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Chemistry

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Also known as: 125973-56-0, Tac-101, Am 555s, Amsilarotene [inn], Am555s,tac-101, 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]benzoic acid

Molecular Formula

C₂₀H₂₇NO₃Si₂

Molecular Weight

385.6 g/mol

InChI Key

VVTNSTLJOVCBDL-UHFFFAOYSA-N

FDA UNII

Q1418F39MH

Amsilarotene is a retinobenzoic acid with potential antineoplastic activity. Amsilarotene inhibits retinoblastoma-gene product (RB) phosphorylation and increases the presence of 2 cyclin-dependent kinase (CDK) inhibitors, resulting in cell cycle arrest. This agent also causes a cytotoxic decline in cyclin A and thymidylate synthase expression.

1 2D Structure

Tac 101

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[[3,5-bis(trimethylsilyl)benzoyl]amino]benzoic acid

2.1.2 InChI

InChI=1S/C20H27NO3Si2/c1-25(2,3)17-11-15(12-18(13-17)26(4,5)6)19(22)21-16-9-7-14(8-10-16)20(23)24/h7-13H,1-6H3,(H,21,22)(H,23,24)

2.1.3 InChI Key

VVTNSTLJOVCBDL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C[Si](C)(C)C1=CC(=CC(=C1)C(=O)NC2=CC=C(C=C2)C(=O)O)[Si](C)(C)C

2.2 Other Identifiers

2.2.1 UNII

Q1418F39MH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(3,5-bis(trimethylsilyl)benzamido)benzoic Acid

2. Am 555s

3. Am-555s

4. Am555s

5. Tac 101

6. Tac-101

2.3.2 Depositor-Supplied Synonyms

1. 125973-56-0

2. Tac-101

3. Am 555s

4. Amsilarotene [inn]

5. Am555s,tac-101

6. 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]benzoic Acid

7. Amsilarotene; Tac 101

8. Q1418f39mh

9. 4-[3,5-bis(trimethylsilyl) Benzamido] Benzoic Acid

10. Benzoic Acid, 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-

11. Am-555s

12. Tac 101

13. 4-(3,5-bis(trimethylsilyl)benzamido)benzoic Acid

14. Benzoic Acid, 4-((3,5-bis(trimethylsilyl)benzoyl)amino)-

15. Unii-q1418f39mh

16. Ccris 9419

17. 4-(3,5-bis(trimethylsilyl)benzamido) Benzoic Acid

18. Amsilarotene [who-dd]

19. Chembl32994

20. Schembl1133175

21. Dtxsid90155013

22. Ex-a128

23. Bcp06502

24. Akos032947226

25. Zinc169746726

26. Ac-36797

27. Da-13333

28. Hy-14653

29. Cs-0003504

30. Ft-0769431

31. A13122

32. Q27286879

33. 5-(4-methylphenyl)furan-2-carboxylicacidmethylester

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₇NO₃Si₂
Molecular Weight	385.6 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	385.15294679 g/mol
Monoisotopic Mass	385.15294679 g/mol
Topological Polar Surface Area	66.4 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	494
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1