Jasplakinolide
Grundinformationen
- CAS
102396-24-7- Standard-SMILES
C/C1=C\[C@H](C)C[C@H](C)OC(=O)C[C@H](c2ccc(O)cc2)NC(=O)[C@@H](Cc2c(Br)[nH]c3ccccc23)N(C)C(=O)[C@H](C)NC(=O)[C@@H](C)C1- InChIKey
GQWYWHOHRVVHAP-DHKPLNAMSA-N- Summenformel
- C36H45BrN4O6
- Durchschnittliche Molmasse
- 709,7 g/mol
- Monoisotopische Masse
- 708,25225
Überblick
Jaspamide is a cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity. It is an actin polymerization and stabilization inducer. It has a role as an actin polymerisation inducer, an antineoplastic agent, an antifungal agent, a neuroprotective agent, an apoptosis inducer, an animal metabolite and a marine metabolite. It is a member of phenols and a cyclodepsipeptide.
Namen und Bezeichner
- Bevorzugter Name
- Jasplakinolide
- IUPAC
- (4R,7R,10S,13S,15E,17R,19S)-7-[(2-bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone
- Englischer Name
- JASPLAKINOLIDE
- Summenformel
- C36H45BrN4O6
- Molmasse
- 709.67
Namen und Synonyme
jasplakinolideJaspamide102396-24-7(4R,7R,10S,13S,15E,17R,19S)-7-[(2-Bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetroneDTXSID30893487CHEBI:66104NSC 613009beta-Alanine, N-(2-bromo-N-(N-(8-hydroxy-2,4,6-trimethyl-1-oxo-4-nonenyl)-L-alanyl)-N-methyl-D-tryptophyl)-L-3-(4-hydroxyphenyl)-, p-lactone, (2S-(2R*,4E,6S*,8R*))-(4R,7R,10S,13S,15E,17R,19S)-7-((2-bromo-1H-indol-3-yl)methyl)-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetroneRefChem:150384DTXCID801323504(3R,6S,9S,11E,13R,15S,19R)-3-((2-bromo-1H-indol-3-yl)methyl)-19-(4-hydroxyphenyl)-4,6,9,11,13,15-hexamethyl-1,4,7-triazacyclononadec-11-ene-2,5,8,17-tetrone
Weitere Namen anzeigen
JASPLAKINOLIDE, JASPIS JOHNSTONIJasplakinolide, Actin polymerization and stabilization inducerJasplakinolide, Jaspis johnstoni - CAS 102396-24-7 - CalbiochemCyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,6
- Polarare Oberfläche (TPSA)
- 141 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 47
- Formalladung
- 0
- Komplexität
- 1.140
Physikochemische Eigenschaften
- Schmelzpunkt
- 110 ℃ · 110℃ (decomposition)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 2 mg/mL · DMSO: >2mg/mL
- Aggregatzustand
- Off-white solid
- Farbe
- off white to beige
- InChIKey
- GQWYWHOHRVVHAP-DHKPLNAMSA-N
- SMILES
- C[C@H]1C[C@@H](C)\C=C(C)\C[C@H](C)C(=O)N[C@@H](C)C(=O)N(C)[C@H](Cc2c(Br)[nH]c3ccccc23)C(=O)N[C@H](CC(=O)O1)c4ccc(O)cc4
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- ridadr
- 3172
- RTECS-Nr.
- GX7000000
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Anwendungen
BeschreibungJasplakinolide is a natural macrocyclic peptide first isolated from a marine sponge. It potently inhibits the proliferation of PC3 prostate carcinoma cells (IC50 = 35 nM) by binding F-actin (KD = 15 nM). This binding of jasplakinolide to actin, which is competitive with phalloidin, stabilizes actin filaments in vitro but disrupts actin filaments and induces irregular polymerization of monomeric actin in vivo. This compound is used to investigate the role of actin in diverse cellular roles, such as motility, transport, and development.
VerwendenJasplakinolide is a potent inhibitor of prostrate and breast carcinoma cell proliferation. Also acts as an actin stabilizing agent, affecting chromosome movement in studies.
Anbieter35 Anbieter
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
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