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Latrunculin A

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Identification

Generic Name
Latrunculin A
DrugBank Accession Number
DB02621
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 421.55
Monoisotopic: 421.192293797
Chemical Formula
C22H31NO5S
Synonyms
  • (+)-latrunculin A
  • (4R)-4-[(1R,4Z,8E,10Z,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
  • LAT-A
  • LatA
External IDs
  • NSC-613011
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UActin, alpha skeletal muscle
inhibitor
Humans
UGelsolinNot AvailableHumans
UIota toxin component IaNot AvailableClostridium perfringens
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolides and analogues
Sub Class
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
show 5 more
Substituents
Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Azacycle / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Enoate ester / Hemiacetal / Hydrocarbon derivative
show 14 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cyclic hemiketal, macrolide, oxabicycloalkane, thiazolidinone (CHEBI:69136)
Affected organisms
Not Available

Chemical Identifiers

UNII
SRQ9WWM084
CAS number
76343-93-6
InChI Key
DDVBPZROPPMBLW-IZGXTMSKSA-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
IUPAC Name
(4R)-4-[(1R,4Z,8E,10Z,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@H]2C[C@@H](CC[C@H](C)\C=C/C=C/CC\C(C)=C/C(=O)O2)O1

References

General 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. [Article]
  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. [Article]
  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. [Article]
PubChem Compound
6437378
PubChem Substance
46508901
ChemSpider
393069
BindingDB
65515
ChEBI
69136
ChEMBL
CHEMBL404116
ZINC
ZINC000005766575
PDBe Ligand
LAR
Wikipedia
Latrunculin
PDB Entries
1esv / 1ijj / 1lcu / 1rdw / 1rfq / 1sqk / 2a5x / 2q1n / 2q31 / 3buz …
show 8 more

Clinical Trials

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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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4Not Yet RecruitingTreatmentAllografts1somestatusstop reasonjust information to hide

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
PropertyValueSource
Water Solubility0.0204 mg/mLALOGPS
logP3ALOGPS
logP4.31Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)11.36Chemaxon
pKa (Strongest Basic)-4.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area84.86 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity115.96 m3·mol-1Chemaxon
Polarizability44.76 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8669
Blood Brain Barrier-0.7361
Caco-2 permeable-0.648
P-glycoprotein substrateSubstrate0.7253
P-glycoprotein inhibitor INon-inhibitor0.9156
P-glycoprotein inhibitor IINon-inhibitor0.9955
Renal organic cation transporterNon-inhibitor0.9178
CYP450 2C9 substrateNon-substrate0.8784
CYP450 2D6 substrateNon-substrate0.7988
CYP450 3A4 substrateSubstrate0.5818
CYP450 1A2 substrateNon-inhibitor0.7734
CYP450 2C9 inhibitorNon-inhibitor0.8112
CYP450 2D6 inhibitorNon-inhibitor0.9139
CYP450 2C19 inhibitorNon-inhibitor0.7337
CYP450 3A4 inhibitorNon-inhibitor0.9704
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9312
Ames testNon AMES toxic0.7094
CarcinogenicityNon-carcinogens0.9597
BiodegradationNot ready biodegradable0.5156
Rat acute toxicity2.6858 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9838
hERG inhibition (predictor II)Non-inhibitor0.9342
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0zfr-2691200000-5684db2c5c501e83868d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0002900000-0e5c2b2ee8f9461b8d5d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0005900000-aad17893f606c1f72a60
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0109800000-083429841a54876e374e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0089-9114400000-ffc3c421ca047117a450
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0095000000-8d2f9076fa497d4cb342
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003u-9236100000-b1839ebcb7626dd2a6a0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-208.0826789
predicted
DarkChem Lite v0.1.0
[M-H]-210.64896
predicted
DeepCCS 1.0 (2019)
[M+H]+208.2966789
predicted
DarkChem Lite v0.1.0
[M+H]+212.54436
predicted
DeepCCS 1.0 (2019)
[M+Na]+208.6526789
predicted
DarkChem Lite v0.1.0
[M+Na]+218.32231
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Actin, alpha skeletal muscle
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells
Specific Function
ADP binding
Gene Name
ACTA1
Uniprot ID
P68133
Uniprot Name
Actin, alpha skeletal muscle
Molecular Weight
42050.67 Da
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. [Article]
  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. [Article]
Details2. Gelsolin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
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 (PubMed:19666512). Plays a role in ciliogenesis (PubMed:20393563)
Specific Function
actin binding
Gene Name
GSN
Uniprot ID
P06396
Uniprot Name
Gelsolin
Molecular Weight
85696.935 Da
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. [Article]
Details3. Iota toxin component Ia
Kind
Protein
Organism
Clostridium perfringens
Pharmacological action
Unknown
General Function
Not Available
Specific Function
nucleotide binding
Gene Name
Not Available
Uniprot ID
Q46220
Uniprot Name
Iota toxin component Ia
Molecular Weight
52316.715 Da
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:44