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Identification
NameAcetoacetic Acid
Accession NumberDB01762  (DB04025, EXPT00381)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number541-50-4
WeightAverage: 102.0886
Monoisotopic: 102.031694058
Chemical FormulaC4H6O3
InChI KeyWDJHALXBUFZDSR-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Succinyl CoA: 3-ketoacid CoA transferase deficiencyDiseaseSMP00569
Ketone Body MetabolismMetabolicSMP00071
Butyrate MetabolismMetabolicSMP00073
Beta-Ketothiolase DeficiencyDiseaseSMP00173
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDiseaseSMP00237
Isovaleric AciduriaDiseaseSMP00238
Propionic AcidemiaDiseaseSMP00236
3-Methylglutaconic Aciduria Type IIIDiseaseSMP00140
3-Methylglutaconic Aciduria Type IVDiseaseSMP00141
3-hydroxyisobutyric acid dehydrogenase deficiencyDiseaseSMP00521
Isovaleric acidemiaDiseaseSMP00524
Valine, Leucine and Isoleucine DegradationMetabolicSMP00032
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDiseaseSMP00138
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00384
3-hydroxyisobutyric aciduriaDiseaseSMP00522
Maple Syrup Urine DiseaseDiseaseSMP00199
Methylmalonic AciduriaDiseaseSMP00200
Isobutyryl-coa dehydrogenase deficiencyDiseaseSMP00523
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDiseaseSMP00137
3-Methylglutaconic Aciduria Type IDiseaseSMP00139
Fatty Acid BiosynthesisMetabolicSMP00456
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)DiseaseSMP00369
PhenylketonuriaDiseaseSMP00206
Tyrosinemia Type 3 (TYRO3)DiseaseSMP00370
Phenylalanine and Tyrosine MetabolismMetabolicSMP00008
AlkaptonuriaDiseaseSMP00169
Tyrosine MetabolismMetabolicSMP00006
Tyrosinemia Type IDiseaseSMP00218
Dopamine beta-hydroxylase deficiencyDiseaseSMP00498
Tyrosinemia, transient, of the newbornDiseaseSMP00494
Monoamine oxidase-a deficiency (MAO-A)DiseaseSMP00533
HawkinsinuriaDiseaseSMP00190
Disulfiram Action PathwayDrug actionSMP00429
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9777
CYP450 2D6 substrateNon-inhibitor0.9614
CYP450 2C19 substrateNon-inhibitor0.9582
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point36.5 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MS1D NMR2D NMR
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 Reference
  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
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Fumarylacetoacetase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Fumarylacetoacetase P16930 Details

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
  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
  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

Transporters

1. Monocarboxylate transporter 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 2 O60669 Details

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

2. Monocarboxylate transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 1 P53985 Details

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
  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

3. Monocarboxylate transporter 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Monocarboxylate transporter 4 O15427 Details

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

4. Sodium-coupled monocarboxylate transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sodium-coupled monocarboxylate transporter 1 Q8N695 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15