ID: ALA65

Max Phase: Unknown

Molecular Formula: C20H16N2O4

Molecular Weight: 348.36

Molecule Type: Small molecule

Representations

Synonyms (4): Camptothecin | Camptothecine | Topotecan related compound c | NSC-94600
Synonyms from Alternative Forms(4):

Canonical SMILES:  CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3ccccc3nc2-1

Standard InChI:  InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1

Standard InChI Key:  VSJKWCGYPAHWDS-FQEVSTJZSA-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: No

Properties

Molecular Weight: 348.36

Molecular Weight (Monoisotopic): 348.1110

AlogP: 2.08

#Rotatable Bonds: 1

Polar Surface Area: 81.42

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.71

CX Basic pKa: 3.07

CX LogP: 1.22

CX LogD: 1.22

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: 1.01

References

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484. Tejería A, Pérez-Pertejo Y, Reguera RM, Balaña-Fouce R, Alonso C, González M, Rubiales G, Palacios F..  (2018)  Substituted 1,5-naphthyridine derivatives as novel antileishmanial agents. Synthesis and biological evaluation.,  152  [PMID:29704722] [10.1016/j.ejmech.2018.04.033]

485. Yu Q, Yang H, Zhu TW, Yu LM, Chen JW, Gu LQ, Huang ZS, An LK..  (2018)  Synthesis, cytotoxicity and structure-activity relationship of indolizinoquinolinedione derivatives as DNA topoisomerase IB catalytic inhibitors.,  152  [PMID:29705710] [10.1016/j.ejmech.2018.04.040]

486. Yang CR, Peng B, Cao SL, Ren TT, Jiang W, Wang FC, Li YS, Wang G, Li Z, Xu S, Liao J, Wang H, Li J, Xu X..  (2018)  Synthesis, cytotoxic evaluation and target identification of thieno[2,3-d]pyrimidine derivatives with a dithiocarbamate side chain at C2 position.,  154  [PMID:29843103] [10.1016/j.ejmech.2018.05.028]

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488. Shrestha A, Park S, Jang HJ, Katila P, Shrestha R, Kwon Y, Lee ES..  (2018)  A new phenolic series of indenopyridinone as topoisomerase inhibitors: Design, synthesis, and structure-activity relationships.,  26  (18): [PMID:30262132] [10.1016/j.bmc.2018.09.021]

489. Zhang XR, Wang HW, Tang WL, Zhang Y, Yang H, Hu DX, Ravji A, Marchand C, Kiselev E, Ofori-Atta K, Agama K, Pommier Y, An LK..  (2018)  Discovery, Synthesis, and Evaluation of Oxynitidine Derivatives as Dual Inhibitors of DNA Topoisomerase IB (TOP1) and Tyrosyl-DNA Phosphodiesterase 1 (TDP1), and Potential Antitumor Agents.,  61  (22): [PMID:30336023] [10.1021/acs.jmedchem.8b00639]

490. Colligs V, Hansen SP, Imbri D, Seo EJ, Kadioglu O, Efferth T, Opatz T..  (2017)  Synthesis and biological evaluation of a D-ring-contracted analogue of lamellarin D.,  25  (22): [PMID:28233677] [10.1016/j.bmc.2017.02.005]

491. Shrestha A, Jo H, Kwon Y, Lee ES..  (2018)  Design, synthesis, and structure-activity relationships of new benzofuro[3,2-b]pyridin-7-ols as DNA topoisomerase II inhibitors.,  28  (4): [PMID:29402741] [10.1016/j.bmcl.2018.01.048]

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535. Wang L, Fang K, Cheng J, Li Y, Huang Y, Chen S, Dong G, Wu S, Sheng C..  (2020)  Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer.,  63  (2): [PMID:31880942] [10.1021/acs.jmedchem.9b01626]

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542. Zhang B, Dou Z, Xiong Z, Wang N, He S, Yan X, Jin H..  (2019)  Design, synthesis and biological research of novel N-phenylbenzamide-4-methylamine acridine derivatives as potential topoisomerase I/II and apoptosis-inducing agents.,  29  (23): [PMID:31635931] [10.1016/j.bmcl.2019.126714]

543. 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]

544. 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]

545. 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]

546. 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]

547. Li X, Wu S, Dong G, Chen S, Ma Z, Liu D, Sheng C..  (2020)  Natural Product Evodiamine with Borate Trigger Unit: Discovery of Potent Antitumor Agents against Colon Cancer.,  11  (4): [PMID:32292547] [10.1021/acsmedchemlett.9b00513]

