Livestock Metabolome Database: Showing metabocard for Acetone (LMDB00352)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:56 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00352

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acetone

Description

Acetone is one of the ketone bodies produced during ketoacidosis. Acetone is not regarded as a waste product of metabolism. However, its physiological role in biochemical machinery is not clear. A model for the role of acetone metabolism is presented that orders the events occurring in acetonemia in sequence: in diabetic ketosis or starvation, ketone body production (b-hydroxy-butyrate, acetoacetate) provides fuel for vital organs (heart, brain .) raising the chance of survival of the metabolic catastrophe. However, when ketone body production exceeds the degrading capacity, the accumulating acetoacetic acid presents a new challenge to the pH regulatory system. Acetone production and its further degradation to C3 fragments fulfill two purposes: the maintenance of pH buffering capacity and provision of fuel for peripheral tissues. Since ketosis develops under serious metabolic circumstances, all the mechanisms that balance or moderate the effects of ketosis enhance the chance for survival. From this point of view, the theory that transportable C3 fragments can serve as additional nutrients is a novel view of acetone metabolism which introduces a new approach to the study of acetone degradation, especially in understanding its physiological function and the interrelationship between liver and peripheral tissues. (PMID 10580530 ). Acetone is typically derived from acetoacetate through the action of microbial acetoacetate decarboxylases found in gut microflora. In chemistry, acetone is the simplest representative of the ketones. Acetone is a colorless, mobile, flammable liquid readily soluble in water, ethanol, ether, etc., and itself serves as an important solvent. Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Propanone	ChEBI
Aceton	ChEBI
Azeton	ChEBI
beta-Ketopropane	ChEBI
Dimethyl ketone	ChEBI
Dimethylcetone	ChEBI
Dimethylketon	ChEBI
Dimethylketone	ChEBI
Methyl ketone	ChEBI
Propanon	ChEBI
Propanone	ChEBI
Pyroacetic ether	ChEBI
b-Ketopropane	Generator
Β-ketopropane	Generator
Dimethylformaldehyde	HMDB

Chemical Formula

C₃H₆O

Average Molecular Weight

58.0791

Monoisotopic Molecular Weight

58.041864814

IUPAC Name

propan-2-one

Traditional Name

acetone

CAS Registry Number

67-64-1

SMILES

CC(C)=O

InChI Identifier

InChI=1S/C3H6O/c1-3(2)4/h1-2H3

InChI Key

CSCPPACGZOOCGX-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methyl ketone (CHEBI:15347 )
propanone (CHEBI:15347 )
ketone body (CHEBI:15347 )
Oxygenated hydrocarbons (LMFA12000057 )
a methyl-ethyl-ketone (ACETONE )

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	-0.29	ALOGPS
logP	0.11	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	19.51	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	16.19 m³·mol⁻¹	ChemAxon
Polarizability	6.41 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 - EI-B (Non-derivatized)	splash10-052f-9000000000-14f33068e4ba092deb77	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-23fa1a3953b34b4d17db	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5de48058c986d7c07ac3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-ac4e03d64a5d08cb0e2d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-14f33068e4ba092deb77	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-23fa1a3953b34b4d17db	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5de48058c986d7c07ac3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-ac4e03d64a5d08cb0e2d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-bc353e3a40f83275872b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-9000000000-cbc26702df42f89389a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052f-9000000000-76023af14a12c4b19cf9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-9000000000-4a0900faf782fa344db9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-052f-9000000000-cd6003561b339cd9243f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-23fa1a3953b34b4d17db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-5de48058c986d7c07ac3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-31f47c962fee2ab51810	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-29f0bd4f29c752b098b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-44feb4a0693788e21f10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-e3c53a345dc69a6403f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-786aa0674415a8c32182	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-3bc848ca563aa39df37e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-6e3379842f4da69e8e2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-6e3379842f4da69e8e2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9251850c7854d63a048f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-7d56b578e5d5ea65f901	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-f1d310daeae27abc7672	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3f1c663ba1bd7d012172	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-e24ae6a1f2f0e7aac3e7	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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	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
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Plasma
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected and Quantified	17-497 uM	Not Available	Bovine	22098372	details
Milk	Detected and Quantified	12-661 uM	Not Available	Bovine	20338431	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	24937646	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	24937646	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24440255	details
Serum	Detected and Quantified	11.0332 +/- 8.3043 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.0481 +/- 9.4519 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	22.3864 +/- 12.315 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.2747 +/- 9.0334 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.8153 +/- 7.0316 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	12.6912 +/- 7.5905 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.7785 +/- 14.2937 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	13.4511 +/- 11.2184 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.04 +/- 6.18 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	16.1216 +/- 10.9127 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	22.1498 +/- 9.5335 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.0721 +/- 4.1882 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected and Quantified	16.2335 +/- 10.0108 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.1382 +/- 6.549 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	20.8523 +/- 14.4695 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	10.0347 +/- 5.4196 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	11.8798 +/- 8.1698 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	11.0674 +/- 10.0906 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	14.559 +/- 8.4856 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	24.9262 +/- 15.6283 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	9.9003 +/- 5.2601 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details