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Identification
NameAcetoacetic Acid
Accession NumberDB01762  (EXPT00381, DB04025)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII4ZI204Y1MC
CAS number541-50-4
WeightAverage: 102.0886
Monoisotopic: 102.031694058
Chemical FormulaC4H6O3
InChI KeyInChIKey=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
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
Related Articles
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
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDiseaseSMP00138
PhenylketonuriaDiseaseSMP00206
3-hydroxyisobutyric acid dehydrogenase deficiencyDiseaseSMP00521
3-hydroxyisobutyric aciduriaDiseaseSMP00522
Ketone Body MetabolismMetabolicSMP00071
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDiseaseSMP00237
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)DiseaseSMP00369
Tyrosinemia Type 3 (TYRO3)DiseaseSMP00370
Succinyl CoA: 3-ketoacid CoA transferase deficiencyDiseaseSMP00569
Tyrosine MetabolismMetabolicSMP00006
Valine, Leucine and Isoleucine DegradationMetabolicSMP00032
Beta-Ketothiolase DeficiencyDiseaseSMP00173
Tyrosinemia, transient, of the newbornDiseaseSMP00494
Butyrate MetabolismMetabolicSMP00073
3-Methylglutaconic Aciduria Type IIIDiseaseSMP00140
Methylmalonic AciduriaDiseaseSMP00200
Tyrosinemia Type IDiseaseSMP00218
Isovaleric AciduriaDiseaseSMP00238
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00384
Disulfiram Action PathwayDrug actionSMP00429
Fatty Acid BiosynthesisMetabolicSMP00456
Isobutyryl-coa dehydrogenase deficiencyDiseaseSMP00523
Isovaleric acidemiaDiseaseSMP00524
Phenylalanine and Tyrosine MetabolismMetabolicSMP00008
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDiseaseSMP00137
3-Methylglutaconic Aciduria Type IDiseaseSMP00139
3-Methylglutaconic Aciduria Type IVDiseaseSMP00141
AlkaptonuriaDiseaseSMP00169
HawkinsinuriaDiseaseSMP00190
Maple Syrup Urine DiseaseDiseaseSMP00199
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 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 )
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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00kk-3940000000-008eb78d2ba3cfa053b4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9500000000-c3940e591f8aef9d6aacView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9800000000-67a95675672c3f5447a7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-1778836b3908a79b814fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-4039bb48c98ec17b5c0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-9b4ab7b6a41632cb125bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-6900000000-cfab9d4cdb56acafe8ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pb9-9800000000-108aa5ef93455fb1ba28View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Not Available
Gene Name:
FAH
Uniprot ID:
P16930
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 leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Functions as high-affinity pyruvate transporter.
Gene Name:
SLC16A7
Uniprot ID:
O60669
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
substrateinhibitor
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 leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Depending on the tissue and on cicumstances, mediates the import or export of lactic acid and ketone bod...
Gene Name:
SLC16A1
Uniprot ID:
P53985
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, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate (By similarity).
Gene Name:
SLC16A3
Uniprot ID:
O15427
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-lactate, pyruvate, acetate, propionate, valerate and butyrate), lactate, mocarboxylate drugs (nicotinate, benzoate, salicylate and 5-aminosalicylate) and ketone bodies (beta-D-hydroxybutyrate, acetoacetate ...
Gene Name:
SLC5A8
Uniprot ID:
Q8N695
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 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15