(R,E)-2-acetyl-6-(2-(2-(4-bromobenzyliden)hydrazinyl)thiazol-4-yl)-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one

ID: ALA4438274

Chembl Id: CHEMBL4438274

PubChem CID: 139593986

Max Phase: Preclinical

Molecular Formula: C26H20BrN3O6S

Molecular Weight: 582.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)C1=C(O)C=C2Oc3c(-c4csc(N/N=C/c5ccc(Br)cc5)n4)c(O)c(C)c(O)c3[C@@]2(C)C1=O

Standard InChI:  InChI=1S/C26H20BrN3O6S/c1-11-21(33)19(15-10-37-25(29-15)30-28-9-13-4-6-14(27)7-5-13)23-20(22(11)34)26(3)17(36-23)8-16(32)18(12(2)31)24(26)35/h4-10,32-34H,1-3H3,(H,29,30)/b28-9+/t26-/m0/s1

Standard InChI Key:  JSRXTHWZVFGCJR-CXEQAMIMSA-N

Alternative Forms

1. Parent:

   

   ALA4438274

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 582.43

Molecular Weight (Monoisotopic): 581.0256

AlogP: 5.26

#Rotatable Bonds: 5

Polar Surface Area: 141.34

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.59

CX Basic pKa: 4.81

CX LogP: 4.27

CX LogD: 2.20

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.18

Np Likeness Score: 0.24

References

1. Zakharenko AL, Luzina OA, Sokolov DN, Kaledin VI, Nikolin VP, Popova NA, Patel J, Zakharova OD, Chepanova AA, Zafar A, Reynisson J, Leung E, Leung IKH, Volcho KP, Salakhutdinov NF, Lavrik OI..  (2019)  Novel tyrosyl-DNA phosphodiesterase 1 inhibitors enhance the therapeutic impact of topoteсan on in vivo tumor models.,  161  [PMID:30396105] [10.1016/j.ejmech.2018.10.055]

2. Ivankin DI, Dyrkheeva NS, Zakharenko AL, Ilina ES, Zarkov TO, Reynisson J, Luzina OA, Volcho KP, Salakhutdinov NF, Lavrik OI..  (2022)  Monoterpene substituted thiazolidin-4-ones as novel TDP1 inhibitors: Synthesis, biological evaluation and docking.,  73  [PMID:35907608] [10.1016/j.bmcl.2022.128909]

Source

Source(1):

• Scientific Literature