NP-MRD: Showing NP-Card for Neotame (NP0337847)

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Record Information

Version

2.0

Created at

2024-09-11 12:43:13 UTC

Updated at

2024-09-11 12:43:13 UTC

NP-MRD ID

NP0337847

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neotame

Description

Neotame was first documented in 2022 (PMID: 36461268). Based on a literature review a significant number of articles have been published on Neotame (PMID: 38340820) (PMID: 38041977) (PMID: 39234311) (PMID: 39079360) (PMID: 38766027) (PMID: 38721028).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262315152D          

 27 27  0  0  0  0            999 V2000
   -2.8493    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5933    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5933    1.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8493    1.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890    1.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406    0.1578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7845    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -0.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890    0.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933    0.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406    1.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    1.9741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317    1.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -0.8334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9379   -0.7509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0407    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858   -1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280   -0.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1876   -0.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1888   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  2  0  0  0  0
 11 12  1  0  0  0  0
 11 19  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END


  Mrv2104 05262315152D          

 27 27  0  0  0  0            999 V2000
   -2.8493    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5933    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5933    1.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8493    1.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890    1.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406    0.1578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7845    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -0.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890    0.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316    0.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933    0.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406    1.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    1.9741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317    1.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -0.8334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9379   -0.7509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0407    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858   -1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280   -0.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1876   -0.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1888   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  2  0  0  0  0
 11 12  1  0  0  0  0
 11 19  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337847

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(O)=O)NCCC(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1/C20H30N2O5/c1-20(2,3)10-11-21-15(13-17(23)24)18(25)22-16(19(26)27-4)12-14-8-6-5-7-9-14/h5-9,15-16,21H,10-13H2,1-4H3,(H,22,25)(H,23,24)

> <INCHI_KEY>
HLIAVLHNDJUHFG-UHFFFAOYNA-N

> <FORMULA>
C20H30N2O5

> <MOLECULAR_WEIGHT>
378.469

> <EXACT_MASS>
378.215472074

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.84676332055236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(3,3-dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid

> <JCHEM_LOGP>
-0.08332551252345978

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.450348417285255

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.601769523678115

> <JCHEM_PKA_STRONGEST_BASIC>
9.224138396974931

> <JCHEM_POLAR_SURFACE_AREA>
104.73

> <JCHEM_REFRACTIVITY>
100.8901

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3,3-dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -5.319   0.138   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.707   0.910   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.707   2.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.319   3.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.086   2.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.086   0.910   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.543   0.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.311   1.063   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.076   0.295   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.464   0.910   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.697  -0.015   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.086   0.756   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.472   0.138   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.707   0.910   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.076   3.375   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.311   2.604   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.390   3.685   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.926   2.296   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       2.697  -1.556   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       5.484  -1.402   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.809   3.685   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.467  -2.265   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.239  -1.558   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.989  -2.265   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.217  -1.558   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.989  -3.685   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.219  -2.975   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16    8   15   17                                                  
CONECT   17   16   21                                                       
CONECT   18   10                                                            
CONECT   19   11   22                                                       
CONECT   20   13                                                            
CONECT   21   17                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀N₂O₅

Average Mass

378.4690 Da

Monoisotopic Mass

378.21547 Da

IUPAC Name

3-[(3,3-dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid

Traditional Name

3-[(3,3-dimethylbutyl)amino]-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl]propanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(O)=O)NCCC(C)(C)C

InChI Identifier

InChI=1/C20H30N2O5/c1-20(2,3)10-11-21-15(13-17(23)24)18(25)22-16(19(26)27-4)12-14-8-6-5-7-9-14/h5-9,15-16,21H,10-13H2,1-4H3,(H,22,25)(H,23,24)

InChI Key

HLIAVLHNDJUHFG-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.083	ChemAxon
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.73 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	100.89 m³·mol⁻¹	ChemAxon
Polarizability	40.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Neotame

