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Plitidepsin

Plitidepsin

Synopsis, Chemistry

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Also known as: Aplidine, Aplidin, 137219-37-5, Dehydrodidemnin b, Y76id234hw, Chebi:90205

Molecular Formula

C₅₇H₈₇N₇O₁₅

Molecular Weight

1110.3 g/mol

InChI Key

UUSZLLQJYRSZIS-LXNNNBEUSA-N

FDA UNII

Y76ID234HW

Plitidepsin is a cyclic depsipeptide isolated from the marine tunicate Aplidium albicans. Plitidepsin displays a broad spectrum of antitumor activities, inducing apoptosis by triggering mitochondrial cytochrome c release, initiating the Fas/DC95, JNK pathway and activating caspase 3 activation. This agent also inhibits elongation factor 1-a, thereby interfering with protein synthesis, and induces G1 arrest and G2 blockade, thereby inhibiting tumor cell growth.

1 2D Structure

Plitidepsin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide

2.1.2 InChI

InChI=1S/C57H87N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-34,36,39-44,46-47,49,66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)/t33-,34-,36+,39-,40-,41-,42+,43-,44-,46+,47-,49-/m0/s1

2.1.3 InChI Key

UUSZLLQJYRSZIS-LXNNNBEUSA-N

2.1.4 Canonical SMILES

CCC(C)C1C(CC(=O)OC(C(=O)C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C(C(=O)OC(C(C(=O)N1)NC(=O)C(CC(C)C)N(C)C(=O)C3CCCN3C(=O)C(=O)C)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O

2.1.5 Isomeric SMILES

CC[C@H](C)[C@@H]1[C@H](CC(=O)O[C@H](C(=O)[C@@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]3CCCN3C(=O)C(=O)C)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O

2.2 Other Identifiers

2.2.1 UNII

Y76ID234HW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aplidin

2. Aplidine

3. Dehydrodidemnin B

2.3.2 Depositor-Supplied Synonyms

1. Aplidine

2. Aplidin

3. 137219-37-5

4. Dehydrodidemnin B

5. Y76id234hw

6. Chebi:90205

7. Plitidepsin (inn)

8. Plitidepsin [inn]

9. (2s)-n-[(2r)-1-[[(3s,6s,8s,12s,13r,16s,17r,20s,23s)-13-[(2s)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-n-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide

10. Plitidepsin [inn:ban]

11. Plitidepsina

12. Plitidepsine

13. Plitidepsium

14. Unii-y76id234hw

15. Aplidine [mi]

16. Plitidepsin [mi]

17. Plitidepsin [mart.]

18. Plitidepsin [who-dd]

19. Didemnin A, N-(1-(1,2-dioxopropyl)-l-prolyl)-

20. Chembl451930

21. 2-9-didemnin B, 2-(1-(1,2-dioxopropyl)-l-proline)-

22. Schembl13413427

23. Gtpl11396

24. (s)-n-((r)-1-(((3s,6r,7s,10r,11s,15s,17s,20s,25as)-10-((s)-sec-butyl)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-1,4,8,13,16,18,21-heptaoxodocosahydro-15h-pyrrolo[2,1-f][1,15]dioxa[4,7,10,20]tetraazacyclotricosin-7-yl)amino)-4-methyl-1-oxopentan-2-yl)-n-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide

25. At23636

26. Db04977

27. Hy-16050

28. Cs-0006129

29. D11032

30. Q4779975

31. Y-100032

32. (2s)-n-[(2r)-1-[[(3s,6s,8s,12s,13r,16s,17r,20s,23s)-13-[(2s)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl) Methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-n-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide

33. 1-(2-oxopropanoyl)-l-prolyl-n-[(3s,6r,7s,10r,11s,15s,17s,20s,25as)-10-[(2s)-butan-2-yl]-11-hydroxy-3-(4-methoxybenzyl)-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,8,13,16,18,21-heptaoxo-15-(propan-2-yl)docosahydro-15h-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin-7-yl]-n(2)-methyl-d-leucinamide

34. 3,6-anhydro(n-((2s,4s)-4-((3s,4r,5s)-3-hydroxy-4-((n-(2-oxopropanoyl)-l-prolyl-n-methyl-d-leucyl-l-threonyl)amino)-5-methylheptanoyloxy)-2,5-dimethyl-3-oxohexanoyl)-l-leucyl-l-prolyl-n,o-dimethyl-l-tyrosine)

35. L-tyrosine, 1-(1,2-dioxopropyl)-l-prolyl-n-methyl-d-leucyl-l-threonyl-(3s,4r,5s)-4-amino-3-hydroxy-5-methylheptanoyl-(2s,4s)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl-l-leucyl-l-prolyl-n,o-dimethyl-, (8-3)-lactone

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₅₇H₈₇N₇O₁₅
Molecular Weight	1110.3 g/mol
XLogP3	5.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	15
Exact Mass	1109.62601509 g/mol
Monoisotopic Mass	1109.62601509 g/mol
Topological Polar Surface Area	285 Å²
Heavy Atom Count	79
Formal Charge	0
Complexity	2200
Isotope Atom Count	0
Defined Atom Stereocenter Count	12
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Intended for the treatment of various forms of cancer.

5 Pharmacology and Biochemistry

5.1 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XX - Other antineoplastic agents

L01XX57 - Plitidepsin

5.2 Metabolism/Metabolites

Hepatic

5.3 Mechanism of Action

Aplidine inhibits the growth and induces apoptosis in MOLT-4 cells through the indirect inhibition of VEGF secretion which blocks the VEGF/VEGFR-1 autocrine loop necessary for the growth of these cells.