[2-(4-Benzyl-phenoxy)-ethyl]-diethyl-amine

ID: ALA26424

Cas Number: 98774-23-3

PubChem CID: 108092

Product Number: D350282, Order Now?

Max Phase: Phase

Molecular Formula: C19H25NO

Molecular Weight: 283.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tesmilifene | Tesmilifene|98774-23-3|2-(4-benzylphenoxy)-N,N-diethylethanamine|DPPE|Tesmilifene [INN]|N,N-Diethyl-2-((4-phenylmethyl)phenoxy)ethanamine|Depmpe|CHEMBL26424|I43T3ID6G2|DTXSID1045661|n,n-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine|N,N-DIETHYL-2-[4-BENZYLPHENOXY]ETHANAMINE|Ethanamine, N,N-diethyl-2-(4-(phenylmethyl)phenoxy)-|NCGC00024762-02|DTXCID9025661|UNII-I43T3ID6G2|CAS-98774-23-3|Ethanamine, N,N-diethyl-2-[4-(phenylmethyl)phenoxy]-|YMB1002|Tocris-0743|TESMILIFENE [MI]|2-((alphShow More⌵

Synonyms from Alternative Forms(8): Tesmilifene hcl | Tesmilifene hydrochloride | BMS-217380-01 | BMY-33419 | DPP-E | DPPE | NSC-741196 | NSC-76285

Canonical SMILES:  CCN(CC)CCOc1ccc(Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C19H25NO/c1-3-20(4-2)14-15-21-19-12-10-18(11-13-19)16-17-8-6-5-7-9-17/h5-13H,3-4,14-16H2,1-2H3

Standard InChI Key:  NFIXBCVWIPOYCD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.1208   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    0.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3000    0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500    0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 12  1  0
  4  8  1  0
  5  1  2  0
  6  1  1  0
  7  5  1  0
  8  6  2  0
  9  2  1  0
 10  4  1  0
 11 10  1  0
 12 11  1  0
 13  3  1  0
 14  3  1  0
 15  9  1  0
 16  9  2  0
 17 13  1  0
 18 14  1  0
 19 16  1  0
 20 15  2  0
 21 19  2  0
  7  4  2  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA26424

   DPPE Fumarate

2. Alternative Forms:

   

   ALA26424

   TESMILIFENE HYDROCHLORIDE

Molecule Features

Natural Product: No

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

Calculated Properties

Molecular Weight: 283.41

Molecular Weight (Monoisotopic): 283.1936

AlogP: 4.00

#Rotatable Bonds: 8

Polar Surface Area: 12.47

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.33

CX LogP: 4.64

CX LogD: 2.72

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: -0.91

References

1. Teo CC, Kon OL, Sim KY, Ng SC..  (1992)  Synthesis of 2-(p-chlorobenzyl)-3-aryl-6-methoxybenzofurans as selective ligands for antiestrogen-binding sites. Effects on cell proliferation and cholesterol synthesis.,  35  (8): [PMID:1573630] [10.1021/jm00086a002]

2. Penning TD, Chandrakumar NS, Chen BB, Chen HY, Desai BN, Djuric SW, Docter SH, Gasiecki AF, Haack RA, Miyashiro JM, Russell MA, Yu SS, Corley DG, Durley RC, Kilpatrick BF, Parnas BL, Askonas LJ, Gierse JK, Harding EI, Highkin MK, Kachur JF, Kim SH, Krivi GG, Villani-Price D, Pyla EY, Smith WG..  (2000)  Structure-activity relationship studies on 1-[2-(4-Phenylphenoxy)ethyl]pyrrolidine (SC-22716), a potent inhibitor of leukotriene A(4) (LTA(4)) hydrolase.,  43  (4): [PMID:10691697] [10.1021/jm990496z]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

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

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. Unpublished dataset, 

10. 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]

11. 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]

12. 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]

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

14. 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(7):

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