548. Shu B, Yu Q, Hu DX, Che T, Zhang SS, Li D..  (2020)  Synthesis and biological evaluation of novel indole-pyrazoline hybrid derivatives as potential topoisomerase 1 inhibitors.,  30  (4): [PMID:31901379] [10.1016/j.bmcl.2019.126925]

549. Botta L, Filippi S, Zippilli C, Cesarini S, Bizzarri BM, Cirigliano A, Rinaldi T, Paiardini A, Fiorucci D, Saladino R, Negri R, Benedetti P..  (2020)  Artemisinin Derivatives with Antimelanoma Activity Show Inhibitory Effect against Human DNA Topoisomerase 1.,  11  (5): [PMID:32435422] [10.1021/acsmedchemlett.0c00131]

550. Ibric A, Battisti V, Deckardt S, Haller AV, Lee C, Prötsch C, Langer T, Heffeter P, Schueffl HH, Marian B, Haider N..  (2020)  A-ring and E-ring modifications of the cytotoxic alkaloid Luotonin A: Synthesis, computational and biological studies.,  28  (9): [PMID:32201190] [10.1016/j.bmc.2020.115443]

551. Zhang HL, Zhang Y, Yan XL, Xiao LG, Hu DX, Yu Q, An LK..  (2020)  Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.,  28  (11): [PMID:32345458] [10.1016/j.bmc.2020.115527]

552. Xin M, Wei JH, Yang CH, Liang GB, Su D, Ma XL, Zhang Y..  (2020)  Design, synthesis and biological evaluation of 3-nitro-1,8-naphthalimides as potential antitumor agents.,  30  (8): [PMID:32111436] [10.1016/j.bmcl.2020.127051]

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

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561. Laaroussi H,Ding Y,Teng Y,Deschamps P,Vidal M,Yu P,Broussy S.  (2020)  Synthesis of indole inhibitors of silent information regulator 1 (SIRT1), and their evaluation as cytotoxic agents.,  202  [PMID:32711231] [10.1016/j.ejmech.2020.112561]

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570. 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]

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596. Fuertes M, Selas A, Trejo A, Knudsen BR, Palacios F, Alonso C..  (2022)  Synthesis of hybrid phosphorated indenoquinolines and biological evaluation as topoisomerase I inhibitors and antiproliferative agents.,  57  [PMID:34952177] [10.1016/j.bmcl.2021.128517]

597. Kadagathur M, Patra S, Devabattula G, George J, Phanindranath R, Shaikh AS, Sigalapalli DK, Godugu C, Nagesh N, Tangellamudi ND, Shankaraiah N..  (2022)  Design, synthesis of DNA-interactive 4-thiazolidinone-based indolo-/pyrroloazepinone conjugates as potential cytotoxic and topoisomerase I inhibitors.,  238  [PMID:35635947] [10.1016/j.ejmech.2022.114465]

598. Li J, Hu X, Zhang H, Peng Y, Li S, Xiong Y, Jiang W, Wang Z..  (2022)  N-2-(Phenylamino) Benzamide Derivatives as Dual Inhibitors of COX-2 and Topo I Deter Gastrointestinal Cancers via Targeting Inflammation and Tumor Progression.,  65  (15.0): [PMID:35868003] [10.1021/acs.jmedchem.2c00635]

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602. Yang X, Wang ZP, Xiang S, Wang D, Zhao Y, Luo D, Qiu Y, Huang C, Guo J, Dai Y, Zhang SL, He Y..  (2022)  Optimization of the Natural Product Calothrixin A to Discover Novel Dual Topoisomerase I and II Inhibitors with Improved Anticancer Activity.,  65  (11.0): [PMID:35612499] [10.1021/acs.jmedchem.2c00615]

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607. Soltan OM, Shoman ME, Abdel-Aziz SA, Narumi A, Konno H, Abdel-Aziz M..  (2021)  Molecular hybrids: A five-year survey on structures of multiple targeted hybrids of protein kinase inhibitors for cancer therapy.,  225  [PMID:34450497] [10.1016/j.ejmech.2021.113768]

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Source

Source(13):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer
• PubChem BioAssays
• DrugMatrix
• TP-search Transporter Database
• CO-ADD antimicrobial screening data
• SARS-CoV-2 Screening Data 2020-21
• Active Ingredient of a Prodrug
• EUbOPEN Chemogenomic Library
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6
• Cardiff Schistosomiasis Dataset 2023
• EU-OPENSCREEN dataset