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).
In the Vinony graph
Vinony's link graph records 310 inbound references to novobiocin, and connects out to microbiological culture, antibiotic and growth medium.
Vinony files it under 4-Hydroxyphenyl compounds, Antibiotics and Benzamides.
Vinony links it to 13 Wikipedia language editions.
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Withdrawn- Max clinical phase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.