5-(1,4-diazepan-1-ylsulfonyl)isoquinoline

ID: ALA541388

Cas Number: 105628-07-7

PubChem CID: 163751

Product Number: F122336, Order Now?

Max Phase: Phase

Molecular Formula: C14H18ClN3O2S

Molecular Weight: 291.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fasudil | Fasudil hydrochloride | Fasudil hydrochloride|105628-07-7|Fasudil HCl|Eril|Fasudil (HA-1077) HCl|5-((1,4-Diazepan-1-yl)sulfonyl)isoquinoline hydrochloride|Fasudil (Hydrochloride)|Fasudil Monohydrochloride|ha-1077|SQ04N8S7BR|Fasudil, Monohydrochloride Salt|DTXSID1045615|MFCD00943198|1-(5-Isoquinolinesulfonyl)homopiperazine hydrochloride|5-(1,4-diazepan-1-ylsulfonyl)isoquinoline hydrochloride|105628-07-7 (HCl)|1H-1,4-Diazepine, hexahydro-1-(5-isoquinolinylsulfonyl)-, monohydrochloride|FaShow More⌵

Canonical SMILES:  Cl.O=S(=O)(c1cccc2cnccc12)N1CCCNCC1

Standard InChI:  InChI=1S/C14H17N3O2S.ClH/c18-20(19,17-9-2-6-15-8-10-17)14-4-1-3-12-11-16-7-5-13(12)14;/h1,3-5,7,11,15H,2,6,8-10H2;1H

Standard InChI Key:  LFVPBERIVUNMGV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    5.0964    2.3885    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    2.9981    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358    3.5978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    2.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6901    3.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373    4.7532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864    6.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571    2.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959    5.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030    6.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  4  7  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  6 11  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 12 15  2  0
 16 17  1  0
 17 18  1  0
 13 19  1  0
 16 19  1  0
 13 20  1  0
 18 21  1  0
 20 21  1  0
M  END

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: 291.38

Molecular Weight (Monoisotopic): 291.1041

AlogP: 1.22

#Rotatable Bonds: 2

Polar Surface Area: 62.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.04

CX LogP: 0.32

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.90

Np Likeness Score: -1.64

References

1. Iwakubo M, Takami A, Okada Y, Kawata T, Tagami Y, Ohashi H, Sato M, Sugiyama T, Fukushima K, Iijima H..  (2007)  Design and synthesis of Rho kinase inhibitors (II).,  15  (1): [PMID:17046269] [10.1016/j.bmc.2006.09.052]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Abbhi V, Saini L, Mishra S, Sethi G, Kumar AP, Piplani P..  (2017)  Design and synthesis of benzimidazole-based Rho kinase inhibitors for the treatment of glaucoma.,  25  (21): [PMID:29033348] [10.1016/j.bmc.2017.09.045]

6. Unpublished dataset, 

7. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

8. 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]

9. 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]

10. 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]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• SARS-CoV-2 Screening Data 2020-21