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Identification
NameAspartame
Accession NumberDB00168  (NUTR00046)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

Flavoring agent sweeter than sugar, metabolized as phenylalanine and aspartic acid. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-Methyl N-L-alpha-aspartyl-L-phenylalanateNot AvailableNot Available
1-Methyl N-L-alpha-aspartyl-L-phenylalanineNot AvailableNot Available
1-methyl N-L-α-aspartyl-L-phenylalanateNot AvailableNot Available
3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl esterNot AvailableNot Available
3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acidNot AvailableNot Available
3-Amino-N-(α-carboxyphenethyl)succinamic acid N-methyl esterNot AvailableNot Available
3-Amino-N-(α-methoxycarbonylphenethyl) succinamic acidNot AvailableNot Available
Asp-phe-omeNot AvailableNot Available
AspartamFrenchINN
AspartameNot AvailableINN, BAN, USAN
AspartamoSpanishINN
AspartamumLatinINN
Aspartylphenylalanine methyl esterNot AvailableNot Available
L-Aspartyl-L-phenylalanine methyl esterNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AminosweetAjinomoto
CanderelMerisant
EqualMerisant
NutrasweetNutraSweet
Brand mixturesNot Available
Categories
CAS number22839-47-0
WeightAverage: 294.3031
Monoisotopic: 294.121571696
Chemical FormulaC14H18N2O5
InChI KeyIAOZJIPTCAWIRG-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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentPeptides
Alternative parentsAlpha Amino Acid Esters; N-acyl-alpha Amino Acids and Derivatives; Alpha Amino Acid Amides; Amphetamines and Derivatives; Fatty Acid Esters; Amino Fatty Acids; Dicarboxylic Acids and Derivatives; Secondary Carboxylic Acid Amides; Carboxylic Acid Esters; Carboxylic Acids; Enolates; Polyamines; Ethers; Monoalkylamines; Alcohols and Polyols
Substituentsalpha-amino acid ester; n-acyl-alpha amino acid or derivative; alpha-amino acid amide; alpha-amino acid or derivative; amphetamine or derivative; fatty acid ester; benzene; dicarboxylic acid derivative; carboxamide group; carboxylic acid ester; secondary carboxylic acid amide; polyamine; ether; carboxylic acid; enolate; amine; primary aliphatic amine; primary amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Pharmacology
IndicationUsed as a diet supplement and sugar substitute.
PharmacodynamicsAspartame (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 action180 to 200 times sweeter than sucrose, it is metabolized as a protein and its subsequent amino-acids used up in there respective mechanisms.
AbsorptionAbsorbed in the small intestine, aspartame is metabolized and absorbed very quickly.
Volume of distributionNot Available
Protein bindingNot 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 eliminationNot Available
Half lifeAt 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.
ClearanceNot Available
ToxicityMild gastrointestinal side effects including diarrhea have been reported.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.8218
Blood Brain Barrier - 0.5562
Caco-2 permeable - 0.8956
P-glycoprotein substrate Substrate 0.5137
P-glycoprotein inhibitor I Non-inhibitor 0.9286
P-glycoprotein inhibitor II Non-inhibitor 0.9772
Renal organic cation transporter Non-inhibitor 0.9573
CYP450 2C9 substrate Non-substrate 0.833
CYP450 2D6 substrate Non-substrate 0.8474
CYP450 3A4 substrate Non-substrate 0.6928
CYP450 1A2 substrate Non-inhibitor 0.8972
CYP450 2C9 substrate Non-inhibitor 0.894
CYP450 2D6 substrate Non-inhibitor 0.9549
CYP450 2C19 substrate Non-inhibitor 0.9484
CYP450 3A4 substrate Non-inhibitor 0.9437
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9792
Ames test Non AMES toxic 0.7963
Carcinogenicity Non-carcinogens 0.9284
Biodegradation Not ready biodegradable 0.7073
Rat acute toxicity 1.6896 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9948
hERG inhibition (predictor II) Non-inhibitor 0.9467
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Aspartame powder1.68USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting pointabout 190 and 245-247Schlatter, J.M.; US.Patent 3,492,131; January 27, 1970; assigned to G.D. Searle & Co.
water solubilityThe 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-0.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.652ALOGPS
logP-1.2ALOGPS
logP-2.2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)8.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.72 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.22 m3·mol-1ChemAxon
Polarizability29.58 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
References
Synthesis Reference

Josef Tsau, “Convenient to use aspartame and method of making.” U.S. Patent US5582351, issued August, 1972.

US5582351
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD02381
KEGG CompoundC11045
ChEBI2877
ChEMBLCHEMBL171679
PharmGKBPA448493
HETPME
WikipediaAspartame
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(71.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Transient receptor potential cation channel subfamily V member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Transient receptor potential cation channel subfamily V member 1 Q8NER1 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Taste receptor type 1 member 2 Q8TE23 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. 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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 11 Q9NSA0 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08