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viridicatumtoxin

CAS No.
39277-41-3
Chemical Name:
viridicatumtoxin
Synonyms
NSC 159628;viridicatumtoxin;Spiro[2-cyclohexene-1,2'(1'H)-cyclopenta[de]naphthacene]-9'-carboxamide, 7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-, (1R,7'aR,11'aR,12'R)-rel-(-)-
CBNumber:
CB91382922
Molecular Formula:
C30H31NO10
Molecular Weight:
565.57
MDL Number:
MFCD01675248
MOL File:
39277-41-3.mol
MSDS File:
SDS
Last updated:2023-06-08 09:03:09

viridicatumtoxin Properties

Melting point 235°C (rough estimate)
Boiling point 630.75°C (rough estimate)
Density 1.3203 (rough estimate)
refractive index 1.6310 (estimate)
storage temp. Store at -20°C
solubility DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
form A solid
EWG's Food Scores 1
FDA UNII S8N62PLU21

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P321-P330-P405-P501
NFPA 704
0
2 0

viridicatumtoxin price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 25480 Viridicatumtoxin ≥98% 39277-41-3 1mg $227 2024-03-01 Buy
Cayman Chemical 25480 Viridicatumtoxin ≥98% 39277-41-3 5mg $954 2024-03-01 Buy
TRC V673905 Viridicatumtoxin 39277-41-3 1mg $230 2021-12-16 Buy
American Custom Chemicals Corporation BIO0000728 VIRIDICATUMTOXIN 95.00% 39277-41-3 5MG $504.9 2021-12-16 Buy
AK Scientific 2060DM Viridicatumtoxin 39277-41-3 5mg $1161 2021-12-16 Buy
Product number Packaging Price Buy
25480 1mg $227 Buy
25480 5mg $954 Buy
V673905 1mg $230 Buy
BIO0000728 5MG $504.9 Buy
2060DM 5mg $1161 Buy

viridicatumtoxin Chemical Properties,Uses,Production

Description

Viridicatumtoxin in a mycotoxin originally isolated from Penicillium that has diverse biological activities, including antimicrobial, cytotoxic, and toxic properties. It inhibits the growth of B. subtilis, M. luteus, C. perfringens, B. fragilis, and methicillin-resistant S. aureus (MRSA; MICs = 0.39-1.56 μg/ml), as well as C. albicans, S. cerevisiae, M. racemosus, A. niger, and P. chrysogenum (MICs = 6.2-25 μg/ml), but has no activity against M. smegmatis, E. coli, K. pneumoniae, P. aeruginosa, or S. marcescens (MICs = >100 μg/ml). Viridicatumtoxin inhibits the production of polyprenyl alcohols by S. aureus undecaprenyl pyrophosphate (UPP) synthase, E. coli octaprenyl pyrophosphate synthase (OPS), and S. cerevisiae dehydrodolichyl pyrophosphate (DedoIPP) synthase in vitro (IC50s = 3.1, 21, and 71 μM, respectively). It has cytotoxic effects against human Jurkat T (IC50 = 4.92 μM), chronic lymphocytic leukemia (CLL; LC50 = 0.7-3.5 nM), and bone marrow-derived HS-5 stromal cells. Viridicatumtoxin is toxic to rats and mice when administered intraperitoneally (LD50s = 80 and 90 mg/kg, respectively) and to rats when administered via gastric intubation (LD50 = 122.4 mg/kg), but not to rats or mice when administered orally or through subcutaneous injection.

Uses

Viridicatumtoxin is a tetracycline-like metabolite produced by several species of Penicillium, first isolated in 1976 as a mycotoxin. Initial testing revealed that viridicatumtoxin caused myocardial deterioration, renal tubule necrosis and spleen atrophy. Analogous to the related tetracyclines, viridicatumtoxin was found to be a potent antibacterial, with activity against S. aureus including MRSA and QRSA strains. Little has been published on the mode of action of viridicatumtoxin.

Uses

Viridicatumtoxin is a tetracycline-like metabolite produced by several species of Penicillium.

Definition

ChEBI: A tetracycline-like polyketide antibiotic that is produced by several species of Penicillium and Aspergillus.

viridicatumtoxin Preparation Products And Raw materials

Raw materials

Preparation Products

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viridicatumtoxin NSC 159628 Spiro[2-cyclohexene-1,2'(1'H)-cyclopenta[de]naphthacene]-9'-carboxamide, 7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-, (1R,7'aR,11'aR,12'R)-rel-(-)- 39277-41-3 C30H31NO10