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Identification
NameAcetoacetic Acid
Accession NumberDB01762  (DB04025, EXPT00381)
Typesmall molecule
Groupsexperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassKeto-Acids and Derivatives
SubclassBeta Keto-Acids and Derivatives
Direct parentBeta Keto-Acids and Derivatives
Alternative parentsKetones; Polyamines; Enolates; Carboxylic Acids; Keto Acids and Derivatives
Substituentsketo acid; ketone; polyamine; enolate; carboxylic acid derivative; carboxylic acid; carbonyl group
Classification descriptionThis compound belongs to the beta keto-acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9817
Blood Brain Barrier + 0.9678
Caco-2 permeable - 0.5194
P-glycoprotein substrate Non-substrate 0.7736
P-glycoprotein inhibitor I Non-inhibitor 0.9274
P-glycoprotein inhibitor II Non-inhibitor 0.9567
Renal organic cation transporter Non-inhibitor 0.9551
CYP450 2C9 substrate Non-substrate 0.8049
CYP450 2D6 substrate Non-substrate 0.9101
CYP450 3A4 substrate Non-substrate 0.7798
CYP450 1A2 substrate Non-inhibitor 0.9394
CYP450 2C9 substrate Non-inhibitor 0.9777
CYP450 2D6 substrate Non-inhibitor 0.9614
CYP450 2C19 substrate Non-inhibitor 0.9582
CYP450 3A4 substrate Non-inhibitor 0.9731
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9924
Ames test Non AMES toxic 0.9424
Carcinogenicity Carcinogens 0.5436
Biodegradation Ready biodegradable 0.9425
Rat acute toxicity 1.8971 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9632
hERG inhibition (predictor II) Non-inhibitor 0.9825
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 solubility2.40e+02 g/lALOGPS
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 area54.37ChemAxon
rotatable bond count2ChemAxon
refractivity22.54ChemAxon
polarizability9.18ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
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
ResourceLink
KEGG CompoundC00164
PubChem Compound96
PubChem Substance46505003
ChemSpider94
ChEBI15344
ChEMBL
HETAAE
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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

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

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