Microcystin-LR

Modify Date: 2025-08-20 22:08:12

Microcystin-LR Structure
Microcystin-LR structure
Common Name Microcystin-LR
CAS Number 101043-37-2 Molecular Weight 995.172
Density 1.3±0.1 g/cm3 Boiling Point N/A
Molecular Formula C49H74N10O12 Melting Point N/A
MSDS USA Flash Point 11 °C
Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger

 Use of Microcystin-LR


Microcystin-LR is a potent inhibitor of type 1 and type 2A protein phosphatases (PP1 and PP2A), with IC50s of 1.7 nM and 0.04 nM, respectively. Sequence: Ala-D-Ala-Leu-D-{Bas}-Arg-{Oaa}-D-{Ggu}.

 Names

Name microcystin-LR
Synonym More Synonyms

 Microcystin-LR Biological Activity

Description Microcystin-LR is a potent inhibitor of type 1 and type 2A protein phosphatases (PP1 and PP2A), with IC50s of 1.7 nM and 0.04 nM, respectively. Sequence: Ala-D-Ala-Leu-D-{Bas}-Arg-{Oaa}-D-{Ggu}.
Related Catalog
Target

IC50: 1.7 nM (PP1), 0.04 nM (PP2A)[1].

In Vitro Microcystins are toxic molecules produced by cyanobacterial blooms due to water eutrophication[2]. Microcystin-LR proves to be a potent inhibitor of type 1 (IC50=1.7 nM) and type 2A (IC50= 0.04 nM) protein phosphatases. Microcystin-LR inhibits the activity of both type 1 and type 2A phosphatases >10-fold more potently than okadaic acid under the same conditions. Type 2A protein phosphatases in dilute mammalian cell extracts are found to be completely inhibited by 0.5 nM microcystin-LR while type 1 protein phosphatases are only slightly affected at this concentration[1].
References

[1]. Honkanen RE, et al. Characterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phosphatases. J Biol Chem. 1990 Nov 15;265(32):19401-4.

[2]. Lone Y, et al. Microcystin-LR Induced Immunotoxicity in Mammals. J Toxicol. 2016:8048125.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Molecular Formula C49H74N10O12
Molecular Weight 995.172
Flash Point 11 °C
Exact Mass 994.548767
PSA 340.64000
LogP -1.54
Appearance of Characters solid film
Index of Refraction 1.598
InChIKey ZYZCGGRZINLQBL-GWRQVWKTSA-N
SMILES C=C1C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(C(=O)O)C(C)C(=O)NC(CCCN=C(N)N)C(=O)NC(C=CC(C)=CC(C)C(Cc2ccccc2)OC)C(C)C(=O)NC(C(=O)O)CCC(=O)N1C
Water Solubility ethanol: 1 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GT2810000
CHEMICAL NAME :
Cyanoginosin LA, 5-L-arginine-
CAS REGISTRY NUMBER :
101043-37-2
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C49-H74-N10-O12
MOLECULAR WEIGHT :
995.33

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 26,603,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 ug/kg
TOXIC EFFECTS :
Cardiac - other changes Liver - hepatitis (hepatocellular necrosis), zonal Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 8,221,1988
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
18 mg/m3/10M
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 28,605,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
32500 ng/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Kidney, Ureter, Bladder - other changes Skin and Appendages - hair
REFERENCE :
JEPOEC Journal of Environmental Pathology, Toxicology and Oncology. (Chem-Orbital, POB 134, Park Forest, IL 60466) V.5(4)- 1984- Volume(issue)/page/year: 9(3),221,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
60 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) Skin and Appendages - hair
REFERENCE :
SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 220,1383,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CBINA8 Chemico-Biological Interactions. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1969- Volume(issue)/page/year: 63,215,1987 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2205 ug/kg/6W-I
TOXIC EFFECTS :
Liver - other changes Liver - changes in liver weight Related to Chronic Data - death
REFERENCE :
AJBSAM Australian Journal of Biological Sciences. (Commonwealth Scientific and Industrial Research Organization, 314 Albert St., E. Melbourne, Vic. 3002, Australia) V.6- 1953- Volume(issue)/page/year: 31,209,1978

 Safety Information

Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger
Hazard Statements H225-H301-H311-H331-H370
Precautionary Statements P210-P260-P280-P301 + P310-P311
Personal Protective Equipment Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US)
Hazard Codes T+
Risk Phrases 26/27/28-36/37/38-43
Safety Phrases S26;S45;S36/S37/S39
RIDADR UN 2811 6.1/PG 1
WGK Germany 3
RTECS GT2810000
Hazard Class 6.1

 Synthetic Route

~%

Microcystin-LR Structure

Microcystin-LR

CAS#:101043-37-2

Literature: Chemical Research in Toxicology, , vol. 11, # 3 p. 159 - 163

 Articles45

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 Synonyms

akerstox
TOXIN,BLUE-GREENALGA
EINECS 200-659-6
Microcystin-LR
microcystin-lr solution
1,4,7,10,14,17,21-Heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid, 15-[3-[(aminoiminomethyl)amino]propyl]-3,6,9,13,16,20-hexahydroxy-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-1,3-heptadien-1-yl]-1,5,12,19-tetramethyl-2-methylene-8-(2-methylpropyl)-25-oxo-, (3E,5R,6E,8S,9E,11R,12S,13E,15S,16E,18S,19S,20E,22R)-
toxin-lr
microcystin LR
MFCD00131607
1,4,7,10,14,17,21-Heptaazacyclopentacosane-11,22-dicarboxylic acid, 15-[3-[(aminoiminomethyl)amino]propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-1,3-heptadien-1-yl]-1,5,12,19-tetramethyl-2-methylene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-, (5R,8S,11R,12S,15S,18S,19S,22R)-
5-L-Arginine-cyanoginosin
(3E,5R,6E,8S,9E,11R,12S,13E,15S,16E,18S,19S,20E,22R)-15-(3-Carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-8-isobutyl-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-1,3-heptadien-1-yl]-1,5,12,19-tetramethyl-2-methylene-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid
5-L-Arginine-microcystin LA
microcystin-a
MCYST-LR
(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-Carbamimidamidopropyl)-8-isobutyl-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-1,3-heptadien-1-yl]-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid
CYANOGINOSIN-LR
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