ID: ALA46102

Max Phase: Unknown

Molecular Formula: C19H28N2O4

Molecular Weight: 348.44

Molecule Type: Small molecule

Representations

Synonyms (1): Pifatidine
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)OCC(=O)NCCCOc1cccc(CN2CCCCC2)c1

Standard InChI:  InChI=1S/C19H28N2O4/c1-16(22)25-15-19(23)20-9-6-12-24-18-8-5-7-17(13-18)14-21-10-3-2-4-11-21/h5,7-8,13H,2-4,6,9-12,14-15H2,1H3,(H,20,23)

Standard InChI Key:  SMTZFNFIKUPEJC-UHFFFAOYSA-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: Yes

Properties

Molecular Weight: 348.44

Molecular Weight (Monoisotopic): 348.2049

AlogP: 2.12

#Rotatable Bonds: 9

Polar Surface Area: 67.87

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.74

CX LogP: 1.31

CX LogD: -0.05

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.55

Np Likeness Score: -1.29

References

1. Li L, Kracht J, Peng S, Bernhardt G, Elz S, Buschauer A..  (2003)  Synthesis and pharmacological activity of fluorescent histamine H2 receptor antagonists related to potentidine.,  13  (10): [PMID:12729649] [10.1016/s0960-894x(03)00235-x]

2. Kojima K, Nakajima K, Kurata H, Tabata K, Utsui Y.  (1996)  Synthesis of a piperidinomethylthiophene derivative as H2-antagonist with inhibitory activity against Helicobacter pylori,  6  (15): [10.1016/0960-894X(96)00313-7]

3. Katsura Y, Inoue Y, Tomishi T, Ishikawa H, Takasugi H..  (1994)  Studies on antiulcer drugs. 7. 2-Guanidino-4-pyridylthiazoles as histamine H2-receptor antagonists with potent gastroprotective effects against nonsteroidal antiinflammatory drug-induced injury.,  37  (1): [PMID:7904648] [10.1021/jm00027a007]

4. Morphy R, Rankovic Z..  (2005)  Designed multiple ligands. An emerging drug discovery paradigm.,  48  (21): [PMID:16220969] [10.1021/jm058225d]

5. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

6. 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]

7. 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]

8. 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]

9. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

10. Zimmermann M, Zimmermann-Kogadeeva M, Wegmann R, Goodman AL..  (2019)  Mapping human microbiome drug metabolism by gut bacteria and their genes.,  570  (7762): [PMID:31158845] [10.1038/s41586-019-1291-3]

Source

Source(4):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6
• Zimmerman Lab Biotransformation data Dec 2023