3D Mol Similar

JASPLAKINOLIDE

: Iupac Name：(4R,7R,10S,13R,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; CAS No.: 102396-24-7; Molecular Weight：709.682; Modify Date.: 2023-04-13 10:30; Introduction: Jasplakinolide is a potent inhibitor of prostrate and breast carcinoma cell proliferation. Also acts as an actin stabilizing agent, affecting chromosome movement in studies. View more+

Request For Quotation

1. Names and Identifiers

: 1.1 Name; JASPLAKINOLIDE; 1.2 Synonyms; (3S,6R,9R,13S,15R,16E,19S)-3,5,13,15,17,19-Hexamethyl-6-[(2-bromo-1H-indole-3-yl)methyl]-9-(4-hydroxyphenyl)-12-oxa-2,5,8-triazacyclononadeca-16-ene-1,4,7,11-tetraone (4R,7R,10S,13S,15E,17R,19R)-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 (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 [3S,6R,9R,13S,15R,19S,16E,(+)]-6-[(2-Bromo-1H-indol-3-yl)methyl]-9-(4-hydroxyphenyl)-3,5,13,15,17,19-hexamethyl-2,5,8-triaza-12-oxacyclononadecan-16-ene-1,4,7,11-tetrone 1-Oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone, 7-[(2-bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-, (4R,7R,10S,13S,15E,17R,19R)- 1-Oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone, 7-[(2-bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-, (4R,7R,10S,13S,15E,17R,19S)- Cyclo[(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] GQWYWHOHRVVHAP-DHKPLNAMSA-N Jaspamide JASPLAKINOLIDE, JASPIS JOHNSTONI Jasplakinolide, Jaspis johnstoni - CAS 102396-24-7 - Calbiochem jasplakinolide,jaspis johnstoni NSC 613009; View all

1.3 CAS No.: 102396-24-7

1.4 CID: 9831636

1.5 Molecular Formula: C36H45BrN4O6 (isomer)

1.6 Inchi: InChI=1S/C36H45BrN4O6/c1-20-15-21(2)17-23(4)47-32(43)19-30(25-11-13-26(42)14-12-25)40-35(45)31(18-28-27-9-7-8-10-29(27)39-33(28)37)41(6)36(46)24(5)38-34(44)22(3)16-20/h7-15,21-24,30-31,39,42H,16-19H2,1-6H3,(H,38,44)(H,40,45)/b20-15+/t21-,22-,23-,24-,30+,31+/m0/s1

1.7 InChIkey: GQWYWHOHRVVHAP-DHKPLNAMSA-N

1.8 Canonical Smiles: CC1CC(OC(=O)CC(NC(=O)C(N(C(=O)C(NC(=O)C(CC(=C1)C)C)C)C)CC2=C(NC3=CC=CC=C32)Br)C4=CC=C(C=C4)O)C

1.9 Isomers Smiles: C[C@@H]\1C[C@@H](OC(=O)C[C@@H](NC(=O)[C@H](N(C(=O)[C@@H](NC(=O)[C@H](C/C(=C1)/C)C)C)C)CC2=C(NC3=CC=CC=C32)Br)C4=CC=C(C=C4)O)C

2. Properties

2.1 Density: 1.227

2.1 Melting point: 110℃ (decomposition)

2.1 Boiling point: 968.3°Cat760mmHg

2.1 Refractive index: 1.553

2.1 Flash Point: 539.4°C

2.1 Precise Quality: 708.25200

2.1 PSA: 140.83000

2.1 logP: 6.13250

2.1 Solubility: Insuluble (6.5E-3 g/L) (25 oC),

2.2 Appearance: off white to beige

2.3 Color/Form: off white to beige

2.4 Water Solubility: DMSO: >2mg/mL

2.5 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity. JASPLAKINOLIDESupplier

3.2 Usage: Jasplakinolide is a potent inhibitor of prostrate and breast carcinoma cell proliferation. Also acts as an actin stabilizing agent, affecting chromosome movement in studies.

4. Safety and Handling

4.1 Packing Group: III

4.1 Hazard Class: 6.1(b)

4.1 RIDADR: 3172

4.1 WGK Germany: 3

4.1 RTECS: GX7000000

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

View all

6. Other Information

6.0 Uses: Jasplakinolide is a potent inhibitor of prostrate and breast carcinoma cell proliferation. Also acts as an actin stabilizing agent, affecting chromosome movement in studies.

6.1 Definition: ChEBI: A cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity.

6.2 Uses: Jasplakinolide 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.

6.3 体外研究: Jasplakinolide has an IC ₅₀ of 35 nM for the antiproliferative effect of jasplakinolide on PC3 prostate carcinoma cells.
Jasplakinolide (10 μM; for 2 hours) generates binucleated cells when applied during mitosis. Jasplakinolide induces the formation of F-actin-containing apical extensions in Toxoplasma gondii tachyzoites.
Jasplakinolide (1 mM; for 60 min) induces the formation of actin-containing apical extensions in isolated Toxoplasma gondii tachyzoites fixed.

6.4 Uses: Jasplakinolide has been used to analyze its influence on sciatic nerve guidance effect in vivo in chicken embryos. It has also been used to apply on the control cells for the treatment for blocking actin dynamics.

6.5 Biochem/physiol Actions: Jasplakinolide is an actin-specific reagent that promotes actin polymerization and stabilizes actin filaments. In vitro, Jasplakinolidet potently induces actin polymerization by stimulating actin filament nucleation and competes with phalloidin for actin binding (Kd = 15 nM). In vivo, Jasplakinolide has been found to disrupt actin filaments and induce polymerization of monomeric actin into amorphous masses, the exact mechanism of which has not been determined yet. Jasplakinolide differs from other actin stabilizers in that it is cell permeable. This peptide has fungicidal, insecticidal and antiproliferative activity, and is useful for investigating cell processes mediated by actin polymerization and depolymerization, such as cell adhesion, locomotion, endocytosis, and vesicle sorting and release.

7. Computational chemical data

Molecular Weight: 709.682g/mol
Molecular Formula: C₃₆H₄₅BrN₄O₆
Compound Is Canonicalized: True
XLogP3-AA: 5.6
Exact Mass: 708.25225
Monoisotopic Mass: 708.25225
Complexity: 1140
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 141
Heavy Atom Count: 47
Defined Atom Stereocenter Count: 6
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB/uAAAEAAAAAAAAAAAAAAAAWAAAAAwYAAAAAAAAFgB9AAAHgBQCAABPTzhngYyzvPJlgCoAyXyXACCgCAhIiQImaG+bLgIZvrCkbOWcAhm1hHI2heY2eOOoAAAAAACAABAAAAAAAQAAAAAAAAAAA==

8. Recommended Suppliers

Global9SuppliersView all >>

shanghai Tauto Biotech Co., Ltd

Tel:+86-21-51320588 ext. 8025

Jasplakinolide

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2019/11/25

Inquire

VWR International

Tel:800 932 5000

JASPLAKINOLIDE

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2019/11/25

Inquire

EMD Biosciences, Inc.

Tel:858 450 5500

JASPLAKINOLIDE

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2019/11/25

Inquire

Cayman Chemical Company

Tel:+1-(734)-975-3939

Jasplakinolide

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2019/11/25

Inquire

Tocris Bioscience

Tel:+44 (0) 117 916 3333

JASPLAKINOLIDE

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2019/11/25

Inquire

Recently Updated : 1009119-62-3 2446484-57-5 2446481-80-5 1118567-46-6 1447940-07-9 2947584-56-5 32259-88-4 1372158-13-8 2813950-07-9 849481-53-4