ID: ALA238071

Max Phase: Approved

Molecular Formula: C43H55N5O7

Molecular Weight: 753.94

Molecule Type: Small molecule

Representations

Synonyms (3): Vindesine | COMPOUND 112531 | COMPOUND-112531
Synonyms from Alternative Forms(3):

Canonical SMILES:  CC[C@]1(O)C[C@@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@H]3[C@@](O)(C(N)=O)[C@H](O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1

Standard InChI:  InChI=1S/C43H55N5O7/c1-6-39(52)21-25-22-42(38(51)55-5,33-27(13-17-47(23-25)24-39)26-11-8-9-12-30(26)45-33)29-19-28-31(20-32(29)54-4)46(3)35-41(28)15-18-48-16-10-14-40(7-2,34(41)48)36(49)43(35,53)37(44)50/h8-12,14,19-20,25,34-36,45,49,52-53H,6-7,13,15-18,21-24H2,1-5H3,(H2,44,50)/t25-,34-,35+,36+,39-,40+,41+,42-,43-/m0/s1

Standard InChI Key:  HHJUWIANJFBDHT-ZVTSDNJWSA-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: 753.94

Molecular Weight (Monoisotopic): 753.4101

AlogP: 2.73

#Rotatable Bonds: 6

Polar Surface Area: 164.82

Molecular Species: BASE

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.34

CX Basic pKa: 8.68

CX LogP: 2.79

CX LogD: 0.82

Aromatic Rings: 3

Heavy Atoms: 55

QED Weighted: 0.19

Np Likeness Score: 1.43

References

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5. Zuse A, Schmidt P, Baasner S, Böhm KJ, Müller K, Gerlach M, Günther EG, Unger E, Prinz H..  (2006)  9-Benzylidene-naphtho[2,3-b]thiophen-4-ones as novel antimicrotubule agents-synthesis, antiproliferative activity, and inhibition of tubulin polymerization.,  49  (26): [PMID:17181164] [10.1021/jm0605031]

6. Sasaki H, Haraguchi Y, Itotani M, Kuroda H, Hashizume H, Tomishige T, Kawasaki M, Matsumoto M, Komatsu M, Tsubouchi H..  (2006)  Synthesis and antituberculosis activity of a novel series of optically active 6-nitro-2,3-dihydroimidazo[2,1-b]oxazoles.,  49  (26): [PMID:17181168] [10.1021/jm060957y]

7. Zuse A, Schmidt P, Baasner S, Böhm KJ, Müller K, Gerlach M, Günther EG, Unger E, Prinz H..  (2007)  Sulfonate derivatives of naphtho[2,3-b]thiophen-4(9H)-one and 9(10H)-anthracenone as highly active antimicrotubule agents. Synthesis, antiproliferative activity, and inhibition of tubulin polymerization.,  50  (24): [PMID:17973361] [10.1021/jm0708984]

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11. Nickel HC, Schmidt P, Böhm KJ, Baasner S, Müller K, Gerlach M, Unger E, Günther EG, Prinz H..  (2010)  Synthesis, antiproliferative activity and inhibition of tubulin polymerization by 1,5- and 1,8-disubstituted 10H-anthracen-9-ones bearing a 10-benzylidene or 10-(2-oxo-2-phenylethylidene) moiety.,  45  (8): [PMID:20537765] [10.1016/j.ejmech.2010.04.032]

12. Kularatne SA, Venkatesh C, Santhapuram HK, Wang K, Vaitilingam B, Henne WA, Low PS..  (2010)  Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs.,  53  (21): [PMID:20936874] [10.1021/jm100729b]

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

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22. Unpublished dataset, 

23. 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]

24. 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]

25. 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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Source

Source(7):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data