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Substance Name: Novobiocin [INN:BAN]
RN: 303-81-1
UNII: 17EC19951N
InChIKey: YJQPYGGHQPGBLI-KGSXXDOSSA-N

Note

  • 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)

Molecular Formula

  • C31-H36-N2-O11

Molecular Weight

  • 612.6284
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Natural Product
  • Nucleic Acid Synthesis Inhibitors
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Names and Synonyms

Name of Substance

  • Novobiocin
  • Novobiocin [INN:BAN]

MeSH Heading

  • Novobiocin

Synonyms

  • 7-(3-(O-Carbamoyl)-4-(O-methyl)-5,5-dimethyl-alpha-L-lyxopyranosyloxy)-4-hydroxy-3-(4-hydroxy-3-(3-methyl-2-butenyl)benzamidol)-8-methylcumarin
  • 7-(Carbamoyltetrahydro-3-hydroxy-5-methoxy-6,6-dimethylpyran-2-yloxy)-4-hydroxy-3-(4-hydroxy-3-(3-methylbut-2-enyl)benzamide)-8-methyl-2H-chromen-2-one
  • AI3-50148
  • Albamix
  • Albamycin
  • Antibiotic PA-93
  • Cardelmycin
  • Cathocin
  • Cathomycin
  • Crystallinic acid
  • EINECS 206-146-3
  • HSDB 7443
  • Inamycin
  • Novo-R
  • Novobiocin
  • Novobiocina
  • Novobiocina [INN-Spanish]
  • Novobiocine
  • Novobiocine [INN-French]
  • Novobiocinum
  • Novobiocinum [INN-Latin]
  • PA 93
  • Robiocina
  • Sirbiocina
  • Spheromycin
  • Stilbiocina
  • Streptonivicin
  • U 6391
  • UNII-17EC19951N

Systematic Names

  • Benzamide, N-(7-((3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-beta-L-lyxo-hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-butenyl)-
  • Coumarin, 7-(4-(carbamoyloxy)tetrahydro-3-hydroxy-5-methoxy-6,6-dimethylpyran-2-yloxy)-4-hydroxy-3-(4-hydroxy-3-(4-hydroxy-3-(3-methyl-2-butenyl)benzamido)-8-methyl-
  • Novobiocin

Registry Numbers

CAS Registry Number

  • 303-81-1

FDA UNII

  • 17EC19951N

Related Registry Numbers

  • 1476-53-5 (mono-hydrochloride salt)
  • 4309-70-0 (calcium salt)

System Generated Number

  • 0000303811

Structure Descriptors

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(=O)N)[C@@H](O)[C@H](Oc2ccc3C(=C(NC(=O)c4ccc(O)c(CC=C(C)C)c4)C(=O)Oc3c2C)O)OC1(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo unreported 171mg/kg/12D- (171mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE
"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 137, 1978.
mouse LD50 intraperitoneal 262mg/kg (262mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 471, 1967.
mouse LD50 intravenous 407mg/kg (407mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 471, 1967.
mouse LD50 oral 1500mg/kg (1500mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 338, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 4.3 (none)   EXP
log P (octanol-water) 2.450 (none)   EST
Atmospheric OH Rate Constant 2.68E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.