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M6418

Sigma-Aldrich

Manumycin A from Streptomyces parvulus

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About This Item

Empirical Formula (Hill Notation):
C31H38N2O7
CAS Number:
52665-74-4
Molecular Weight:
550.64
MDL number:
MFCD00920782
UNSPSC Code:
12352200
PubChem Substance ID:
24897011
NACRES:
NA.32

Assay

≥97% (HPLC)

Quality Level

200

form

powder

solubility

methanol: 9.80-10.20 mg/mL, clear, yellow to very deep yellow

storage temp.

2-8°C

SMILES string

CCCC[C@@H](C)\C=C(C)\C=C(/C)C(=O)NC1=C[C@@](O)(\C=C\C=C\C=C\C(=O)NC2=C(O)CCC2=O)[C@@H]3O[C@H]3C1=O

InChI

1S/C31H38N2O7/c1-5-6-11-19(2)16-20(3)17-21(4)30(38)32-22-18-31(39,29-28(40-29)27(22)37)15-10-8-7-9-12-25(36)33-26-23(34)13-14-24(26)35/h7-10,12,15-19,28-29,34,39H,5-6,11,13-14H2,1-4H3,(H,32,38)(H,33,36)/b8-7+,12-9+,15-10+,20-16+,21-17+/t19-,28?,29-,31+/m1/s1

InChI key

TWWQHCKLTXDWBD-YCWSEAROSA-N

Application

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.

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.
Potent inhibitor of Ras farnesyltransferase.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Hara et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(6), 2281-2285 (1993-03-15)
A microbial screen using a yeast strain with conditional deficiency in the GPA1 gene was carried out to search for inhibitors of protein farnesyltransferase (PFT). A strain of Streptomyces was found to produce active compounds named UCF1-A, UCF1-B, and UCF1-C.
Binding of manumycin A inhibits IkappaB kinase beta activity
Bernier M, et al.
Test, 281(5), 2551-2561 (2006)
Daniel Z Bar et al.
Nucleus (Austin, Tex.), 1(6), 499-505 (2011-02-18)
Fibroblasts derived from Hutchinson-Gilford progeria syndrome (HGPS) patients and dermal cells derived from healthy old humans in culture display age-dependent progressive changes in nuclear architecture due to accumulation of farnesylated lamin A. Treating human HGPS cells or mice expressing farnesylated
Vivek Sharma et al.
Inflammation, 35(2), 516-519 (2011-05-11)
We have recently reported that Ras acts as an intermediate coactivator in IL-1β-mediated hypoxia-inducible factor-1α (HIF-1α) activation in glioblastoma multiforme (GBM). Since HIF-1α plays a crucial role in linking inflammatory and oncogenic pathways, we investigated whether this IL1β-Ras-HIF-1α signaling axis
Pengfei Xie et al.
Applied microbiology and biotechnology, 96(2), 451-460 (2012-05-05)
Asukamycin, a member of the manumycin family of antibiotics, exhibits strong antibacterial, antifungal, and antineoplastic activities. However, its production in the wild-type strain of Streptomyces nodosus subsp. asukaensis ATCC 29757 is relatively low. Recently, the biosynthetic gene cluster for asukamycin
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