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Substance Name: Helenalin
RN: 6754-13-8
UNII: 4GUY9L896T
InChIKey: ZVLOPMNVFLSSAA-XEPQRQSNSA-N

Note

  • Toxic principle of Helenium microcephalum (smallhead sneezeweed).

Molecular Formula

  • C15-H18-O4

Molecular Weight

  • 262.3032
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Antirheumatic Agents
  • Cardiotonic Agents
  • Cardiovascular Agents
  • Hematologic Agents
  • Mutation Data
  • Peripheral Nervous System Agents
  • Platelet Aggregation Inhibitors
  • Protective Agents
  • Sensory System Agents
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Names and Synonyms

Name of Substance

  • Helenalin

Synonyms

  • (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-Octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
  • 4-18-00-01434 (Beilstein Handbook Reference)
  • 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone
  • Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone
  • Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-
  • BRN 0028081
  • Helenalin
  • Helenalin A
  • HSDB 3490
  • NSC 85236
  • PF 56
  • UNII-4GUY9L896T

Systematic Names

  • Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone
  • Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone (8CI)
  • Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))- (9CI)

Registry Numbers

CAS Registry Number

  • 6754-13-8

FDA UNII

  • 4GUY9L896T

System Generated Number

  • 0006754138

Structure Descriptors

InChI

1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1

InChIKey

ZVLOPMNVFLSSAA-XEPQRQSNSA-N

Smiles

C[C@@H]1C[C@@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)O)C(=C)C(=O)O2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
domestic animals - goat/sheep LD50 oral 100mg/kg (100mg/kg)   Pharmazie in Unserer Zeit. Vol. 10, Pg. 1, 1981.
hamster LD50 oral 85mg/kg (85mg/kg)   Pharmazie in Unserer Zeit. Vol. 10, Pg. 1, 1981.
mouse LD50 intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: PERITONITIS
Research Communications in Chemical Pathology and Pharmacology. Vol. 28, Pg. 189, 1980.
mouse LD50 oral 150mg/kg (150mg/kg)   American Journal of Veterinary Research. Vol. 37, Pg. 859, 1976.
rabbit LD50 oral 90mg/kg (90mg/kg)   Pharmazie in Unserer Zeit. Vol. 10, Pg. 1, 1981.
rat LD50 oral 125mg/kg (125mg/kg)   Pharmazie in Unserer Zeit. Vol. 10, Pg. 1, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 167-168 deg C   EXP
log P (octanol-water) 0.87 (none)   EXP
Water Solubility 1.18E+04 mg/L 25 EST
Vapor Pressure 4.69E-09 mm Hg 25 EST
Henry's Law Constant 1.38E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.17E-10 cm3/molecule-sec 25 EST

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