aplidin

Also known as Dehydrodidemnin B, plitidepsina, Plitidepsin, plitidepsium, plitidepsine

Plitidepsin, also known as dehydrodidemnin B and sold under the brand name Aplidin, is a chemical compound extracted from the ascidian Aplidium albicans.

Chemical data

Formula: C57H87N7O15
Molecular weight: 1110.3 g/mol
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
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
InChIKey: UUSZLLQJYRSZIS-LXNNNBEUSA-N
XLogP: 5.7
Polar surface area: 285 Å²
H-bond donors: 4
H-bond acceptors: 15
Formal charge: 0

via PubChem

Research

220 papers

Aplidin PharmaMar.IDrugs : the investigational drugs journal · 2003
Aplidin (plitidepsin) is a novel anti-myeloma agent with potent anti-resorptive activity mediated by direct effects on osteoclasts.Oncotarget · 2019
Population pharmacokinetics meta-analysis of plitidepsin (Aplidin) in cancer subjects.Cancer chemotherapy and pharmacology · 2009
Aplidin, a marine organism-derived compound with potent antimyeloma activity in vitro and in vivo.Cancer research · 2008
Aplidin induces JNK-dependent apoptosis in human breast cancer cells via alteration of glutathione homeostasis, Rac1 GTPase activation, and MKP-1 phosphatase downregulation.Cell death and differentiation · 2006

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 1109.626015084

Show 4 more facts

isomeric SMILES: O=C([C@@H](NC([C@@H](C)C([C@@H](OC(C[C@H](O)[C@H](NC([C@@H](NC([C@H](N(C([C@H]1N(C(C(C)=O)=O)CCC1)=O)C)CC(C)C)=O)[C@@H](C)OC([C@H](CC2=CC=C(OC)C=C2)N3C)=O)=O)[C@@H](C)CC)=O)C(C)C)=O)=O)CC(C)C)N4[C@H](C3=O)CCC4
found in taxon: Aplidium albicans
chemical formula: C₅₇H₈₇N₇O₁₅
canonical SMILES: O=C1OC(C(=O)C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C)C(C(=O)OC(C)C(NC(=O)C(N(C(=O)C3N(C(=O)C(=O)C)CCC3)C)CC(C)C)C(=O)NC(C(O)C1)C(C)CC)CC4=CC=C(OC)C=C4)CC(C)C)C)C(C)C

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~3 min read

Encyclopedic overview

6 sections

Contents

Medical uses
Pharmacological activity
Society and culture
Legal status
References
Further reading

{{Chembox | Watchedfields = changed | verifiedrevid = 434307328 | ImageFile = Aplidine.svg | ImageSize = 200 | SystematicName = (2S)-N-[(1R)-1-({(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-10-[(2S)-Butan-2-yl]-11-hydroxy-3-[(4-methoxyphenyl)methyl]-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,8,13,16,18,21-heptaoxo-15-(propan-2-yl)docosahydro-15H-pyrrolo[2,1-d][10,19,1,4,7,14]dioxatetraazacyclotricosin-7-yl}carbamoyl)-3-methylbutyl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide | OtherNames = Aplidine; Aplidin, dehydrodidemnin B; Aplidin; N-[1-(1,2-Dioxopropyl)-L-prolyl]didemnin A |Section1= |Section2= | Section6 = | Section7 = }}

Plitidepsin, also known as dehydrodidemnin B and sold under the brand name Aplidin, is a chemical compound extracted from the ascidian Aplidium albicans.

Excerpted from Wikipedia’s “aplidin” article, available under the CC BY-SA 4.0 licence.

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