ID: ALA171679

Max Phase: Phase

Molecular Formula: C14H18N2O5

Molecular Weight: 294.31

Molecule Type: Small molecule

Representations

Synonyms (13): Aspartame | Aspartame (e951) | Ins no.951 | Ins-951 | Methyl aspartylphenylalanate | Nutrasweet | Pal sweet | Sladex | Zero-cal | APM | E-951 | NSC-758953 | SC-18862
Synonyms from Alternative Forms(13):

Canonical SMILES:  COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CC(=O)O

Standard 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

Standard InChI Key:  IAOZJIPTCAWIRG-QWRGUYRKSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 294.31

Molecular Weight (Monoisotopic): 294.1216

AlogP: -0.31

#Rotatable Bonds: 7

Polar Surface Area: 118.72

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.53

CX Basic pKa: 8.53

CX LogP: -2.22

CX LogD: -2.25

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.59

Np Likeness Score: 0.26

References

1. Walters DE, Hinds RM..  (1994)  Genetically evolved receptor models: a computational approach to construction of receptor models.,  37  (16): [PMID:8057298] [10.1021/jm00042a006]

2. Kawai M, Nyfeler R, Berman JM, Goodman M..  (1982)  Peptide sweeteners. 5. Side-chain homologues relating zwitterionic and trifluoroacetylated amino acid anilide and dipeptide sweeteners.,  25  (4): [PMID:7069717] [10.1021/jm00346a013]

3. Kawai M, Chorev M, Marin-Rose J, Goodman M..  (1980)  Peptide sweeteners. 4. Hydroxy and methoxy substitution of the aromatic ring in L-aspartyl-L-phenylalanine methyl ester. Structure-taste relationships.,  23  (4): [PMID:7381840] [10.1021/jm00178a013]

4. Kawai M, Chorev M, Marin-Rose J, Goodman M..  (1980)  Peptide sweeteners. 4. Hydroxy and methoxy substitution of the aromatic ring in L-aspartyl-L-phenylalanine methyl ester. Structure-taste relationships.,  23  (4): [PMID:7381840] [10.1021/jm00178a013]

5. Iwamura H..  (1981)  Structure--sweetness relationship of L-aspartyl dipeptide analogues. A receptor site topology.,  24  (5): [PMID:7241515] [10.1021/jm00137a018]

6. Miyashita Y, Takahashi Y, Takayama C, Sumi K, Nakatsuka K, Ohkubo T, Abe H, Sasaki S..  (1986)  Structure-taste correlation of L-aspartyl dipeptides using SIMCA method.,  29  (6): [PMID:3712380] [10.1021/jm00156a006]

7. DuBois GE, Stephenson RA..  (1985)  Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties.,  28  (1): [PMID:3965718] [10.1021/jm00379a017]

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H..  (1999)  Transport of ochratoxin A by renal multispecific organic anion transporter 1.,  289  (1): [PMID:10336520]

12. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H..  (2001)  Characterization of ochratoxin A transport by human organic anion transporters.,  69  (1): [PMID:11669456] [10.1016/s0024-3205(01)01296-6]

13. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H..  (2002)  Role of human organic anion transporter 4 in the transport of ochratoxin A.,  1590  (1): [PMID:12063169] [10.1016/s0167-4889(02)00187-8]

14. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

15. Settimo L, Bellman K, Knegtel RM..  (2013)  Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.,  [PMID:24249037] [10.1007/s11095-013-1232-z]

16. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

17. PubChem BioAssay data set, 

18. PubChem BioAssay data set, 

19. PubChem BioAssay data set, 

20. PubChem BioAssay data set, 

21.  (2008)  T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds, 

22. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

23. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

24.  (2012)  Methods to identify modulators, 

25. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

26. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

27. Min W, Hou Z, Zhang F, Xie S, Yuan K, Dong H, Wang L, Qi L, Luo C, Ding H, Yang P..  (2020)  Computational discovery and biological evaluation of novel inhibitors targeting histone-lysine N-methyltransferase SET7.,  28  (7): [PMID:32088124] [10.1016/j.bmc.2020.115372]

28. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

29. Unpublished dataset, 

30. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• TP-search Transporter Database
• Patent Bioactivity Data
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6