ID: ALA387152

Max Phase: Preclinical

Molecular Formula: C27H33BrO5S

Molecular Weight: 549.53

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-88915
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2C(=O)COS(=O)(=O)c1ccc(Br)cc1

Standard InChI:  InChI=1S/C27H33BrO5S/c1-26-13-11-19(29)15-17(26)3-8-21-22-9-10-24(27(22,2)14-12-23(21)26)25(30)16-33-34(31,32)20-6-4-18(28)5-7-20/h4-7,15,21-24H,3,8-14,16H2,1-2H3/t21-,22-,23-,24+,26-,27-/m0/s1

Standard InChI Key:  ZQNARVKYKGBJES-YNHSGCSHSA-N

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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 549.53

Molecular Weight (Monoisotopic): 548.1232

AlogP: 5.87

#Rotatable Bonds: 5

Polar Surface Area: 77.51

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa:

CX LogP: 6.15

CX LogD: 6.15

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: 1.11

References

1. Li C, Xu L, Wolan DW, Wilson IA, Olson AJ..  (2004)  Virtual screening of human 5-aminoimidazole-4-carboxamide ribonucleotide transformylase against the NCI diversity set by use of AutoDock to identify novel nonfolate inhibitors.,  47  (27): [PMID:15615517] [10.1021/jm049504o]

2. Taylor CM, Barda Y, Kisselev OG, Marshall GR..  (2008)  Modulating G-protein coupled receptor/G-protein signal transduction by small molecules suggested by virtual screening.,  51  (17): [PMID:18707087] [10.1021/jm800326q]

3. Schlicker C, Rauch A, Hess KC, Kachholz B, Levin LR, Buck J, Steegborn C..  (2008)  Structure-based development of novel adenylyl cyclase inhibitors.,  51  (15): [PMID:18630896] [10.1021/jm800481q]

4. Weidlich IE, Dexheimer T, Marchand C, Antony S, Pommier Y, Nicklaus MC..  (2010)  Inhibitors of human tyrosyl-DNA phospodiesterase (hTdp1) developed by virtual screening using ligand-based pharmacophores.,  18  (1): [PMID:19963390] [10.1016/j.bmc.2009.11.008]

5. Dexheimer TS, Gediya LK, Stephen AG, Weidlich I, Antony S, Marchand C, Interthal H, Nicklaus M, Fisher RJ, Njar VC, Pommier Y..  (2009)  4-Pregnen-21-ol-3,20-dione-21-(4-bromobenzenesulfonate) (NSC 88915) and related novel steroid derivatives as tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors.,  52  (22): [PMID:19883083] [10.1021/jm901061s]

6. Sierecki E, Sinko W, McCammon JA, Newton AC..  (2010)  Discovery of small molecule inhibitors of the PH domain leucine-rich repeat protein phosphatase (PHLPP) by chemical and virtual screening.,  53  (19): [PMID:20836557] [10.1021/jm100331d]

7. PubChem BioAssay data set, 

8. Nguyen TX, Morrell A, Conda-Sheridan M, Marchand C, Agama K, Bermingham A, Stephen AG, Chergui A, Naumova A, Fisher R, O'Keefe BR, Pommier Y, Cushman M..  (2012)  Synthesis and biological evaluation of the first dual tyrosyl-DNA phosphodiesterase I (Tdp1)-topoisomerase I (Top1) inhibitors.,  55  (9): [PMID:22536944] [10.1021/jm300335n]

9. Conda-Sheridan M, Reddy PV, Morrell A, Cobb BT, Marchand C, Agama K, Chergui A, Renaud A, Stephen AG, Bindu LK, Pommier Y, Cushman M..  (2013)  Synthesis and biological evaluation of indenoisoquinolines that inhibit both tyrosyl-DNA phosphodiesterase I (Tdp1) and topoisomerase I (Top1).,  56  (1): [PMID:23259865] [10.1021/jm3014458]

10. Capranico G, Marinello J, Chillemi G..  (2017)  Type I DNA Topoisomerases.,  60  (6): [PMID:28072526] [10.1021/acs.jmedchem.6b00966]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays