U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H31NO5S
Molecular Weight 421.55
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LATRUNCULIN A

SMILES

[H][C@]1(CSC(=O)N1)[C@@]2(O)C[C@@]3([H])C[C@@H](CC[C@H](C)C=C\C=C\CCC(C)=CC(=O)O3)O2

InChI

InChIKey=DDVBPZROPPMBLW-IZGXTMSKSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H31NO5S
Molecular Weight 421.55
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Latrunculin A is a naturally occurring toxin that can be purified from the red sea sponge Latrunculia magnifica. It disrupts actin polymerization and prevents mitotic spindle formation; therefore preventing proper cellular replication. It was discovered that latrunculin A has strong anticancer effects, and it was investigated as a treatment candidate for peritoneal dissemination of gastric cancer.

CNS Activity

Originator

Sources: DOI: 10.1016/0040-4039(80)80255-3
Curator's Comment: Latrunculins isolation. DOI: 10.1007/BF00390634

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P68133
Gene ID: 58.0
Gene Symbol: ACTA1
Target Organism: Homo sapiens (Human)
0.2 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A mutation of beta -actin that alters depolymerization dynamics is associated with autosomal dominant developmental malformations, deafness, and dystonia.
2006 Jun
Myosin light chain kinase plays a role in the regulation of epithelial cell survival.
2006 Jun 1
Azaspiracid-1 inhibits endocytosis of plasma membrane proteins in epithelial cells.
2010 Sep
Patents

Sample Use Guides

in mice: Mice bearing peritoneally disseminated MKN45 or NUGC-4 (gastric cancer cells) tumors were prepared by an i.p. inoculation of 1×107 cells in 5% DMSO/0.7 mL PBS. On day 3, 10 and 17 after tumor inoculation, each mouse was given an i.p.injection of latrunculin A. The i.p. injection group were treated with latrunculin A (0.05 mg/kg, 5% DMSO in 0.7 mL PBS, n=14, MKN45; and n=10, NUGC-4), and the control group was treated with 5% DMSO in 0.7 mL PBS (n=19, MKN45; and n=9, NUGC-4). Negative (n=10) group was given latrunculin A without tumor inoculation.
Route of Administration: Intraperitoneal
It was reported that 25 µM Latrunculin A (LatA) blocked actin polymerization in the capacitated sperm head, resulting in a marked decrease in sperm with relocated IZUMO1 during the A23187-induced acrosome reaction and cumulus layer penetration. Treated sperm also exhibited reduced zona pellucida penetration and fertilizing capacity. Interestingly, LatA-treated sperm present in the perivitelline space of eggs did not show impaired IZUMO1 relocation.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:45:14 UTC 2023
Edited
by admin
on Fri Dec 15 17:45:14 UTC 2023
Record UNII
SRQ9WWM084
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LATRUNCULIN A
MI  
Common Name English
LATRUNCULIN A [MI]
Common Name English
2-THIAZOLIDINONE, 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)-, (4R)-
Systematic Name English
NSC-613011
Code English
LAT-A
Brand Name English
LATRUNCULIN
Common Name English
2-THIAZOLIDINONE, 4-(17-HYDROXY-5,12-DIMETHYL-3-OXO-2,16-DIOXABICYCLO(13.3.1)NONADECA-4,8,10-TRIEN-17-YL)-, (1R-(1R*,4Z,8E,10Z,12S*,15R*,17R*(R*)))-
Common Name English
Code System Code Type Description
WIKIPEDIA
Latrunculin
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY
DRUG BANK
DB02621
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY
MESH
C037067
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID90893488
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY
CAS
76343-93-6
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY
CHEBI
69136
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY
MERCK INDEX
m6703
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY Merck Index
NSC
613011
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY
PUBCHEM
445420
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY
FDA UNII
SRQ9WWM084
Created by admin on Fri Dec 15 17:45:14 UTC 2023 , Edited by admin on Fri Dec 15 17:45:14 UTC 2023
PRIMARY