Structure via PubChem · Public domain (PubChem)
novobiocin
Sign in to saveAlso known as 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
Novobiocin, also known as albamycin, is an aminocoumarin antibiotic that is produced by the actinomycete Streptomyces niveus, which is a heterotypic synonym for S. spheroides a member of the class Actinomycetia. Other aminocoumarin antibiotics include clorobiocin and coumermycin A1. Novobiocin was first reported in the mid-1950s (then called streptonivicin).
Chemical data
- Formula
- C31H36N2O11
- Molecular weight
- 612.6 g/mol
- IUPAC name
- [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate
- SMILES
- CC1=C(C=CC2=C1OC(=O)C(=C2O)NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)O[C@H]4[C@@H]([C@@H]([C@H](C(O4)(C)C)OC)OC(=O)N)O
- InChIKey
- YJQPYGGHQPGBLI-KGSXXDOSSA-N
- XLogP
- 3.3
- Polar surface area
- 196 Ų
- H-bond donors
- 5
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1964
- Admin. routes
- oral
- Indications
- osteomyelitis
via ChEMBL · EBI
Research
3,600 papers- Novobiocin Analogs as Potential Anticancer Agents.Mini reviews in medicinal chemistry · 2017
- Novobiocin.Progress in industrial microbiology · 1961
- Vancomycin and novobiocin.The Medical clinics of North America · 1970
- NOVOBIOCIN.Quarterly review of pediatrics · 1956
- [Novobiocin].Il Farmaco; edizione scientifica · 1956
via PubMed
Wikidata facts
- Mass
- 612.232
- Has use
- medication
Show 5 more facts
- chemical formula
- C₃₁H₃₆N₂O₁₁
- canonical SMILES
- CC1=C(C=CC2=C1OC(=O)C(=C2O)NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)OC4C(C(C(C(O4)(C)C)OC)OC(=O)N)O
- isomeric SMILES
- CC1=C(C=CC2=C1OC(=O)C(=C2O)NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)O[C@H]4[C@@H]([C@@H]([C@H](C(O4)(C)C)OC)OC(=O)N)O
- subject has role
- DNA polymerase inhibitors
- Commons category
- Novobiocin
via Wikidata · CC0
~8 min read
Encyclopedic overview
7 sectionsContents
- Clinical use
- Mechanism of action
- Structure
- Structure–activity relationship
- Biosynthesis
- References
- External links
Novobiocin, also known as albamycin, is an aminocoumarin antibiotic that is produced by the actinomycete Streptomyces niveus, which is a heterotypic synonym for S. spheroides a member of the class Actinomycetia. Other aminocoumarin antibiotics include clorobiocin and coumermycin A1. Novobiocin was first reported in the mid-1950s (then called streptonivicin).
==Clinical use== It is active against Staphylococcus epidermidis and may be used to differentiate S. epidermidis from coagulase-negative Staphylococcus saprophyticus, which is resistant to novobiocin, in culture.
Excerpted from Wikipedia’s “novobiocin” article, available under the CC BY-SA 4.0 licence.