DrugBank: Acetoacetic Acid (DB01762)

targets (1) transporters (4)

Identification

Name

Acetoacetic Acid

Accession Number

DB01762 (DB04025, EXPT00381)

Type

small molecule

Groups

experimental

Description

Not Available

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Not Available

CAS number

541-50-4

Weight

Average: 102.0886
Monoisotopic: 102.031694058

Chemical Formula

C₄H₆O₃

InChI Key

InChIKey=WDJHALXBUFZDSR-UHFFFAOYSA-N

InChI

InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)

Plain Text

IUPAC Name

3-oxobutanoic acid

SMILES

CC(=O)CC(O)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Not Available

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

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	36.5 °C	PhysProp
water solubility	1E+006 mg/L (at 20 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
pKa	3.59 (at 0 °C)	KORTUM,G ET AL (1961)

Predicted Properties

Property	Value	Source
water solubility	2.40e+02 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	ChemAxon
rotatable bond count	2	ChemAxon
refractivity	22.54	ChemAxon
polarizability	9.18	ChemAxon

References

Synthesis Reference

Not Available

General Reference

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

Resource	Link
KEGG Compound	C00164
PubChem Compound	96
PubChem Substance	46505003
ChemSpider	94
ChEBI	15344
ChEMBL	15344
HET	AAE

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1QCO
2FCP

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Fumarylacetoacetase Pharmacological action: unknown Organism class: human UniProt ID: P16930 Gene: FAH SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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

Targets

1. Fumarylacetoacetase

Pharmacological action: unknown
Organism class: human
UniProt ID: P16930 Link_out

Gene: FAH
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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 Actions: inhibitor 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. MCT2 is a high affinity pyruvate transporter UniProt ID: O60669 Gene: SLC16A7 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Actions: substrate, inhibitor 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 UniProt ID: P53985 Gene: SLC16A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 Actions: substrate 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 UniProt ID: O15427 Gene: SLC16A3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 UniProt ID: Q8N695 References: 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

Transporters

1. Monocarboxylate transporter 2

Actions: inhibitor

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. MCT2 is a high affinity pyruvate transporter

UniProt ID: O60669 Link_out

Gene: SLC16A7 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Actions: substrate, inhibitor

UniProt ID: P53985 Link_out

Gene: SLC16A1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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

Actions: substrate

UniProt ID: O15427 Link_out

Gene: SLC16A3 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

UniProt ID: Q8N695 Link_out

References:

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 February 17, 2013 16:20