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang L, Yu Z, Zhao Y, Yin D: Obesogenic potentials of environmental artificial sweeteners with disturbances on both lipid metabolism and neural responses. Sci Total Environ. 2024 Apr 1;919:170755. doi: 10.1016/j.scitotenv.2024.170755. Epub 2024 Feb 9. [PubMed:38340820 ]
Cheng S, Wang S, Zheng M, Jin Y, Li J, Zhang M, Li XL, Min JZ: Simultaneous analysis of natural and artificial sweeteners in sugar-free drinks and urine samples by column-switching UHPLC-charged aerosol detection method. J Chromatogr A. 2024 Jan 4;1713:464533. doi: 10.1016/j.chroma.2023.464533. Epub 2023 Nov 28. [PubMed:38041977 ]
Farag MA, Rezk MM, Hamdi Elashal M, El-Araby M, Khalifa SAM, El-Seedi HR: An updated multifaceted overview of sweet proteins and dipeptides as sugar substitutes; the chemistry, health benefits, gut interactions, and safety. Food Res Int. 2022 Dec;162(Pt A):111853. doi: 10.1016/j.foodres.2022.111853. Epub 2022 Aug 24. [PubMed:36461268 ]
Yan X, Chen Z, Rong X, Chen Z, Wu G, Dong Z, Fu Y, Hai T: The impact of sucralose and neotame on the safety of metal precipitation in electronic cigarettes. Front Physiol. 2024 Aug 21;15:1437042. doi: 10.3389/fphys.2024.1437042. eCollection 2024. [PubMed:39234311 ]
Wang M, Ling L, Wang S, Ding CF: A homogeneous binary matrix assisted laser desorption/ionization time-of-flight mass spectrometry assay for determination of artificial sweeteners in beverages. Food Chem. 2024 Dec 1;460(Pt 2):140597. doi: 10.1016/j.foodchem.2024.140597. Epub 2024 Jul 25. [PubMed:39079360 ]
Erythropel HC, Jabba SV, Silinski P, Anastas PT, Krishnan-Sarin S, Zimmerman JB, Jordt SE: High Variability in Nicotine Analog Contents, Misleading Labeling, and Artificial Sweetener in New E-Cigarette Products Marketed as "FDA-Exempt". medRxiv [Preprint]. 2024 Apr 22:2024.04.19.24306019. doi: 10.1101/2024.04.19.24306019. [PubMed:38766027 ]
Shil A, Ladeira Faria LM, Walker CA, Chichger H: The artificial sweetener neotame negatively regulates the intestinal epithelium directly through T1R3-signaling and indirectly through pathogenic changes to model gut bacteria. Front Nutr. 2024 Apr 24;11:1366409. doi: 10.3389/fnut.2024.1366409. eCollection 2024. [PubMed:38721028 ]
Gibbons C, Beaulieu K, Almiron-Roig E, Navas-Carretero S, Martinez JA, O'Hara B, O'Connor D, Nazare JA, Le Bail A, Rannou C, Hardman C, Wilton M, Kjolbaek L, Scott C, Moshoyiannis H, Raben A, Harrold JA, Halford JCG, Finlayson G: Acute and two-week effects of neotame, stevia rebaudioside M and sucrose-sweetened biscuits on postprandial appetite and endocrine response in adults with overweight/obesity-a randomised crossover trial from the SWEET consortium. EBioMedicine. 2024 Apr;102:105005. doi: 10.1016/j.ebiom.2024.105005. Epub 2024 Mar 28. [PubMed:38553262 ]
Yang X, Jiang W: Enantioselective Recognition of Functional Organic Molecules in Water by Biomimetic Macrocyclic Hosts. J Am Chem Soc. 2024 Feb 14;146(6):3900-3909. doi: 10.1021/jacs.3c11492. Epub 2024 Jan 31. [PubMed:38294833 ]
Nicoluci IG, da Silva BS, Braga PAC, Bragotto APA: Simultaneous determination of nine high-intensity sweeteners in liquid and powder tabletop sweeteners. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2023 Oct;40(10):1298-1306. doi: 10.1080/19440049.2023.2238836. Epub 2023 Sep 11. [PubMed:37695976 ]
Gvozdic E, Bujagic IM, Durkic T, Grujic S: Untreated wastewater impact and environmental risk assessment of artificial sweeteners in river water and sediments of the Danube River Basin in Serbia. Environ Sci Pollut Res Int. 2023 Jul;30(35):84583-84594. doi: 10.1007/s11356-023-28348-5. Epub 2023 Jun 27. [PubMed:37368207 ]
Zhu K, Chen Y, Yu L, Hou C, Qiao X, Wang T: Determination of neotame in various foods by high-performance liquid chromatography coupled with ultraviolet and mass spectrometric detection. Food Chem. 2023 Aug 1;416:135863. doi: 10.1016/j.foodchem.2023.135863. Epub 2023 Mar 4. [PubMed:36898340 ]
Shen G, Lei S, Li H, Yu Q, Wu G, Shi Y, Xu K, Ren H, Geng J: Occurrence and removal of four artificial sweeteners in wastewater treatment plants of China. Environ Sci Process Impacts. 2023 Jan 25;25(1):75-84. doi: 10.1039/d2em00351a. [PubMed:36476784 ]
Takehara CT, Nicoluci IG, Andrade TFS, Arisseto-Bragotto AP: A comprehensive database of declared high-intensity sweeteners in Brazilian commercial products and updated exposure assessment. Food Res Int. 2022 Nov;161:111899. doi: 10.1016/j.foodres.2022.111899. Epub 2022 Sep 5. [PubMed:36192918 ]

Showing NP-Card for Neotame (NP0337847)

MOL for NP0337847 (Neotame)

3D MOL for NP0337847 (Neotame)

3D SDF for NP0337847 (Neotame)

3D-SDF for NP0337847 (Neotame)

PDB for NP0337847 (Neotame)

3D PDB for NP0337847 (Neotame)

SMILES for NP0337847 (Neotame)

INCHI for NP0337847 (Neotame)

Structure for NP0337847 (Neotame)

3D Structure for NP0337847 (Neotame)