ID: ALA108335

Max Phase: Phase

Molecular Formula: C47H58N12O6

Molecular Weight: 887.06

Molecule Type: Protein

Representations

Synonyms (4): Examorelin | Hexarelin | EP-23905 | MF-6003
Synonyms from Alternative Forms(4):

Canonical SMILES:  Cc1[nH]c2ccccc2c1C[C@@H](NC(=O)[C@@H](N)Cc1c[nH]cn1)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@H](Cc1ccccc1)C(=O)N[C@@H](CCCCN)C(N)=O

Standard InChI:  InChI=1S/C47H58N12O6/c1-27-34(33-15-7-9-17-37(33)54-27)23-41(58-44(62)35(49)22-31-25-51-26-53-31)45(63)55-28(2)43(61)57-40(21-30-24-52-36-16-8-6-14-32(30)36)47(65)59-39(20-29-12-4-3-5-13-29)46(64)56-38(42(50)60)18-10-11-19-48/h3-9,12-17,24-26,28,35,38-41,52,54H,10-11,18-23,48-49H2,1-2H3,(H2,50,60)(H,51,53)(H,55,63)(H,56,64)(H,57,61)(H,58,62)(H,59,65)/t28-,35-,38-,39+,40-,41+/m0/s1

Standard InChI Key:  RVWNMGKSNGWLOL-GIIHNPQRSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 887.06

Molecular Weight (Monoisotopic): 886.4602

AlogP: 1.34

#Rotatable Bonds: 23

Polar Surface Area: 300.89

Molecular Species: BASE

HBA: 9

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 14

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.76

CX Basic pKa: 10.19

CX LogP: 0.73

CX LogD: -2.26

Aromatic Rings: 6

Heavy Atoms: 65

QED Weighted: 0.04

Np Likeness Score: -0.05

References

1. Guerlavais V, Boeglin D, Mousseaux D, Oiry C, Heitz A, Deghenghi R, Locatelli V, Torsello A, Ghé C, Catapano F, Muccioli G, Galleyrand JC, Fehrentz JA, Martinez J..  (2003)  New active series of growth hormone secretagogues.,  46  (7): [PMID:12646029] [10.1021/jm020985q]

2. Nargund RP, Patchett AA, Bach MA, Murphy MG, Smith RG..  (1998)  Peptidomimetic growth hormone secretagogues. Design considerations and therapeutic potential.,  41  (17): [PMID:9703459] [10.1021/jm970342o]

3. Demange L, Boeglin D, Moulin A, Mousseaux D, Ryan J, Bergé G, Gagne D, Heitz A, Perrissoud D, Locatelli V, Torsello A, Galleyrand JC, Fehrentz JA, Martinez J..  (2007)  Synthesis and pharmacological in vitro and in vivo evaluations of novel triazole derivatives as ligands of the ghrelin receptor. 1.,  50  (8): [PMID:17375904] [10.1021/jm070024h]

4. Moulin A, Demange L, Ryan J, Mousseaux D, Sanchez P, Bergé G, Gagne D, Perrissoud D, Locatelli V, Torsello A, Galleyrand JC, Fehrentz JA, Martinez J..  (2008)  New trisubstituted 1,2,4-triazole derivatives as potent ghrelin receptor antagonists. 3. Synthesis and pharmacological in vitro and in vivo evaluations.,  51  (3): [PMID:18193826] [10.1021/jm701292s]

5. Wang YX, Wang L, Xu YN, Li YH, Jiang JD, Si SY, Li YB, Ren G, Shan YQ, Hong B, Song DQ..  (2011)  Synthesis and structure-activity relationship of N-(2-arylethyl) isoquinoline derivatives as human scavenger receptor CD36 antagonists.,  46  (4): [PMID:21295889] [10.1016/j.ejmech.2011.01.022]

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

7. Proulx C, Picard É, Boeglin D, Pohankova P, Chemtob S, Ong H, Lubell WD..  (2012)  Azapeptide analogues of the growth hormone releasing peptide 6 as cluster of differentiation 36 receptor ligands with reduced affinity for the growth hormone secretagogue receptor 1a.,  55  (14): [PMID:22712585] [10.1021/jm300557t]

8. McCoull W, Barton P, Brown AJ, Bowker SS, Cameron J, Clarke DS, Davies RD, Dossetter AG, Ertan A, Fenwick M, Green C, Holmes JL, Martin N, Masters D, Moore JE, Newcombe NJ, Newton C, Pointon H, Robb GR, Sheldon C, Stokes S, Morgan D..  (2014)  Identification, optimization, and pharmacology of acylurea GHS-R1a inverse agonists.,  57  (14): [PMID:24967667] [10.1021/jm500610n]

9. Chignen Possi K, Mulumba M, Omri S, Garcia-Ramos Y, Tahiri H, Chemtob S, Ong H, Lubell WD..  (2017)  Influences of Histidine-1 and Azaphenylalanine-4 on the Affinity, Anti-inflammatory, and Antiangiogenic Activities of Azapeptide Cluster of Differentiation 36 Receptor Modulators.,  60  (22): [PMID:29028172] [10.1021/acs.jmedchem.7b01209]

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.  (2018)  Novel cyclic peptides and uses thereof, 

12.  (2013)  Azapeptides as cd36 binding compounds, 

13. 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]

14. 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]

15. 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]

16. Bukhari SNA..  (2022)  An insight into the multifunctional role of ghrelin and structure activity relationship studies of ghrelin receptor ligands with clinical trials.,  235  [PMID:35344905] [10.1016/j.ejmech.2022.114308]

Source

Source(5):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• Patent Bioactivity Data
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6