MiMeDB: Showing metabocard for Acetoacetic acid (MMDBc0029464)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:19:27 UTC

Update Date

2024-10-07 02:59:34 UTC

Metabolite ID

MMDBc0029464

Metabolite Identification

Common Name

Acetoacetic acid

Description

Acetoacetic acid is a member of the chemical class known as Beta Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Acetoacetic acid (also called diacetic acid) is the organic compound with the formula CH3C(O)CH2CO2H. It is the simplest beta-keto acid group and like other members of this class is unstable. (WikiPedia)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

Molecular Formula

C₄H₆O₃

Average Mass

102.0886

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	240 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9500000000-c3940e591f8aef9d6aac	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9800000000-67a95675672c3f5447a7	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-4950000000-1778836b3908a79b814f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-4950000000-4039bb48c98ec17b5c0c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kk-3940000000-008eb78d2ba3cfa053b4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9500000000-c3940e591f8aef9d6aac	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9800000000-67a95675672c3f5447a7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-4950000000-1778836b3908a79b814f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-4950000000-4039bb48c98ec17b5c0c	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-9f6c0d100736f4d183c9	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0100-9600000000-470bf0676151478bca3e	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-9200000000-9b4ab7b6a41632cb125b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0udi-6900000000-cfab9d4cdb56acafe8cc	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0pb9-9800000000-108aa5ef93455fb1ba28	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9100000000-869e2338bbadb32272d4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0a4i-9000000000-3f979a5a82ec557199d2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9000000000-2b35e5493fb76f714c22	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-9000000000-d2734268ae2c1230e50f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-0d73b25163774c0d1eb1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-9400000000-081c4a1a05f5581a5ffb	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9100000000-960a06fd90db43d3e0f6	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-bd091454ccc8f532b42e	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-9700000000-b01f47bb6cd4f1043983	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9100000000-d2649829e8a79045e73b	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-1486ce68d51ba83ed499	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-9400000000-2f187d15e3b22b7629d9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9100000000-1e5e193606848f9d64b4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-73a6b61cfeb4b8ae9612	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-de86214ccec455e1860b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-42af30a03d7e2d4c22fc	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-6aa1f4078505fa3b0971	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Peroxisome

Biospecimen Locations

Blood
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Feces
Fibroblasts
Leukocyte
Liver
Neuron
Saliva
Spleen
Urine

