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Technical details about Plitidepsin, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: Aplidin, Aplidine, Dehydrodidemnin b, Plitidepsina, Plitidepsine, Plitidepsium
Molecular Formula
C57H87N7O15
Molecular Weight
1110.357  g/mol
InChI Key
UUSZLLQJYRSZIS-LXNNNBEUSA-N
FDA UNII
Y76ID234HW

Aplidine is a compound found in tunicates which shows promise in shrinking tumors in pancreatic, stomach, bladder, and prostate cancers. The specific marine organism is Aplidium albicans. Aplidine consists of peptide molecules. In addition to the cancers mentioned above it is also under consideration as a treatment for some types of leukemia. [Wikipedia]
1 2D Structure

2D Structure

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 Depositor-Supplied Synonyms

1. Aplidin

2. Aplidine

3. Dehydrodidemnin B

4. Plitidepsina

5. Plitidepsine

6. Plitidepsium

7. Unii-y76id234hw

8. 137219-37-5

9. Y76id234hw

10. Chebi:90205

11. Plitidepsin [inn:ban]

12. Dihydrodidemnin B

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

14. Chembl451930

15. 2-9-didemnin B, 2-(1-(1,2-dioxopropyl)-l-proline)-

16. Schembl13413427

17. Akos030230703

18. Db04977

19. Z-3094

20. Y-100032

21. 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

22. 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 Weight 1110.357 g/mol
Molecular Formula C57H87N7O15
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count15
Rotatable Bond Count15
Exact Mass1109.626 g/mol
Monoisotopic Mass1109.626 g/mol
Topological Polar Surface Area285 A^2
Heavy Atom Count79
Formal Charge0
Complexity2200
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Intended for the treatment of various forms of cancer.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 Metabolism/Metabolites

Metabolism

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.