novobiocin (CHEBI:28368)

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CHEBI:28368 - novobiocin

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ChEBI Name	novobiocin

ChEBI ID	CHEBI:28368

Definition	A coumarin-derived antibiotic obtained from Streptomyces niveus.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44505, CHEBI:7644, CHEBI:25597

Supplier Information	ChemicalBook:CB4500553, eMolecules:4800517, ZINC000014879999

Download	Molfile XML SDF

more structures >>

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M END): 20 ms

reading 80 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

80 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Formula

C31H36N2O11

Net Charge

Average Mass

612.62430

Monoisotopic Mass

612.23191

InChI

InChI=1S/C31H36N2O11/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37)/t23-,25+,26-,29-/m1/s1

InChIKey

YJQPYGGHQPGBLI-KGSXXDOSSA-N

SMILES

CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2C)OC1(C)C

Metabolite of Species	Details
Streptomyces niveus (NCBI:txid193462)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria.

Application(s):	hepatoprotective agent Any compound that is able to prevent damage to the liver.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	novobiocin (CHEBI:28368) has role Escherichia coli metabolite (CHEBI:76971) novobiocin (CHEBI:28368) has role antibacterial agent (CHEBI:33282) novobiocin (CHEBI:28368) has role antimicrobial agent (CHEBI:33281) novobiocin (CHEBI:28368) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750) novobiocin (CHEBI:28368) has role hepatoprotective agent (CHEBI:62868) novobiocin (CHEBI:28368) is a carbamate ester (CHEBI:23003) novobiocin (CHEBI:28368) is a ether (CHEBI:25698) novobiocin (CHEBI:28368) is a hexoside (CHEBI:35313) novobiocin (CHEBI:28368) is a hydroxycoumarin (CHEBI:37912) novobiocin (CHEBI:28368) is a monocarboxylic acid amide (CHEBI:29347) novobiocin (CHEBI:28368) is a monosaccharide derivative (CHEBI:63367) novobiocin (CHEBI:28368) is a phenols (CHEBI:33853) novobiocin (CHEBI:28368) is conjugate acid of novobiocin(1−) (CHEBI:71339)

Incoming	novobiocin(1−) (CHEBI:71339) is conjugate base of novobiocin (CHEBI:28368)

INNs	Sources
novobiocina	DrugBank
novobiocine	DrugBank
novobiocinum	DrugBank

Synonyms	Sources
N-{7-[(3-O-carbamoyl-6-deoxy-5-methyl-4-O-methyl-β-D-gulopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-chromen-3-yl}-4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamide	ChEBI
Novobiocin	KEGG COMPOUND

Manual Xrefs	Databases
1974	DrugCentral
C00002487	KNApSAcK
C05080	KEGG COMPOUND
DB01051	DrugBank
HMDB0015185	HMDB
LSM-5910	LINCS
NOV	PDBeChem
WO2012049521	Patent
WO2012103487	Patent
View more database links

Registry Numbers	Types	Sources
1445842	Reaxys Registry Number	Reaxys
303-81-1	CAS Registry Number	KEGG COMPOUND
303-81-1	CAS Registry Number	ChemIDplus

Citations

Garg G, Zhao H, Blagg BS (2017)
Design, synthesis and biological evaluation of alkylamino biphenylamides as Hsp90 C-terminal inhibitors.
Bioorganic & medicinal chemistry 25, 451-457 [PubMed:27914946]
[show Abstract]

Jakopin Ž, Ilaš J, Barančoková M, Brvar M, Tammela P, Sollner Dolenc M, Tomašič T, Kikelj D (2017)
Discovery of substituted oxadiazoles as a novel scaffold for DNA gyrase inhibitors.
European journal of medicinal chemistry 130, 171-184 [PubMed:28246042]
[show Abstract]

Bonanno L, Delubac B, Michel V, Auvray F (2017)
Influence of Stress Factors Related to Cheese-Making Process and to STEC Detection Procedure on the Induction of Stx Phages from STEC O26:H11.
Frontiers in microbiology 8, 296 [PubMed:28316592]
[show Abstract]

Petrushenko ZM, Zhao H, Zgurskaya HI, Rybenkov VV (2016)
Novobiocin Susceptibility of MukBEF-Deficient Escherichia coli Is Combinatorial with Efflux and Resides in DNA Topoisomerases.
Antimicrobial agents and chemotherapy 60, 2949-2953 [PubMed:26926630]
[show Abstract]

Moreira LB, Maranho LA, Baena-Nogueras RM, Lara-Martín PA, Martín-Díaz ML (2016)
Effects of novobiocin and methotrexate on the benthic amphipod Ampelisca brevicornis exposed to spiked sediments.
Marine environmental research 122, 169-177 [PubMed:27829510]
[show Abstract]

Chen W, Wang D, Zhou W, Sang H, Liu X, Ge Z, Zhang J, Lan L, Yang CG, Chen H (2016)
Novobiocin binding to NalD induces the expression of the MexAB-OprM pump in Pseudomonas aeruginosa.
Molecular microbiology 100, 749-758 [PubMed:26844397]
[show Abstract]

Pridgeon JW, Yildirim-Aksoy M, Klesius PH, Srivastava KK, Reddy PG (2012)
Attenuation of a virulent Aeromonas hydrophila with novobiocin and pathogenic characterization of the novobiocin-resistant strain.
Journal of applied microbiology 113, 1319-1328 [PubMed:22897434]
[show Abstract]

Angehrn P, Goetschi E, Gmuender H, Hebeisen P, Hennig M, Kuhn B, Luebbers T, Reindl P, Ricklin F, Schmitt-Hoffmann A (2011)
A new DNA gyrase inhibitor subclass of the cyclothialidine family based on a bicyclic dilactam-lactone scaffold. Synthesis and antibacterial properties.
Journal of medicinal chemistry 54, 2207-2224 [PubMed:21388139]
[show Abstract]

Duan P, You G (2009)
Novobiocin is a potent inhibitor for human organic anion transporters.
Drug metabolism and disposition: the biological fate of chemicals 37, 1203-1210 [PubMed:19282394]
[show Abstract]

Dangel V, Härle J, Goerke C, Wolz C, Gust B, Pernodet JL, Heide L (2009)
Transcriptional regulation of the novobiocin biosynthetic gene cluster.
Microbiology (Reading, England) 155, 4025-4035 [PubMed:19762445]
[show Abstract]

Wu LX, Xu JH, Zhang KZ, Lin Q, Huang XW, Wen CX, Chen YZ (2008)
Disruption of the Bcr-Abl/Hsp90 protein complex: a possible mechanism to inhibit Bcr-Abl-positive human leukemic blasts by novobiocin.
Leukemia 22, 1402-1409 [PubMed:18418407]
[show Abstract]

Burlison JA, Neckers L, Smith AB, Maxwell A, Blagg BS (2006)
Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90.
Journal of the American Chemical Society 128, 15529-15536 [PubMed:17132020]
[show Abstract]

Lührmann A, Thölke J, Behn I, Schumann J, Tiegs G, Hauschildt S (1998)
Immunomodulating properties of the antibiotic novobiocin in human monocytes.
Antimicrobial agents and chemotherapy 42, 1911-1916 [PubMed:9687383]
[show Abstract]

Shane SJ (1956)
Novobiocin, a New Antibiotic.
Canadian Medical Association journal 75, 51-52 [PubMed:20325309]

Last Modified

27 March 2017

ChEBI

CHEBI:28368 - novobiocin

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