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Namespace Prefixes

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n14http://linked.opendata.cz/resource/drugbank/drug/DB01051/identifier/chemspider/

Statements

Subject Item
n2:DB01051
rdf:type
n3:Drug
n3:description
An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189) [PubChem]
n3:generalReferences
# Vickers AA, Chopra I, O'neill AJ: Intrinsic novobiocin resistance in Staphylococcus saprophyticus. Antimicrob Agents Chemother. 2007 Sep 17;. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17876001 # Burlison JA, Neckers L, Smith AB, Maxwell A, Blagg BS: Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90. J Am Chem Soc. 2006 Dec 6;128(48):15529-36. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17132020 # Singh G, Jayanarayan KG, Dey CS: Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani. Mol Biochem Parasitol. 2005 May;141(1):57-69. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15811527 # CORBIN EE, PRIGOT A: Novobiocin; absorption, diffusion, and excretion studies. Antibiot Annu. 1956-1957;:392-5. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/13425410 # DAVID NA, BURGNER PR: Clinical effectiveness and safety of novobiocin. Antibiotic Med Clin Ther. 1956 Apr;2(4):219-29. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/13303117
n3:group
approved
n3:halfLife
6 hours
n3:indication
For the treatment of infections due to staphylococci and other susceptible organisms
owl:sameAs
n18:DB01051 n19:DB01051
dcterms:title
Novobiocin
adms:identifier
n9:NOV n10:9346 n11:DB01051 n12:C05080 n13:282 n14:8981 n16:46507250 n20:PA164768819 n21:Novobiocin
n3:mechanismOfAction
Novobiocin is an aminocoumarin. Aminocoumarins are very potent inhibitors of bacterial DNA gyrase and work by inhibiting the GyrB subunit of the enzyme involved in energy tranduction. Novobiocin as well as the other aminocoumarin antibiotics act as competitive inhibitors of the ATPase reaction catalysed by GyrB.
n3:synonym
N-{7-[(3-O-carbamoyl-6-deoxy-5-methyl-4-O-methyl-beta-D-gulopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-chromen-3-yl}-4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamide Novobiocina Novobiocine Novobiocin Novobiocinum
n3:mixture
n7:271B5B48-363D-11E5-9242-09173F13E4C5 n7:271B5B46-363D-11E5-9242-09173F13E4C5 n7:271B5B47-363D-11E5-9242-09173F13E4C5 n7:271B5B45-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
95%
n3:salt
n3:synthesisReference
Jon Thorson, "Glycorandomization and Production of Novel Novobiocin Analogs." U.S. Patent US20120264924, issued October 18, 2012.
n5:hasConcept
n6:M0015020
n3:IUPAC-Name
n4:271B5B4D-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5B53-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5B52-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5B4F-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5B50-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5B51-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5B63-363D-11E5-9242-09173F13E4C5 n4:271B5B4B-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5B64-363D-11E5-9242-09173F13E4C5 n4:271B5B49-363D-11E5-9242-09173F13E4C5 n4:271B5B4C-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5B4A-363D-11E5-9242-09173F13E4C5
n3:pKa
n4:271B5B65-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B5B59-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5B5A-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5B54-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5B55-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5B57-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5B56-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5B58-363D-11E5-9242-09173F13E4C5
n3:absorption
Oral bioavailability is negligible.
n3:affectedOrganism
Enteric bacteria and other eubacteria
n3:casRegistryNumber
303-81-1
n3:category
n3:Bioavailability
n4:271B5B5F-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5B61-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5B62-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5B5E-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5B5D-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5B60-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5B4E-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5B5B-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5B5C-363D-11E5-9242-09173F13E4C5