1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea

ID: ALA12948

Chembl Id: CHEMBL12948

Max Phase: Phase

Molecular Formula: C10H18ClN3O2

Molecular Weight: 247.73

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Methyl lomustine | Semustine | ICIG 1110 | ICIG-1110 | METHYL-CCNU | NSC-758471

Canonical SMILES:  CC1CCC(NC(=O)N(CCCl)N=O)CC1

Standard InChI:  InChI=1S/C10H18ClN3O2/c1-8-2-4-9(5-3-8)12-10(15)14(13-16)7-6-11/h8-9H,2-7H2,1H3,(H,12,15)

Standard InChI Key:  FVLVBPDQNARYJU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA12948

   SEMUSTINE

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

Calculated Properties

Molecular Weight: 247.73

Molecular Weight (Monoisotopic): 247.1088

AlogP: 2.50

#Rotatable Bonds: 4

Polar Surface Area: 61.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: 2.44

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.47

Np Likeness Score: -0.54

References

1. McElhinney RS, McCormick JE, Bibby MC, Double JA, Radacic M, Dumont P..  (1996)  Nucleoside analogs. 14. The synthesis of antitumor activity in mice of molecular combinations of 5-fluorouracil and N-(2-Chloroethyl)-N-nitrosourea moieties separated by a three-carbon chain.,  39  (7): [PMID:8691470] [10.1021/jm9507237]

2. Crider AM, Lamey R, Floss HG, Cassady JM, Bradner WJ..  (1980)  Synthesis of nitrosourea derivatives of pyridine and piperidine as potential anticancer agents.,  23  (8): [PMID:7401113] [10.1021/jm00182a007]

3. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

7. Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G..  (1999)  Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells.,  274  (1): [PMID:9880528] [10.1074/jbc.274.3.1519]

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

9. PubChem BioAssay data set, 

10. 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]

11. WHO Anatomical Therapeutic Chemical Classification, 

12. Unpublished dataset, 

13. 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]

14. 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]

15. 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]

16. 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
• DrugMatrix
• TP-search Transporter Database
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6