Tissue Locations

Fibroblasts
Leukocyte
Liver
Neuron
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191685	Hydroxymethylglutaryl-CoA lyase, mitochondrial	Enzyme	P35914	Homo sapiens
MMDBp0191965	Aldehyde dehydrogenase, mitochondrial	Unknown	P05091	Homo sapiens
MMDBp0192187	D-beta-hydroxybutyrate dehydrogenase, mitochondrial	Unknown	Q02338	Homo sapiens
MMDBp0192351	Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrial	Enzyme	P55809	Homo sapiens
MMDBp0192352	Fumarylacetoacetase	Unknown	P16930	Homo sapiens
MMDBp0192353	Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrial	Enzyme	Q9BYC2	Homo sapiens
MMDBp0193939	Hydroxyacid-oxoacid transhydrogenase, mitochondrial	Unknown	Q8IWW8	Homo sapiens
MMDBp0193959	Acetoacetyl-CoA synthetase	Enzyme	Q86V21	Homo sapiens
MMDBp0193988	3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic	Enzyme	Q8TB92	Homo sapiens
MMDBp0194059	3-hydroxybutyrate dehydrogenase type 2	Unknown	Q9BUT1	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000215	Acetoacetic acid	Acetone	Not Available	VMH; KEGG	30371894
MMDBr0000379	(R)-3-Hydroxybutyric acid	Acetoacetic acid	3-hydroxybutyrate dehydrogenase, type 1	VMH; KEGG	1639787 8679568
MMDBr0001247	4-Fumarylacetoacetic acid	Acetoacetic acid	Not Available	VMH; KEGG	30371894
MMDBr0001451	3-Hydroxy-3-methylglutaryl-CoA	Acetoacetic acid	3-hydroxymethyl-3-methylglutaryl-CoA lyase	VMH	11129331
MMDBr0001452	3-Hydroxy-3-methylglutaryl-CoA	Acetoacetic acid	3-hydroxymethyl-3-methylglutaryl-CoA lyase	VMH	11111079
MMDBr0001820	Acetoacetic acid	Acetoacetyl-CoA	3-oxoacid CoA transferase 1	VMH; KEGG	30371894
MMDBr0002511	Acetoacetic acid	Acetoacetyl-CoA	acetoacetyl-CoA synthetase	VMH; KEGG	30371894
MMDBr0006907	Acetoacetic acid	Acetoacetyl-CoA	Not Available	VMH	30371894
MMDBr0007003	(S)-5-Amino-3-oxohexanoate	L-3-Aminobutyryl-CoA	Not Available	VMH	30371894
MMDBr0007513	Acetoacetic acid	Acetoacetyl-CoA	Not Available	VMH	30371894
MMDBr0007691	Acetoacetyl-CoA	Acetoacetic acid	Not Available	VMH	30371894
MMDBr0007730	(R)-3-Hydroxybutyric acid	Acetoacetic acid	Not Available	VMH	30371894
MMDBr0007869	3-Hydroxy-3-methylglutaryl-CoA	Acetoacetic acid	Not Available	VMH	30371894
MMDBr0008117	Acetoacetic acid	Acetoacetyl-CoA	Not Available	VMH; KEGG	30371894
MMDBr0010887	Acetoacetic acid	Acetoacetyl-CoA	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
2-ketoglutarate dehydrogenase complex deficiency		Association	Human Blood	HMDB	8295396
Anoxia	Decreased	Association	Human Cellular Cytoplasm	HMDB	8579834
Diabetes mellitus type 2	Increased	Association	Human Urine	HMDB	6321058
Diabetes mellitus type 2	Increased	Association	Human Blood	HMDB	15982426
Glucose transporter type 1 deficiency syndrome		Association	Human Cerebrospinal Fluid (CSF)	HMDB	14769490
Meningitis	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	15627241
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Ketosis	Decreased	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Ketosis		Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Ketosis	Decreased	Association	Human Urine	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Ketosis		Association	Human Urine	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Ketosis		Association	Human Urine	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	249	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Turkey	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	263	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	110	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	87	Human feces; Human appendix biopsy; Human ; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque; Human stool	Metabolic reconstruction
Bacteria	Synergistetes	6	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	38	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown
Bacteria	Candidatus cloacimonetes	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
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	100				uM	Newborn (0-30 days old)	Male	2-Ketoglutarate dehydrogenase complex deficiency	HMDB	8295396
Human Blood	Detected and Quantified			50	1280	uM	Children (1-13 years old)	Male	2-Ketoglutarate dehydrogenase complex deficiency	HMDB	8295396
Human Blood	Detected and Quantified	<30				uM	Children (1-13 years old)	Male	3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency	HMDB	9727719
Human Cellular cytoplasm	Detected and Quantified	1000		800	1200	uM	Adult (>18 years old)	Both	Anoxia	HMDB	8579834
Human Urine	Detected and Quantified	237				umol/mmol creatinine	Adult (>18 years old)	Both	Diabetes	HMDB	6321058
Human Blood	Detected and Quantified	3030.0	20.0			uM	Adult (>18 years old)	Both	Diabetes	HMDB	15982426
Human Blood	Detected and Quantified	14.5	5.1			uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Cerebrospinal fluid (csf)	Detected and Quantified	248	179			uM	Children (1-13 years old)	Not Specified	Glucose transporter type 1 deficiency syndrome	HMDB	14769490
Human Blood	Detected and Quantified	910				uM	Children (1-13 years old)	Male	Succinyl CoA: 3-ketoacid CoA transferase deficiency	HMDB	9521962
Human Blood	Detected and Quantified	1540				uM	Children (1-13 years old)	Male	Succinyl CoA: 3-ketoacid CoA transferase deficiency	HMDB	9521962
Human Blood	Detected and Quantified	18.9	9.8			uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Cerebrospinal fluid (csf)	Detected and Quantified	322.0		240.0	404.0	uM	Adult (>18 years old)	Both	Meningitis	HMDB	15627241
Human Blood	Detected and Quantified	12.64	8.21			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Blood	Detected and Quantified	13.9	7.3			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	16.15	9.18			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23535240
Human Blood	Detected and Quantified	16.5	9.6			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Blood	Detected and Quantified	18.8	9.7			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Blood	Detected and Quantified	360				uM	Infant (0-1 year old)	Male	Pyruvate dehydrogenase phosphatase deficiency	HMDB	172850
Human Urine	Detected and Quantified			5	28	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Blood	Detected and Quantified	<150				uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	172850
Human Blood	Detected and Quantified			0.0	86.0	uM	Adult (>18 years old)	Both	Normal	HMDB	9732980
Human Urine	Detected and Quantified	0.15		0.01	0.58	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	9869358
Human Urine	Detected and Quantified	0.20		0.020	0.82	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9869358
Human Urine	Detected and Quantified	11.1		2.2	24.9	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Cerebrospinal fluid (csf)	Detected and Quantified	12.0	14.0			uM	Adult (>18 years old)	Both	Normal	HMDB	18502700
Human Cellular cytoplasm	Detected and Quantified	1700		1500	1900	uM	Adult (>18 years old)	Both	Normal	HMDB	8579834
Human Blood	Detected and Quantified			20	90	uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	9521962
Human Blood	Detected and Quantified	21.0		0.0	86.0	uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Blood	Detected and Quantified			30	1400	uM	Not Specified	Not Specified	Normal	HMDB	8295396
Human Urine	Detected and Quantified	33.0		0.00	67.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	6321058
Human Blood	Detected and Quantified	37.75	25.96			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	40.6	36.5			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Cerebrospinal fluid (csf)	Detected and Quantified	6.0	6.0			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	8412012
Human Urine	Detected and Quantified	22.37	14.614			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	1.00		0.00	2.00	umol/mmol creatinine	Adult (>18 years old)	Both	Ketosis	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	10025.00		50.00	20000.00	umol/mmol creatinine	Children (1-13 years old)	Both	Ketosis	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	0.08		0	1.5	umol/mmol creatinine	Newborn (0-30 days old)	Both	Ketosis	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Urine	Detected and Quantified	0.1		0	1.5	umol/mmol creatinine	Infant (0-1 year old)	Both	Ketosis	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Urine	Detected and Quantified	1.6		0.2	5.8	umol/mmol creatinine	Children (1-13 years old)	Both	Ketosis	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Urine	Detected and Quantified	18.64	20.321			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Cerebrospinal fluid (csf)	Detected and Quantified	26.2	12.3			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Cerebrospinal fluid (csf)	Detected and Quantified	26.2	12.3			uM	Not Specified	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	10.70	4.33			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22800120
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27065191
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000060

