γ-Linolenoyl-CoA

Names

[ Name ]:
γ-Linolenoyl-CoA

[Synonym ]:
γ-Linolenoyl-CoA
Cyclopiazonic acid from Penicillium cyclopium
Adenosine, 5'-O-[hydroxy[[hydroxy[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[[2-[[(6Z,9Z,12Z)-1-oxo-6,9,12-octadecatrien-1-yl]thio]ethyl]amino]propyl]amino]butoxy]phosphinyl]oxy]phosphinyl]-, 3'-(dihydrogen phosphate)
9-Phenanthrol
CYCLOPIAZONICACID,BIOTECHGRADE
CPA
PENICILLIUM CYCLOPIUM
S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3λ,5λ- diphosphaheptadecan-17-yl} (6Z,9Z,12Z)-6,9,12-octadecatrienethioate
Cyclopiazonic acid,(6aR,11aS,11bR)-rel-10-Acetyl-2,6,6a,7,11a,11b-hexahydro-7,7-dimethyl-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
MFCD00167445
Cyclopiazonsaeure

Biological Activity

[Description]:

Cyclopiazonic acid (CPA), a neurotoxic secondary metabolite (SM) made by A. flavus, is a nanomolar inhibitor of endoplasmic reticulum calcium ATPase (Ca2+ATPase; SERCA) and a potent inducer of cell death in plants[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Others

[References]

[1]. Chalivendra SC, et al. Cyclopiazonic Acid Is a Pathogenicity Factor for Aspergillus flavus and a Promising Target for Screening Germplasm for Ear Rot Resistance. Mol Plant Microbe Interact. 2017 May;30(5):361-373.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
598.6ºC at 760mmHg

[ Melting Point ]:
245-246ºC

[ Molecular Formula ]:
C₂₀H₂₀N₂O₃

[ Molecular Weight ]:
1027.948

[ Flash Point ]:
315.8ºC

[ Exact Mass ]:
1027.329224

[ PSA ]:
73.40000

[ LogP ]:
2.96

[ Index of Refraction ]:
1.626

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY8587000

CAS REGISTRY NUMBER :: 18172-33-3

LAST UPDATED :: 199412

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C20-H20-N2-O3

MOLECULAR WEIGHT :: 336.42

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 36 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Liver - hepatitis (hepatocellular necrosis), diffuse Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Gastrointestinal - changes in structure or function of endocrine pancreas Liver - hepatitis (hepatocellular necrosis), diffuse Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 64 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 13 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 364 mg/kg/13W-I

TOXIC EFFECTS :: Liver - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 32 mg/kg/4D-I

TOXIC EFFECTS :: Liver - other changes Blood - changes in leukocyte (WBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - sex ratio

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 240 mg/kg

SEX/DURATION :: male 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 20 mg/kg

SEX/DURATION :: female 12-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 mg/kg

SEX/DURATION :: female 5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 30 mg/kg

SEX/DURATION :: female 6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - oogenesis Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 15 mg/kg

SEX/DURATION :: female 5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 1 umol/plate

REFERENCE :: AEMIDF Applied and Environmental Microbiology. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.31- 1976- Volume(issue)/page/year: 47,1355,1984

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S45;S36/S37/S39

[ RIDADR ]:
UN 2811 6.1/PG 2

[ RTECS ]:
UY8587000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Articles

Acid-sensing ion channel 3 decreases phosphorylation of extracellular signal-regulated kinases and induces synoviocyte cell death by increasing intracellular calcium.

Arthritis. Res. Ther. 16(3) , R121, (2014)

Acid-sensing ion channel 3 (ASIC3) is expressed in synoviocytes, activated by decreases in pH, and reduces inflammation in animal models of inflammatory arthritis. The purpose of the current study was...

Store-operated calcium entry compensates fast ER calcium loss in resting hippocampal neurons.

Cell Calcium 58 , 147-59, (2015)

The endoplasmic reticulum (ER) acts as a dynamic calcium store and is involved in the generation of specific patterns of calcium signals in neurons. Calcium is mobilized from the ER store by multiple ...

Mechanisms of the sarcoplasmic reticulum Ca2+ release induced by P2X receptor activation in mesenteric artery myocytes.

Pharmacol. Rep. 66(3) , 363-72, (2014)

ATP is one of the principal sympathetic neurotransmitters which contracts vascular smooth muscle cells (SMCs) via activation of ionotropic P2X receptors (P2XRs). We have recently demonstrated that con...

Related Compounds

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