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18172-33-3

18172-33-3 structure
18172-33-3 structure
  • Name: γ-Linolenoyl-CoA
  • Chemical Name: (6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
  • CAS Number: 18172-33-3
  • Molecular Formula: C20H20N2O3
  • Molecular Weight: 1027.948
  • Catalog: Signaling Pathways Membrane Transporter/Ion Channel Calcium Channel
  • Create Date: 2018-09-22 22:49:20
  • Modify Date: 2024-01-03 16:27:30
  • 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].
Name (6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
Synonyms 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
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
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.
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

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
Symbol GHS06
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)
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