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Substance Name: Glaucarubin
RN: 1448-23-3
UNII: EH6H7VS52J
InChIKey: LZKVXMYVBSNXER-YZPKDWIXSA-N

Note

  • (1 beta,2 alpha,11 beta,12 alpha,15 beta(S))-11,20-Epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-en-16-one. A quassinoid (Simaroubolide) from Simaruba glauca, a tropical shrub. It has been used as an antiamebic agent and is found to be cytotoxic. It may be of use in cancer chemotherapy.

Molecular Formula

  • C25-H36-O10

Molecular Weight

  • 496.5494
 

Classification Codes

  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Drug / Therapeutic Agent
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Names and Synonyms

Name of Substance

  • Glaucarubin

MeSH Heading

  • Glaucarubin

Synonyms

  • alpha-Kirondrin
  • Glarubin
  • Glaucarubin
  • Glaucarubina
  • Glaumeba
  • MK-53
  • NSC 14975
  • Simarubaceae
  • UNII-EH6H7VS52J

Systematic Names

  • Butyric acid, 2-hydroxy-2-methyl-, 4-ester with 1,2,3,3a-beta,4,6a-beta,7,7a-alpha,10,11,11a,11b-alpha-dodecahydro-1-alpha,2-alpha,4-beta,10-alpha,11-beta-pentahydroxy-3-alpha,8,11a-beta-trimethyl-5H-1,11c-beta-(epoxymethano)phenanthro(10,1-bc)pyran-5-one
  • Picras-3-en-16-one, 11,20-epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)-, (1beta,2alpha,11beta,12alpha,15beta(S))-

Registry Numbers

CAS Registry Number

  • 1448-23-3

FDA UNII

  • EH6H7VS52J

Other Registry Numbers

  • 1392-07-0
  • 1392-08-1

System Generated Number

  • 0001448233

Structure Descriptors

InChI

1S/C25H36O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-18,20,26-28,31-32H,6,8-9H2,1-5H3/t11-,12+,13+,14-,15-,16-,17-,18-,20-,22+,23-,24+,25+/m1/s1

InChIKey

LZKVXMYVBSNXER-YZPKDWIXSA-N

Smiles

C1[C@@]23[C@@H]4[C@@]5([C@@H](C(=C[C@@H]([C@H]5O)O)C)C[C@@H]3OC([C@@H]([C@@H]2[C@@H](C)[C@H]([C@@]4(O)O1)O)OC([C@@](CC)(C)O)=O)=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1200mg/kg (1200mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 114, Pg. 307, 1958.
mouse LD50 subcutaneous 28mg/kg (28mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 172, 1982.
rat LD50 oral 800mg/kg (800mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 172, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -1.080 (none)   EST
Water Solubility 1800 mg/L   EXP
Atmospheric OH Rate Constant 1.68E-10 cm3/molecule-sec 25 EST

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