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Substance Name: Periplocin
RN: 13137-64-9
UNII: 199X940O3K
InChIKey: KWBPKUMWVXUSCA-AXQDKOMKSA-N

Note

  • Isolated from Periploca calophylla.

Classification Code

  • Natural Product

Molecular Formula

  • C36-H56-O13

Molecular Weight

  • 696.8254
 
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Names and Synonyms

Name of Substance

  • Periplocin

Synonyms

  • 4-18-00-02439 (Beilstein Handbook Reference)
  • BRN 0075742
  • Glucoperiplocymarin
  • Periplocin
  • Periplocoside
  • Periplogenin + D-cymarose + D-glucose
  • Periplogenin + D-cymarose + D-glucose [German]
  • UNII-199X940O3K

Systematic Name

  • Card-20(22)-enolide, 3-((2,6-dideoxy-4-O-beta-D-glucopyranosyl-3-O-methyl-beta-D-ribo-hexopyranosyl)oxy)-5,14-dihydroxy-, (3-beta,5-beta)-

Registry Numbers

CAS Registry Number

  • 13137-64-9

FDA UNII

  • 199X940O3K

System Generated Number

  • 0013137649

Structure Descriptors

InChI

1S/C36H56O13/c1-18-31(49-32-30(41)29(40)28(39)25(16-37)48-32)24(44-4)14-27(46-18)47-20-5-9-33(2)22-6-10-34(3)21(19-13-26(38)45-17-19)8-12-36(34,43)23(22)7-11-35(33,42)15-20/h13,18,20-25,27-32,37,39-43H,5-12,14-17H2,1-4H3/t18-,20+,21-,22+,23-,24+,25-,27+,28-,29+,30-,31-,32+,33-,34-,35+,36+/m1/s1

InChIKey

KWBPKUMWVXUSCA-AXQDKOMKSA-N

Smiles

C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 120ug/kg (0.12mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

BEHAVIORAL: MUSCLE WEAKNESS
"Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 193, 1963.
cat LDLo subcutaneous 2500ug/kg (2.5mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 27, Pg. 449, 1926.
cat LDLo unreported 121ug/kg (0.121mg/kg)   "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 151, 1963.
frog LDLo subcutaneous 34mg/kg (34mg/kg) CARDIAC: PULSE RATE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of Pharmacology and Experimental Therapeutics. Vol. 27, Pg. 449, 1926.
rabbit LDLo subcutaneous 10mg/kg (10mg/kg) BEHAVIORAL: TREMOR

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 27, Pg. 449, 1926.
rat LDLo subcutaneous 480mg/kg (480mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 27, Pg. 449, 1926.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.880 (none)   EST
Water Solubility 8000 mg/L 20 EXP
Atmospheric OH Rate Constant 2.10E-10 cm3/molecule-sec 25 EST

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