Livestock Metabolome Database: Showing metabocard for Acetoacetic acid (LMDB00026)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:45 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00026

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acetoacetic acid

Description

It is a weak organic acid and can be produced in the animal liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis), it is then partially converted to acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. These compounds serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 wk of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life. (PMID 3884391 ) The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
3-Ketobutanoic acid	ChEBI
3-Ketobutyric acid	ChEBI
3-Oxobutanoic acid	ChEBI
3-Oxobutyric acid	ChEBI
beta-Ketobutyric acid	ChEBI
3-Ketobutanoate	Generator
3-Ketobutyrate	Generator
3-Oxobutanoate	Generator
3-Oxobutyrate	Generator
b-Ketobutyrate	Generator
b-Ketobutyric acid	Generator
beta-Ketobutyrate	Generator
Β-ketobutyrate	Generator
Β-ketobutyric acid	Generator
Acetoacetate	Generator
Acetoacetic acid, calcium salt	MeSH
Acetoacetic acid, lithium salt	MeSH
Acetoacetic acid, sodium salt	MeSH
Oxobutyrate	MeSH
Sodium acetoacetate	MeSH
3-oxo-Butanoate	HMDB
3-oxo-Butanoic acid	HMDB
Diacetate	HMDB
Diacetic acid	HMDB

Chemical Formula

C₄H₆O₃

Average Molecular Weight

102.0886

Monoisotopic Molecular Weight

102.031694058

IUPAC Name

3-oxobutanoic acid

Traditional Name

acetoacetic acid

CAS Registry Number

541-50-4

SMILES

CC(=O)CC(O)=O

InChI Identifier

InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)

InChI Key

WDJHALXBUFZDSR-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Beta-keto acid
1,3-dicarbonyl compound
Beta-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-oxo monocarboxylic acid (CHEBI:15344 )
ketone body (CHEBI:15344 )
Oxo fatty acids (C00164 )
Oxo fatty acids (LMFA01060003 )

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	-0.47	ALOGPS
logP	-0.0015	ChemAxon
logS	0.37	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.54 m³·mol⁻¹	ChemAxon
Polarizability	9.18 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)	splash10-00kk-3940000000-008eb78d2ba3cfa053b4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9500000000-c3940e591f8aef9d6aac	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9800000000-67a95675672c3f5447a7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-4950000000-1778836b3908a79b814f	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-4950000000-4039bb48c98ec17b5c0c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kk-3940000000-008eb78d2ba3cfa053b4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9500000000-c3940e591f8aef9d6aac	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9800000000-67a95675672c3f5447a7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-4950000000-1778836b3908a79b814f	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-4950000000-4039bb48c98ec17b5c0c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-9f6c0d100736f4d183c9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0100-9600000000-470bf0676151478bca3e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-9200000000-9b4ab7b6a41632cb125b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0udi-6900000000-cfab9d4cdb56acafe8cc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0pb9-9800000000-108aa5ef93455fb1ba28	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9100000000-869e2338bbadb32272d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0a4i-9000000000-3f979a5a82ec557199d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9000000000-2b35e5493fb76f714c22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-9000000000-d2734268ae2c1230e50f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-0d73b25163774c0d1eb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-9400000000-081c4a1a05f5581a5ffb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9100000000-960a06fd90db43d3e0f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-bd091454ccc8f532b42e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-9700000000-b01f47bb6cd4f1043983	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9100000000-d2649829e8a79045e73b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-1486ce68d51ba83ed499	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-9400000000-2f187d15e3b22b7629d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9100000000-1e5e193606848f9d64b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-73a6b61cfeb4b8ae9612	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-de86214ccec455e1860b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-42af30a03d7e2d4c22fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-6aa1f4078505fa3b0971	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
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
Plasma
Ruminal Fluid
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected and Quantified	4-14 uM	Not Available	Bovine	22098372	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23738862	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	Trabi M, Keller M...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	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
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	21496096	details
Ruminal Fluid	Detected and Quantified	141 +/- 16 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	70.8 +/- 6.9 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	84.7 +/- 17 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	564 +/- 56 uM	Not Available	Caprine	22706048	details
Ruminal Fluid	Detected and Quantified	48 +/- 17 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	64 +/- 9 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	68 +/- 9 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	68 +/- 9 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	78 +/- 15 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	80 +/- 27 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	64.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	67.7 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	77.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	80.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	47.1 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	49.5 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	54.1 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	58 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Serum	Detected and Quantified	8.2206 +/- 3.004 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	25.3298 +/- 15.9583 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	36.3285 +/- 24.6503 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	26.234 +/- 8.0583 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	9.7659 +/- 4.9385 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	7.67 +/- 3.09 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	25.0263 +/- 16.204 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	20.0924 +/- 10.9962 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.6432 +/- 2.9246 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.5897 +/- 7.8661 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	21.2791 +/- 13.185 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.4646 +/- 3.7582 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	23394630	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected and Quantified	20.118 +/- 12.8336 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.5074 +/- 10.0979 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	48.1205 +/- 35.1489 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.4463 +/- 4.8879 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	9.2041 +/- 3.6766 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	24.6698 +/- 18.0621 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.055 +/- 8.1151 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	47.4244 +/- 29.1011 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	15.5044 +/- 5.2136 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	Federica Murgia, ...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	24696864	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details