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targets (3)
for drugs
Identification
Name Latrunculin A
Accession Number DB02621 (EXPT02004)
Type small molecule
Groups experimental
Description

Latrunculin A is an actin binding macrolide purified from the red sea sponge Latrunculia magnifica. It is under investigation for the treatment of cancer. It disrupts actin polymerization, prevents mitotic spindle formation and thus cell replication.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
4-(17-Hydroxy-5,12-Dimethyl-3-Oxo-2,16-Dioxabicyclo[13.3.1]Nonadeca-4,8,10-Trien-17-Yl)-2-Thiazolidinone
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories Not Available
CAS number Not Available
Weight Average: 421.55
Monoisotopic: 421.192293797
Chemical Formula C22H31NO5S
InChI Key InChIKey=DDVBPZROPPMBLW-ZJBINBEQSA-N
InChI
InChI=1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/b4-3-,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1
Plain Text
IUPAC Name
(4R)-4-[(1R,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one
SMILES
[H][C@]1(CSC(=O)N1)[C@@]1(O)C[C@@]2([H])C[C@@]([H])(CC[C@]([H])(C)\C=C/C=C\CC\C(C)=C/C(=O)O2)O1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
Pharmacodynamics Not Available
Mechanism of action Not Available
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 2.04e-02 g/l ALOGPS
logP 3 ALOGPS
logP 4.31 ChemAxon
logS -4.3 ALOGPS
pKa (strongest acidic) 11.36 ChemAxon
pKa (strongest basic) -4.4 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 84.86 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 115.96 ChemAxon
polarizability 44.78 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Coue M, Brenner SL, Spector I, Korn ED: Inhibition of actin polymerization by latrunculin A. FEBS Lett. 1987 Mar 23;213(2):316-8. Pubmed
  2. Konishi H, Kikuchi S, Ochiai T, Ikoma H, Kubota T, Ichikawa D, Fujiwara H, Okamoto K, Sakakura C, Sonoyama T, Kokuba Y, Sasaki H, Matsui T, Otsuji E: Latrunculin a has a strong anticancer effect in a peritoneal dissemination model of human gastric cancer in mice. Anticancer Res. 2009 Jun;29(6):2091-7. Pubmed
  3. Foissner I, Wasteneys GO: Wide-ranging effects of eight cytochalasins and latrunculin A and B on intracellular motility and actin filament reorganization in characean internodal cells. Plant Cell Physiol. 2007 Apr;48(4):585-97. Epub 2007 Feb 27. Pubmed 17327257
External Links
Resource Link
PubChem Compound 46936439 Link_out
PubChem Substance 46508901 Link_out
BindingDB 50235955 Link_out
HET LAR Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Actin, alpha skeletal muscle

Pharmacological action: unknown
Actions: inhibitor

Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells

Organism class: human
UniProt ID: P68133 Link_out
Gene: ACTA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Coue M, Brenner SL, Spector I, Korn ED: Inhibition of actin polymerization by latrunculin A. FEBS Lett. 1987 Mar 23;213(2):316-8. Pubmed 3556584
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Gelsolin

Pharmacological action: unknown

Calcium-regulated, actin-modulating protein that binds to the plus (or barbed) ends of actin monomers or filaments, preventing monomer exchange (end-blocking or capping). It can promote the assembly of monomers into filaments (nucleation) as well as sever filaments already formed

Organism class: human
UniProt ID: P06396 Link_out
Gene: GSN Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Iota toxin component Ia

Pharmacological action: unknown
Organism class: bacterial
UniProt ID: Q46220 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA

References:
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:21