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targets (2) transporters (3)
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Identification
Name Aspartame
Accession Number DB00168 (NUTR00046)
Type small molecule
Groups approved, nutraceutical
Description

Flavoring agent sweeter than sugar, metabolized as phenylalanine and aspartic acid. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
1-Methyl N-L-alpha-aspartyl-L-phenylalanate
1-Methyl N-L-alpha-aspartyl-L-phenylalanine
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl ester
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl ester, stereoisomer
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acid
Asp-phe-ome
Aspartam [INN-French]
Aspartame [USAN:BAN:INN]
Aspartamo [INN-Spanish]
Aspartamum [INN-Latin]
Aspartylphenylalanine methyl ester
L-Aspartyl-L-phenylalanine methyl ester
Methyl aspartylphenylalanate
Methyl L-alpha-aspartyl-L-phenylalanate
Methyl L-aspartyl-L-phenylalanine
Methyl N-L-alpha-aspartyl-L-phenylalaninate
N-L-alpha-Aspartyl-L-phenylalanine 1-methyl ester
First Prev Next Last
Salts Not Available
Brand names
Name Company
Aminosweet Ajinomoto
Canderel
Equal
Nutrasweet
Tri-sweet
Brand mixtures Not Available
Categories
  • Dietary supplement
  • Micronutrient
  • Sweetening Agents
CAS number 22839-47-0
Weight Average: 294.3031
Monoisotopic: 294.121571696
Chemical Formula C14H18N2O5
InChI Key InChIKey=IAOZJIPTCAWIRG-QWRGUYRKSA-N
InChI
InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1
Plain Text
IUPAC Name
(3S)-3-amino-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
SMILES
COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Used as a diet supplement and sugar substitute.
Pharmacodynamics Aspartame (L-alpha-aspartyl-L-phenylalanine methyl ester) is a low-calorie sweetener used to sweeten a wide variety of low- and reduced-calorie foods and beverages, including low-calorie tabletop sweeteners. Aspartame is composed of two amino acids, aspartic acid and phenylalanine, as the methyl ester. Aspartic acid and phenylalanine are also found naturally in protein containing foods, including meats, grains and dairy products. Methyl esters are also found naturally in many foods such as fruits and vegetable and their juices. Upon digestion, aspartame breaks down into three components (aspartic acid, phenylalanine and methanol), which are then absorbed into the blood and used in normal body processes. Neither aspartame nor its components accumulates in the body. These components are used in the body in the same ways as when they are derived from common foods.
Mechanism of action 180 to 200 times sweeter than sucrose, it is metabolized as a protein and its subsequent amino-acids used up in there respective mechanisms.
Absorption Absorbed in the small intestine, aspartame is metabolized and absorbed very quickly.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Approximately 10% of aspartame (by weight) is broken down into methanol in the small intestine. Most of the methanol is absorbed and quickly converted into formaldehyde. Approximately 50% of aspartame (by weight) is broken down into phenylalanine. Approximately 40% of aspartame (by mass) is broken down into aspartic acid.
Route of elimination Not Available
Half life At room temperature, aspartame is most stable at pH 4.3, where its half-life is nearly 300 days. At pH 7 however, its half-life is only a few days.
Clearance Not Available
Toxicity Mild gastrointestinal side effects including diarrhea have been reported.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Aspartame powder 1.68 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 246.5 °C PhysProp
water solubility The solubility of aspartame in water is dependent on pH and temperature, the maximum solubility is reached at pH 2.2 (20 mg/mL at 25 °C) and the minimum solubility at pH 5.2 (pHi) is 13.5 mg/mL at 25 °C. Not Available
logP -0.1 Not Available
Predicted Properties
Property Value Source
water solubility 6.52e-01 g/l ALOGPS
logP -1.2 ALOGPS
logP -2.2 ChemAxon
logS -2.6 ALOGPS
pKa (strongest acidic) 3.53 ChemAxon
pKa (strongest basic) 8.53 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 118.72 ChemAxon
rotatable bond count 8 ChemAxon
refractivity 73.22 ChemAxon
polarizability 29.58 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D02381 Link_out
KEGG Compound C11045 Link_out
ChEBI 2877 Link_out
ChEMBL 2877 Link_out
PharmGKB PA448493 Link_out
HET PME Link_out
Wikipedia http://en.wikipedia.org/wiki/Aspartame Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (71.9 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Transient receptor potential cation channel subfamily V member 1

Pharmacological action: unknown
Actions: inducer

Receptor-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. May be involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL

Organism class: human
UniProt ID: Q8NER1 Link_out
Gene: TRPV1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Riera CE, Vogel H, Simon SA, le Coutre J: Artificial sweeteners and salts producing a metallic taste sensation activate TRPV1 receptors. Am J Physiol Regul Integr Comp Physiol. 2007 Aug;293(2):R626-34. Epub 2007 Jun 13. Pubmed

2. Taste receptor type 1 member 2

Pharmacological action: unknown
Actions: agonist

Putative taste receptor. TAS1R2/TAS1R3 recognizes diverse natural and synthetic sweeteners

Organism class: human
UniProt ID: Q8TE23 Link_out
Gene: TAS1R2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Xu H, Staszewski L, Tang H, Adler E, Zoller M, Li X: Different functional roles of T1R subunits in the heteromeric taste receptors. Proc Natl Acad Sci U S A. 2004 Sep 28;101(39):14258-63. Epub 2004 Sep 7. Pubmed
  4. Cui M, Jiang P, Maillet E, Max M, Margolskee RF, Osman R: The heterodimeric sweet taste receptor has multiple potential ligand binding sites. Curr Pharm Des. 2006;12(35):4591-600. Pubmed
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. Pubmed
  2. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. Pubmed

2. Solute carrier family 22 member 8

Actions: inhibitor

Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)

UniProt ID: Q8TCC7 Link_out
Gene: SLC22A8 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. Pubmed

3. Solute carrier family 22 member 11

Actions: inhibitor

Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds

UniProt ID: Q9NSA0 Link_out
Gene: SLC22A11 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19