Latrunculin B, actin polymerization inhibitor

Key facts

CAS number

76343-94-7

Purity

>96%

Form

Solid

form

Source

Latrunculia magnifica

Molecular weight

395.5 Da

Molecular formula

C₂₀H₂₉NO₅S

PubChem

6436219

Nature

Native

Solubility

Soluble in DMSO (25 mg/ml)

Soluble in ethanol (25 mg/ml)

Biochemical name

latrunculin B

Biological description

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, (ab144290) (IC₅₀ values are 7.1 and 4.8 μM for HCT116 and MDA-MB-435 cells respectively). Shows antiglaucoma effects in vivo.

Canonical 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

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

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