Nogalamycin
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Nogalamycin
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CAS No:
1404-15-5
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Formula:
C39H49NO16
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Chemical Name:
Nogalamycin
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Synonyms:
2,6-Epoxy-2H-naphthaceno[1,2-b]oxocin-14-carboxylic acid,11-[(6-deoxy-3-C-methyl-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-4-(dimethylamino)-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-,methyl ester,(2R,3S,4R,5R,6R,11S,13S,14R)-;Nogalamycin;2,6-Epoxy-2H-naphthaceno[1,2-b]oxocin-14-carboxylic acid,11-[(6-deoxy-3-C-methyl-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-4-(dimethylamino)-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-,methyl ester,[2R-(2α,3β,4α,5β,6α,11β,13α,14α)]-;NSC 70845;U 15167;Antibiotic 205t3;11076-70-3;1263312-59-9
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CAS No:
Description
An anthrocycline from a Streptomyces nogalater variant. It is a cytolytic antineoplastic that inhibits DNA-dependent RNA synthesis by binding to DNA.
Characteristics
229
1.13800
1.2095 (rough estimate)
195-196 °C (decomp)
658.61°C (rough estimate)
498.1ºC
1.7650 (estimate)
LD50 in mice (mg/kg): 11.75 i.v., 4.79 i.p. (Hadidian)
Safety Information
NONH for all modes of transport
3
45-46-61-20/21/22
53-22-36/37/39-45
RA4550000
T
P201-P280-P308 + P313
H302-H312-H332-H350-H360
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)|Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA. (See all compounds classified as Intercalating Agents.)
Nogalamycin
Nogalamycin Use and Manufacturing
Nogalamycin is an unusual anthracycline produced by Streptomyces nogalater var. nogalater, reported by researchers at Upjohn in 1965. Nogalamycin contains two saccharides. The neutral monosaccharide attaches to the D ring, similar to the aminoglycoside moieties of the doxorubicin class, while the second, basic saccharide attaches to the phenolic group on the A ring in the ortho position to form a unique family of hexacyclic anthracyclines. Nogalamycin is potent antibacterial and antitumor agent
Computed Properties
Molecular Weight:787.8
XLogP3:1.1
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:17
Rotatable Bond Count:8
Exact Mass:787.30513448
Monoisotopic Mass:787.30513448
Topological Polar Surface Area:229
Heavy Atom Count:56
Complexity:1530
Undefined Atom Stereocenter Count:13
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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