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Latrunculin B - ≥96%, high purity , CAS No.76343-94-7

In stock
Item Number
L275457
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L275457-1mg
1mg
1
$624.90

Cell-permeable actin polymerization inhibitor

Basic Description

Synonyms SY102473 | SCHEMBL2531366 | LAT-B | (+)-latrunculin B | AKOS032947159 | IDI1_002180 | Tektamer | Lat B | (4R)-4-[(1R,4S,5Z,9Z,13R,15R)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]thiazolidin-2-one | 2-THIAZOLIDINONE,
Specifications & Purity Moligand™, ≥96%
Biochemical and Physiological Mechanisms Cell-permeable actin polymerization inhibitor. Forms a 1:1 complex with monomeric G-actin. Shows less potent growth inhibition effects on cancer cell lines than Latrunculin A, (IC 50 values are 7.1 and 4.8 μM for HCT116 and MDA-MB-435 cells r
Storage Temp Protected from light,Store at -20°C,Desiccated
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Grade Moligand™
Note Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description

Latrunculin B, an alkaloid from the Red Sea sponge, is an actin polymerization inhibitor with antifungal and antiprotozoal activity.Latrunculin B modulates the electrophysiological characteristics of the pulmonary veins and attenuates the occurrence of torsade de pointes, and may be used in the study of glaucoma in adolescents.

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Phenylpropanoids and polyketides
Class Macrolides and analogues
Subclass Not available
Intermediate Tree Nodes Not available
Direct Parent Macrolides and analogues
Alternative Parents Oxanes  Thiazolidines  Enoate esters  Thiocarbamic acid derivatives  Organic carbonic acids and derivatives  Lactones  Hemiacetals  Oxacyclic compounds  Monocarboxylic acids and derivatives  Azacyclic compounds  Organopnictogen compounds  Organonitrogen compounds  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular Framework Aliphatic heteropolycyclic compounds
Substituents Macrolide - Oxane - Thiazolidine - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Carboxylic acid ester - Hemiacetal - Lactone - Carbonic acid derivative - Thiocarbamic acid derivative - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Azacycle - Oxacycle - Organic oxide - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Aliphatic heteropolycyclic compound
Description This compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
External Descriptors cyclic hemiketal - macrolide - oxabicycloalkane - thiazolidinone

Associated Targets(Human)

MCF7 (126967 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HCT-116 (91556 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HepG2 (196354 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HUVEC (11049 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDA-MB-435 (38290 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

Aspergillus flavus (8875 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Candida albicans (78123 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A10 (235 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MC-38 (857 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
H4 (48 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name (4R)-4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one
INCHI InChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23)/b5-3-,14-9-/t13-,15-,16-,17+,20-/m1/s1
InChIKey NSHPHXHGRHSMIK-JRIKCGFMSA-N
Smiles CC1CCC2CC(CC(O2)(C3CSC(=O)N3)O)OC(=O)C=C(CCC=C1)C
Isomeric SMILES C[C@H]/1CC[C@@H]2C[C@H](C[C@@](O2)([C@@H]3CSC(=O)N3)O)OC(=O)/C=C(\CC/C=C1)/C
Molecular Weight 395.51
Reaxy-Rn 31789741
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=31789741&ln=

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Find and download the COA for your product by matching the lot number on the packaging.

6 results found

Lot Number Certificate Type Date Item
A2405310 Certificate of Analysis Jun 17, 2025 L275457
F2511675 Certificate of Analysis May 13, 2025 L275457
G2424382 Certificate of Analysis May 09, 2025 L275457
A2405311 Certificate of Analysis Dec 28, 2023 L275457
D23211091 Certificate of Analysis Mar 21, 2023 L275457
D23211185 Certificate of Analysis Mar 21, 2023 L275457

Chemical and Physical Properties

Solubility Soluble in DMSO (25 mg/ml) or ethanol (25 mg/ml)
Sensitivity light sensitive
Molecular Weight 395.500 g/mol
XLogP3 2.900
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 6
Rotatable Bond Count 1
Exact Mass 395.177 Da
Monoisotopic Mass 395.177 Da
Topological Polar Surface Area 110.000 Ų
Heavy Atom Count 27
Formal Charge 0
Complexity 634.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 5
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 2
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 2
Covalently-Bonded Unit Count 1

Citations of This Product

1. Haihong Chen, Yiyi Hu, Guanpin Yang, Pingping Li, Jingru Yin, Xiaoqing Feng, Qiong Wu, Jingyu Zhang, Baoheng Xiao, Zhenghong Sui.  (2023)  Macropinocytosis in Gracilariopsis lemaneiformis (Rhodophyta).  Frontiers in Plant Science,  14  (1225675). 

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