Dihydroxyacetone (LMDB00361)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:07 UTC

Update Date

2016-07-20 20:39:34 UTC

Lmdb

LMDB00361

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydroxyacetone

Description

Dihydroxyacetone is a ketotriose compound. Its addition to blood preservation solutions results in better maintenance of 2,3-diphosphoglycerate levels during storage. It is readily phosphorylated to dihydroxyacetone phosphate by triokinase in erythrocytes. In combination with naphthoquinones it acts as a sunscreening agent. -- Pubchem; Dihydroxyacetone (also known as DHA) is a triose carbohydrate with chemical formula C3H6O3. It is the simplest of all ketoses and, having no chiral centre, is the only one that has no optical activity. -- Wikipedia; Dihydroxyacetone is a simple non-toxic sugar. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin; it is a white crystalline powder which is water soluble. -- Wikipedia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dihydroxy-2-propanone	ChEBI
1,3-Dihydroxyacetone	ChEBI
1,3-Dihydroxydimethyl ketone	ChEBI
1,3-Dihydroxypropan-2-one	ChEBI
1,3-Dihydroxypropanone	ChEBI
1,3-Propanediol-2-one	ChEBI
alpha,Alpha'-dihydroxyacetone	ChEBI
Bis(hydroxymethyl) ketone	ChEBI
DHA	ChEBI
Glycerone	ChEBI
Chromelin	Kegg
a,Alpha'-dihydroxyacetone	Generator
Α,alpha'-dihydroxyacetone	Generator
a,A'-dihydroxyacetone	HMDB
Aliphatic ketone	HMDB
Dihydroxy-acetone	HMDB
Dihyxal	HMDB
Ketochromin	HMDB
Otan	HMDB
Oxantin	HMDB
Oxatone	HMDB
Protosol	HMDB
Soleal	HMDB
Triulose	HMDB
Viticolor	HMDB
1,3 Dihydroxy 2 propanone	HMDB
Summers brand OF dihydroxyacetone	HMDB
ICN brand OF dihydroxyacetone	HMDB
Vitadye	HMDB

Chemical Formula

C₃H₆O₃

Average Molecular Weight

90.0779

Monoisotopic Molecular Weight

90.031694058

IUPAC Name

1,3-dihydroxypropan-2-one

Traditional Name

dihydroxyacetone

CAS Registry Number

96-26-4

SMILES

OCC(=O)CO

InChI Identifier

InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2

InChI Key

RXKJFZQQPQGTFL-UHFFFAOYSA-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

Glycerone or derivatives
Monosaccharide
Alpha-hydroxy ketone
Ketone
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketotriose (CHEBI:16016 )
Ketoses (C00184 )
a small molecule (DIHYDROXYACETONE )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.6	ALOGPS
logP	-1.5	ChemAxon
logS	0.97	ALOGPS
pKa (Strongest Acidic)	13.49	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	19.6 m³·mol⁻¹	ChemAxon
Polarizability	8.1 Å³	ChemAxon
Number of Rings	0	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	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0w2j-1900000000-b3783d91181e1657545d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-0wa0-5900000000-f95dddc55209203877e3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gvk-1900000000-bd875a5207eb70c5beb8	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0w2j-1900000000-b3783d91181e1657545d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0wa0-5900000000-f95dddc55209203877e3	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0w2j-2900000000-f84cc49dd11822409add	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9000000000-089abb74f439c9265bb6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9320000000-6bdc226e79d3bc473a66	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-0e836f7fe0512bb62662	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-059i-9000000000-d1a13699d0d0cbea36b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-57da9a85ff22593c3ab3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-55ab07d1079db56cca4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-9000000000-f9afe28f3ce4c2f913d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-8e71e2b93a16e2be3db1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-7bb646a5cb5ca825e7b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fu-9000000000-ab60a50ef2013d762751	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-ef7c943cff3a9adfd1ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-3deebe0c487d3443c844	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-73f63f3caf2a9bf8b899	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-195717f89ffa991dcb57	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Ruminal Fluid	Detected and Quantified	17 +/- 5 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	7 +/- 2 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	7 +/- 2 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	7 +/- 3 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	112 +/- 6 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	17 +/- 5 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Ruminal Fluid	Detected and Quantified	6.4 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	7.2 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	7.9 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	15.6 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	6.3 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	6.5 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	6.8 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	16.6 uM	Not Available	Bovine	22959937	details