DrugBank ID

DB01762

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112157

KNApSAcK ID

C00007458

Chemspider ID

KEGG Compound ID

C00164

BioCyc ID

3-KETOBUTYRATE

BiGG ID

Not Available

Wikipedia Link

Acetoacetic_acid

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

15344

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. [PubMed:3884391 ]
Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. doi: 10.1042/bj2170365. [PubMed:6696735 ]
Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. doi: 10.1021/ac00101a004. [PubMed:7762816 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. doi: 10.1007/BF00711898. [PubMed:8412012 ]
Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. doi: 10.1007/BF00164476. [PubMed:8579834 ]
Sato T, Oouchi M, Nagakubo H, Chiba T, Ogawa S, Sato C, Sugimura K, Fukuda M: Effect of pravastatin on plasma ketone bodies in diabetics with hypercholesterolemia. Tohoku J Exp Med. 1998 May;185(1):25-9. doi: 10.1620/tjem.185.25. [PubMed:9710942 ]
Fulop M, Murthy V, Michilli A, Nalamati J, Qian Q, Saitowitz A: Serum beta-hydroxybutyrate measurement in patients with uncontrolled diabetes mellitus. Arch Intern Med. 1999 Feb 22;159(4):381-4. doi: 10.1001/archinte.159.4.381. [PubMed:10030312 ]
Galey JB, Destree O, Dumats J, Genard S, Tachon P: Protection against oxidative damage by iron chelators: effect of lipophilic analogues and prodrugs of N,N'-bis(3,4,5-trimethoxybenzyl)ethylenediamine- N,N'-diacetic acid (OR10141). J Med Chem. 2000 Apr 6;43(7):1418-21. doi: 10.1021/jm9911635. [PubMed:10753479 ]
Krejsa CM, Schieven GL: Detection of oxidative stress in lymphocytes using dichlorodihydrofluorescein diacetate. Methods Mol Biol. 2000;99:35-47. doi: 10.1385/1-59259-054-3:35. [PubMed:10909075 ]
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Walker V, Mills GA, Mellor JM, Langley GJ, Farrant RD: A novel pyrroline-5-carboxylic acid and acetoacetic acid adduct in hyperprolinaemia type II. Clin Chim Acta. 2003 May;331(1-2):7-17. doi: 10.1016/s0009-8981(03)00077-9. [PubMed:12691858 ]
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Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. doi: 10.1002/nbm.944. [PubMed:15627241 ]
Tanaka Y, Ohdan H, Onoe T, Mitsuta H, Tashiro H, Itamoto T, Asahara T: Low incidence of acute rejection after living-donor liver transplantation: immunologic analyses by mixed lymphocyte reaction using a carboxyfluorescein diacetate succinimidyl ester labeling technique. Transplantation. 2005 May 15;79(9):1262-7. doi: 10.1097/01.tp.0000161667.99145.20. [PubMed:15880082 ]
Tasker RC, Lutman D, Peters MJ: Hyperventilation in severe diabetic ketoacidosis. Pediatr Crit Care Med. 2005 Jul;6(4):405-11. doi: 10.1097/01.PCC.0000164343.20418.37. [PubMed:15982426 ]
Polsky-Fisher SL, Cao H, Lu P, Gibson CR: Effect of cytochromes P450 chemical inhibitors and monoclonal antibodies on human liver microsomal esterase activity. Drug Metab Dispos. 2006 Aug;34(8):1361-6. doi: 10.1124/dmd.106.009704. Epub 2006 May 23. [PubMed:16720683 ]

Showing metabocard for Acetoacetic acid (MMDBc0029464)

MOL for #<Metabolite:0x00007f46d0700260>

3D MOL for #<Metabolite:0x00007f46d0700260>

3D SDF for #<Metabolite:0x00007f46d0700260>

3D-SDF for #<Metabolite:0x00007f46d0700260>

PDB for #<Metabolite:0x00007f46d0700260>

3D PDB for #<Metabolite:0x00007f46d0700260>

SMILES for #<Metabolite:0x00007f46d0700260>

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Structure for #<Metabolite:0x00007f46d0700260>

3D Structure for #<Metabolite:0x00007f46d0700260>