Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Lupulon
RN: 468-28-0
UNII: B7425USG94
InChIKey: WPVSVIXDXMNGGN-UHFFFAOYSA-N

Note

  • Antibiotic from hops.

Classification Code

  • Natural Product

Molecular Formula

  • C26-H38-O4

Molecular Weight

  • 414.582
 
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Lupulon

Synonyms

  • 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-4-isovaleryl-2,6,6-tris(3-methyl-2-butenyl)-
  • 3,5-Dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
  • B'' -Acid
  • beta-Bitter acid
  • beta-Lupulic acid
  • EINECS 207-405-3
  • Lupulon
  • UNII-B7425USG94

Systematic Names

  • 3,5-Dihydroxy-2,6,6-tris(3-methylbuten-2-yl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
  • Lupulone

Registry Numbers

CAS Registry Number

  • 468-28-0

FDA UNII

  • B7425USG94

System Generated Number

  • 0000468280

Structure Descriptors

InChI

1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28,30H,10,13-15H2,1-8H3

InChIKey

WPVSVIXDXMNGGN-UHFFFAOYSA-N

Smiles

C1(=C(C(C\C=C(\C)C)(C\C=C(\C)C)C(C(=C1O)C\C=C(\C)C)=O)O)C(CC(C)C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 130mg/kg (130mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 281, 1949.
mouse LD50 intramuscular 600mg/kg (600mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 281, 1949.
mouse LD50 oral 525mg/kg (525mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 79, 1967.
mouse LD50 subcutaneous 600mg/kg (600mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 39, 1982.
rabbit LDLo oral 1gm/kg (1000mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 82, Pg. 1, 1950.
rat LD50 intramuscular 330mg/kg (330mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 8, Pg. 281, 1949.
rat LD50 oral 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 79, 1967.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 93 deg C   EXP
log P (octanol-water) 7.130 (none)   EST
Atmospheric OH Rate Constant 5.62E-10 cm3/molecule-sec 25 EST

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