Identification

Name
Acetoacetic Acid
Accession Number
DB01762  (EXPT00381, DB04025)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
4ZI204Y1MC
CAS number
541-50-4
Weight
Average: 102.0886
Monoisotopic: 102.031694058
Chemical Formula
C4H6O3
InChI Key
WDJHALXBUFZDSR-UHFFFAOYSA-N
InChI
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
IUPAC Name
3-oxobutanoic acid
SMILES
CC(=O)CC(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFumarylacetoacetaseNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDisease
PhenylketonuriaDisease
3-hydroxyisobutyric acid dehydrogenase deficiencyDisease
3-hydroxyisobutyric aciduriaDisease
Tyrosine MetabolismMetabolic
Valine, Leucine and Isoleucine DegradationMetabolic
Beta-Ketothiolase DeficiencyDisease
Tyrosinemia, transient, of the newbornDisease
Ketone Body MetabolismMetabolic
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDisease
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)Disease
Tyrosinemia Type 3 (TYRO3)Disease
Succinyl CoA: 3-ketoacid CoA transferase deficiencyDisease
Butyrate MetabolismMetabolic
3-Methylglutaconic Aciduria Type IIIDisease
Methylmalonic AciduriaDisease
Tyrosinemia Type IDisease
Isovaleric AciduriaDisease
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDisease
Disulfiram Action PathwayDrug action
Fatty Acid BiosynthesisMetabolic
Isobutyryl-coa dehydrogenase deficiencyDisease
Isovaleric acidemiaDisease
Phenylalanine and Tyrosine MetabolismMetabolic
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDisease
3-Methylglutaconic Aciduria Type IDisease
3-Methylglutaconic Aciduria Type IVDisease
AlkaptonuriaDisease
HawkinsinuriaDisease
Maple Syrup Urine DiseaseDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Erik Herkenrath, "Process for the production of 1,2-dihydro-2-oxo-4-methyl-7-acetoacetic acid amido-quinoline." U.S. Patent US4064131, issued July, 1956.

US4064131
General References
  1. Martin PM, Gopal E, Ananth S, Zhuang L, Itagaki S, Prasad BM, Smith SB, Prasad PD, Ganapathy V: Identity of SMCT1 (SLC5A8) as a neuron-specific Na+-coupled transporter for active uptake of L-lactate and ketone bodies in the brain. J Neurochem. 2006 Jul;98(1):279-88. [PubMed:16805814]
External Links
Human Metabolome Database
HMDB00060
KEGG Compound
C00164
PubChem Compound
96
PubChem Substance
46505003
ChemSpider
94
ChEBI
15344
ChEMBL
CHEMBL1230762
HET
AAE
PDB Entries
1e3w / 1fcp / 1qco / 1ujw / 1ysl / 2fcp / 2y7g / 3i09 / 3vdr

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)36.5 °CPhysProp
water solubility1E+006 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
pKa3.59 (at 0 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility240.0 mg/mLALOGPS
logP-0.47ALOGPS
logP-0.0015ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.54 m3·mol-1ChemAxon
Polarizability9.18 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9817
Blood Brain Barrier+0.9678
Caco-2 permeable-0.5194
P-glycoprotein substrateNon-substrate0.7736
P-glycoprotein inhibitor INon-inhibitor0.9274
P-glycoprotein inhibitor IINon-inhibitor0.9567
Renal organic cation transporterNon-inhibitor0.9551
CYP450 2C9 substrateNon-substrate0.8049
CYP450 2D6 substrateNon-substrate0.9101
CYP450 3A4 substrateNon-substrate0.7798
CYP450 1A2 substrateNon-inhibitor0.9394
CYP450 2C9 inhibitorNon-inhibitor0.9777
CYP450 2D6 inhibitorNon-inhibitor0.9614
CYP450 2C19 inhibitorNon-inhibitor0.9582
CYP450 3A4 inhibitorNon-inhibitor0.9731
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9924
Ames testNon AMES toxic0.9424
CarcinogenicityCarcinogens 0.5436
BiodegradationReady biodegradable0.9425
Rat acute toxicity1.8971 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9632
hERG inhibition (predictor II)Non-inhibitor0.9825
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00kk-3940000000-008eb78d2ba3cfa053b4
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-000i-9500000000-c3940e591f8aef9d6aac
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-000i-9800000000-67a95675672c3f5447a7
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-001i-4950000000-1778836b3908a79b814f
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-001i-4950000000-4039bb48c98ec17b5c0c
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kk-3940000000-008eb78d2ba3cfa053b4
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-9500000000-c3940e591f8aef9d6aac
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-9800000000-67a95675672c3f5447a7
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-4950000000-1778836b3908a79b814f
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-4950000000-4039bb48c98ec17b5c0c
MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)LC-MS/MSsplash10-000i-9200000000-9b4ab7b6a41632cb125b
MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)LC-MS/MSsplash10-0udi-6900000000-cfab9d4cdb56acafe8cc
MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)LC-MS/MSsplash10-0pb9-9800000000-108aa5ef93455fb1ba28
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-9100000000-869e2338bbadb32272d4
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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
Beta-keto acids and derivatives / Beta-hydroxy ketones / 1,3-dicarbonyl compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
3-oxo monocarboxylic acid, ketone body (CHEBI:15344) / Oxo fatty acids (C00164) / Oxo fatty acids (LMFA01060003)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
FAH
Uniprot ID
P16930
Uniprot Name
Fumarylacetoacetase
Molecular Weight
46373.97 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name
SLC16A7
Uniprot ID
O60669
Uniprot Name
Monocarboxylate transporter 2
Molecular Weight
52199.745 Da
References
  1. Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [PubMed:10417314]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Symporter activity
Specific Function
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name
SLC16A1
Uniprot ID
P53985
Uniprot Name
Monocarboxylate transporter 1
Molecular Weight
53943.685 Da
References
  1. Broer S, Rahman B, Pellegri G, Pellerin L, Martin JL, Verleysdonk S, Hamprecht B, Magistretti PJ: Comparison of lactate transport in astroglial cells and monocarboxylate transporter 1 (MCT 1) expressing Xenopus laevis oocytes. Expression of two different monocarboxylate transporters in astroglial cells and neurons. J Biol Chem. 1997 Nov 28;272(48):30096-102. [PubMed:9374487]
  2. Broer S, Schneider HP, Broer A, Rahman B, Hamprecht B, Deitmer JW: Characterization of the monocarboxylate transporter 1 expressed in Xenopus laevis oocytes by changes in cytosolic pH. Biochem J. 1998 Jul 1;333 ( Pt 1):167-74. [PubMed:9639576]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine...
Gene Name
SLC16A3
Uniprot ID
O15427
Uniprot Name
Monocarboxylate transporter 4
Molecular Weight
49468.9 Da
References
  1. Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [PubMed:11101640]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Symporter activity
Specific Function
Acts as an electrogenic sodium (Na(+)) and chloride (Cl-)-dependent sodium-coupled solute transporter, including transport of monocarboxylates (short-chain fatty acids including L-lactate, D-lactat...
Gene Name
SLC5A8
Uniprot ID
Q8N695
Uniprot Name
Sodium-coupled monocarboxylate transporter 1
Molecular Weight
66577.005 Da
References
  1. Martin PM, Gopal E, Ananth S, Zhuang L, Itagaki S, Prasad BM, Smith SB, Prasad PD, Ganapathy V: Identity of SMCT1 (SLC5A8) as a neuron-specific Na+-coupled transporter for active uptake of L-lactate and ketone bodies in the brain. J Neurochem. 2006 Jul;98(1):279-88. [PubMed:16805814]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:04