ID: ALA10041

Max Phase: Preclinical

Molecular Formula: C26H29NO2

Molecular Weight: 387.52

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC/C(=C(\c1ccccc1)c1ccc(OCCN(C)C)cc1)c1ccc(O)cc1

Standard InChI:  InChI=1S/C26H29NO2/c1-4-25(20-10-14-23(28)15-11-20)26(21-8-6-5-7-9-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-

Standard InChI Key:  DODQJNMQWMSYGS-QPLCGJKRSA-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: 387.52

Molecular Weight (Monoisotopic): 387.2198

AlogP: 5.70

#Rotatable Bonds: 8

Polar Surface Area: 32.70

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.13

CX Basic pKa: 8.52

CX LogP: 5.50

CX LogD: 4.67

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -0.21

References

1. Ruenitz PC, Bagley JR, Mokler CM..  (1982)  Estrogenic and antiestrogenic activity of monophenolic analogues of tamoxifen, (Z)-2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N, N-dimethylethylamine.,  25  (9): [PMID:7131484] [10.1021/jm00351a010]

2. Foster AB, Jarman M, Leung OT, McCague R, Leclercq G, Devleeschouwer N..  (1985)  Hydroxy derivatives of tamoxifen.,  28  (10): [PMID:4045924] [10.1021/jm00148a020]

3. PubChem BioAssay data set, 

4. Liu J, Zheng S, Akerstrom VL, Yuan C, Ma Y, Zhong Q, Zhang C, Zhang Q, Guo S, Ma P, Skripnikova EV, Bratton MR, Pannuti A, Miele L, Wiese TE, Wang G..  (2016)  Fulvestrant-3 Boronic Acid (ZB716): An Orally Bioavailable Selective Estrogen Receptor Downregulator (SERD).,  59  (17): [PMID:27529700] [10.1021/acs.jmedchem.6b00753]

5. Li Y, Zhao J, Gutgesell LM, Shen Z, Ratia K, Dye K, Dubrovskyi O, Zhao H, Huang F, Tonetti DA, Thatcher GRJ, Xiong R..  (2020)  Novel Pyrrolopyridone Bromodomain and Extra-Terminal Motif (BET) Inhibitors Effective in Endocrine-Resistant ER+ Breast Cancer with Acquired Resistance to Fulvestrant and Palbociclib.,  63  (13): [PMID:32453591] [10.1021/acs.jmedchem.0c00456]

6. He M,Ning W,Hu Z,Huang J,Dong C,Zhou HB.  (2020)  Design, synthesis and biological evaluation of novel dual-acting modulators targeting both estrogen receptor α (ERα) and lysine-specific demethylase 1 (LSD1) for treatment of breast cancer.,  195  [PMID:32283297] [10.1016/j.ejmech.2020.112281]

7. Bai C, Wu S, Ren S, Zhu M, Luo G, Xiang H..  (2021)  Benzothiophene derivatives as selective estrogen receptor covalent antagonists: Design, synthesis and anti-ERα activities.,  47  [PMID:34509864] [10.1016/j.bmc.2021.116395]

8. Bai C, Ren S, Wu S, Zhu M, Luo G, Xiang H..  (2021)  Design and synthesis of novel benzothiophene analogs as selective estrogen receptor covalent antagonists against breast cancer.,  221  [PMID:34022716] [10.1016/j.ejmech.2021.113543]

9. Kurtanović N, Tomašević N, Matić S, Mitrović MM, Kostić DA, Sabatino M, Antonini L, Ragno R, Mladenović M..  (2022)  Human estrogen receptor α antagonists, part 2: Synthesis driven by rational design, in vitro antiproliferative, and in vivo anticancer evaluation of innovative coumarin-related antiestrogens as breast cancer suppressants.,  227  [PMID:34710747] [10.1016/j.ejmech.2021.113869]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays