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Merck
CN

N2019

Sigma-Aldrich

Nogalamycin

≥95%, from Streptomyces nogalater

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About This Item

Empirical Formula (Hill Notation):
C39H49NO16
CAS Number:
1404-15-5
Molecular Weight:
787.80
MDL number:
MFCD00083442
UNSPSC Code:
51111755
PubChem Substance ID:
24897545

Key Documents

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biological source

Streptomyces nogalater

Assay

≥95%

form

solid

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

2-8°C

SMILES string

COC1C(C)OC(OC2CC(C)(O)C(C(=O)OC)c3cc4C(=O)c5c6OC7OC(C)(C(O)C(C7O)N(C)C)c6cc(O)c5C(=O)c4c(O)c23)C(OC)C1(C)OC

InChI

1S/C39H49NO16/c1-14-32(49-7)39(4,52-10)33(50-8)36(53-14)54-19-13-37(2,48)24(34(47)51-9)15-11-16-21(27(43)20(15)19)28(44)22-18(41)12-17-30(23(22)26(16)42)55-35-29(45)25(40(5)6)31(46)38(17,3)56-35/h11-12,14,19,24-25,29,31-33,35-36,41,43,45-46,48H,13H2,1-10H3

InChI key

KGTDRFCXGRULNK-UHFFFAOYSA-N

Biochem/physiol Actions

Anthracyclic antitumor antibiotic.
Anthracyclic antitumor antibiotic. It is used as a sequence specific DNA binding (intercalation) reagent, binds d(CGTACG), d(ATGCAT).

Other Notes

50mg
Keep container tightly closed in a dry and well-ventilated place.Light sensitive.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
080H4012

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Ruogu Peng et al.
Organic letters, 14(8), 1962-1965 (2012-04-07)
A novel reductive Heck cyclization approach was developed in order to construct a model DEF-benzoxocin ring system that is present in nogalamycin, menogaril, and related anthracycline antitumor antibiotics.
Azmiri Sultana et al.
Acta crystallographica. Section D, Biological crystallography, 60(Pt 6), 1118-1120 (2004-05-26)
Nogalonic acid methyl ester cyclase (SnoaL) catalyzes the last ring-closure step in the biosynthesis of the polyketide antibiotic nogalamycin. Crystals of a complex of SnoaL with the substrate nogalonic acid methyl ester have been obtained using PEG 4000 as precipitant.
Thadee Grocholski et al.
Biochemistry, 49(5), 934-944 (2010-01-08)
SnoaB is a cofactor-independent monooxygenase that catalyzes the conversion of 12-deoxynogalonic acid to nogalonic acid in the biosynthesis of the aromatic polyketide nogalamycin in Streptomyces nogalater. In vitro (18)O(2) experiments establish that the oxygen atom incorporated into the substrate is
Mikko Metsä-Ketelä et al.
Antimicrobial agents and chemotherapy, 47(4), 1291-1296 (2003-03-26)
The biosynthesis pathways of two anthracyclines, nogalamycin and aclacinomycin, were directed toward angucyclines by using an angucycline-specific cyclase, pgaF, isolated from a silent antibiotic biosynthesis gene cluster. Addition of pgaF to a gene cassette that harbored the early biosynthesis genes
Md Saimul Islam et al.
Journal of cellular physiology, 235(11), 8114-8128 (2020-01-22)
Triple negative breast cancer (TNBC) originates from a less differentiated ductal cell of breast, which is less sensitive to chemotherapy. The chemotolerance mechanism of TNBC has not yet been studied in detail. For this reason, molecular profiles (expression/genetic/epigenetic) of Y654-p-β-catenin
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