ChemFOnt: Showing chemical card for Alitame (CFc000018252)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:08:37 UTC

Chemfont ID

CFc000018252

Molecule Identification

Common Name

Alitame

Definition

Alitame is a sweetening agent. It is intensely sweet, approximately 2000 times sweeter than sucrose. Its use is currently (1999) permitted in Australia, New Zealand, Indonesia and China. Alitame is an artificial sweetener developed by Pfizer in the early 1980s and currently marketed in some countries under the brand name Aclame. Like aspartame, alitame is an aspartic acid-containing dipeptide. Most dipeptides are not sweet, but the unexpected discovery of aspartame in 1965 led to a search for similar compounds that shared its sweetness. Alitame is one such second-generation dipeptide sweetener. Neotame, developed by the owners of the NutraSweet brand, is another.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Alitame anhydrous	HMDB
CP 54802	HMDB
L-a-Aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide, 9ci	HMDB
3-Amino-3-({1-[(2,2,4,4-tetramethylthietan-3-yl)-C-hydroxycarbonimidoyl]ethyl}-C-hydroxycarbonimidoyl)propanoate	Generator

Chemical Formula

C₁₄H₂₅N₃O₄S

Average Molecular Weight

331.431

Monoisotopic Molecular Weight

331.156576993

IUPAC Name

3-amino-3-({1-[(2,2,4,4-tetramethylthietan-3-yl)carbamoyl]ethyl}carbamoyl)propanoic acid

Traditional Name

alitame

CAS Registry Number

80863-62-3

SMILES

CC(NC(=O)C(N)CC(O)=O)C(=O)NC1C(C)(C)SC1(C)C

InChI Identifier

InChI=1S/C14H25N3O4S/c1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5/h7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19)

InChI Key

IVBOUFAWPCPFTQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Heterocyclic fatty acid
N-acyl-amine
Fatty amide
Fatty acid
Fatty acyl
Thietane
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Dialkylthioether
Thioether
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037324)
Cytoplasm (HMDB: HMDB0037324)

Source

Exogenous

Exogenous (HMDB: HMDB0037324)

Food

Food (HMDB: HMDB0037324)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037324)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	0.24	ALOGPS
logP	-2.9	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.58 m³·mol⁻¹	ChemAxon
Polarizability	34.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037324

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016344

KNApSAcK ID

Not Available

Chemspider ID

13996684

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alitame

METLIN ID

Not Available

PubChem Compound

13362146

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Alitame (CFc000018252)

MOL for CFc000018252 (Alitame)

3D MOL for CFc000018252 (Alitame)

3D SDF for CFc000018252 (Alitame)

3D-SDF for CFc000018252 (Alitame)

PDB for CFc000018252 (Alitame)

3D PDB for CFc000018252 (Alitame)

SMILES for CFc000018252 (Alitame)

INCHI for CFc000018252 (Alitame)

Structure for CFc000018252 (Alitame)

3D Structure for CFc000018252 (Alitame)