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MANUMYCIN A

CAS No.
52665-74-4
Chemical Name:
MANUMYCIN A
Synonyms
UCF 1C;manumycin;NSC 622141;MANUMYCIN A;Chiromycin A;MANUMYCIN A, STREPTOMYCES PARVULUS;manumycin A from streptomyces parvulus;Manumycin A, Streptomyces parvulus - CAS 52665-74-4 - Calbiochem;N-[5-Hydroxy-5-[7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide;(2E,4E)-N-[(5R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide
CBNumber:
CB1103133
Molecular Formula:
C31H38N2O7
Molecular Weight:
550.64
MDL Number:
MFCD18432704
MOL File:
52665-74-4.mol
MSDS File:
SDS
Last updated:2023-06-08 09:03:08

MANUMYCIN A Properties

Boiling point 863.6±65.0 °C(Predicted)
Density 1.26±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in DMSO (up to 10 mg/ml), in Ethanol (up to 5 mg/ml) or in DMF (up to 20 mg/ml)
pka 3.80±0.30(Predicted)
form Yellow to brown solid
color Yellow
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO, ethanol, or DMF may be stored at -20°C for up to 3 months.
FDA UNII OIQ298X4XD

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302+H312-H319
Precautionary statements  P264-P270-P280-P301+P312-P302+P352-P305+P351+P338-P321-P330-P362+P364-P337+P313-P501
WGK Germany  3
HS Code  2941900000
NFPA 704
0
2 0

MANUMYCIN A price More Price(17)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich M6418 Manumycin A from Streptomyces parvulus 52665-74-4 5mg $781 2024-03-01 Buy
Cayman Chemical 10010497 Manumycin A ≥98% 52665-74-4 1mg $111 2024-03-01 Buy
Cayman Chemical 10010497 Manumycin A ≥98% 52665-74-4 5mg $412 2024-03-01 Buy
TRC M186000 Manumycin A, 52665-74-4 0.5mg $225 2021-12-16 Buy
Usbiological 207273 Manumycin A 52665-74-4 1mg $325 2021-12-16 Buy
Product number Packaging Price Buy
M6418 5mg $781 Buy
10010497 1mg $111 Buy
10010497 5mg $412 Buy
M186000 0.5mg $225 Buy
207273 1mg $325 Buy

MANUMYCIN A Chemical Properties,Uses,Production

Description

Manumycin A is an antibiotic that acts as a potent and selective farnesyltransferase (FTase) inhibitor with anti-tumor activity. It inhibits rat brain FTase with a Ki value of 1.2 μM, thereby preventing Ras activation which requires farnesylation at the C-terminus for membrane attachment. It exhibits significant antitumor activity against Ki-ras-activated solid tumors in mice at a dose of 6.3 mg/kg. Manymycin A inhibits IκB kinase (IKK), independent of FTase inhibition, in an number of cells types with effective concentrations of 2-10 μM. In ApoE-deficient mice, Manumycin A treatment for 22 weeks at 5 mg/kg reduced aortic fatty streak lesion size to 43% of vehicle-treated animals, indicating FTase inhibition as a potential target for prevention or treatment of atherosclerosis.

Uses

Manumycin A is an antibiotic that acts as a potent and selective farnesyltransferase (FTase) inhibitor with anti-tumor activity.

Uses

Manumycin A from Streptomyces parvulus has been used to inhibit IκB kinase (IKK)b?nuclear κ-B essential modulator (NEMO) interaction in the homogeneous time-resolved fluorescence (HTRF)-based binding assay.

Definition

ChEBI: Manumycin A is a polyketide with formula C31H38N2O7 initially isolated from Streptomyces parvulus as a result of a random screening program for farnesyl transferase (FTase) inhibitors. It is a natural product that exhibits anticancer and antibiotic properties. It has a role as an EC 1.8.1.9 (thioredoxin reductase) inhibitor, an EC 2.5.1.58 (protein farnesyltransferase) inhibitor, an antineoplastic agent, an apoptosis inducer, an antimicrobial agent, a bacterial metabolite, an antiatherosclerotic agent and a marine metabolite. It is a polyketide, an enamide, an epoxide, an organic heterobicyclic compound, a secondary carboxamide and a tertiary alcohol.

Biochem/physiol Actions

Manumycin A is a natural monomeric epoxyquinoid. It has an ability to inhibit tumor necrosis factor (TNF) induced IκB kinase (IKK) activity in various cell types. In addition, manumycin A exhibits anti-tumor property by inhibiting farnesylation of oncogenic Ras.

References

1) Hara?et al.?(1993),?Identification of Ras Farnesyltransferase inhibitors by microbial screening; Proc. Natl. Acad. Sci. USA,?90?2281 2) DiPaolo?et al.?(2000),?Manumycin inhibits ras signal transduction pathway and induces apoptosis in COLO320-DM human colon tumour cells; Br. J. Cancer,?82?905 3) Arenz?et al.?(2001),?Manumycin A and its analogies are irreversible inhibitors of neutral sphingomyelinase; Chem. Bio. Chem.,?2?141 4) Sharma?et al.?(2012),?Farnesyltransferase inhibitor manumycin targets IL1β-Ras-HIF-1α axis in tumor cells of diverse origin; Inflammation,?35?516 5) Saha and Nandi (2009),?Farnesyltransferase inhibitors reduce Ras activation and ameliorate acetaminophen-induced liver injury in mice; Hepatology,?50?1547 6) Singha?et al.?(2013),?Manumycin A inhibits triple-negative breast cancer growth through LC3-mediated cytoplasmic vacuolation death; Cell Death Dis.,?4?e457

MANUMYCIN A Preparation Products And Raw materials

Raw materials

Preparation Products

MANUMYCIN A Suppliers

Global( 90)Suppliers
Supplier Tel Email Country ProdList Advantage
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58
BOC Sciences
+16314854226 inquiry@bocsci.com United States 19743 58
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
+86-19164747840 +86-13119157289 13119157289@163.com China 2971 58
Aladdin Scientific
+1-833-552-7181 sales@aladdinsci.com United States 52927 58
J & K SCIENTIFIC LTD. 010-82848833 400-666-7788 jkinfo@jkchemical.com China 96815 76
Dalian Meilun Biotech Co., Ltd. 0411-62910999 13889544652 sales@meilune.com China 4647 58
Shanghai Tauto Biotech Co., Ltd. 021-51320588 tauto@tautobiotech.com China 3989 66
Guangzhou Isun Pharmaceutical Co., Ltd 020-39119399 18927568969 isunpharm@qq.com China 4428 55
Sigma-Aldrich 021-61415566 800-8193336 orderCN@merckgroup.com China 51471 80
Shanghai EFE Biological Technology Co., Ltd. 021-65675885 18964387627 info@efebio.com China 9709 58
MANUMYCIN A MANUMYCIN A, STREPTOMYCES PARVULUS N-[5-Hydroxy-5-[7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide manumycin manumycin A from streptomyces parvulus NSC 622141 UCF 1C (2E,4E)-N-[(5R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide Manumycin A, Streptomyces parvulus - CAS 52665-74-4 - Calbiochem 2,4-Decadienamide, N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyl-, (2E,4E,6R)- Chiromycin A 52665-74-4 Cell Signaling and Neuroscience Cell Biology BioChemical Post-translational Modification G Proteins and Cyclic Nucleotides G Protein Function Farnesyl transferase, RasG Proteins and Cyclic Nucleotides D to Enzyme Inhibitors by Enzyme G Protein Function Post-translational Modification