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Substance Name: Atractyloside
RN: 17754-44-8
UNII: H6WC6L09RM
InChIKey: IUCNQFHEWLYECJ-FNAJZLPOSA-L

Note

  • A glycoside of a kaurene type diterpene that is found in some plants including Atractylis gummifera (ATRACTYLIS); COFFEE; XANTHIUM, and CALLILEPIS. Toxicity is due to inhibition of ADENINE NUCLEOTIDE TRANSLOCASE.

Molecular Formula

  • C30-H46-O16-S2.2K

Molecular Weight

  • 802.9896
 

Classification Codes

  • Enzyme Inhibitors
  • Natural Product
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Names and Synonyms

Name of Substance

  • Atractyloside

MeSH Heading

  • Atractyloside

Synonyms

  • 15-Hydroxy-2-((2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl)oxy)-19-norkaur-16-en-18-oic acid dipotassium salt, (2beta,4alpha,15alpha)-
  • Atractylate de potassium
  • Atractylate de potassium [French]
  • Atractylin (C30 glucoside)
  • Attrattiloside
  • Attrattiloside [Italian]
  • EINECS 241-744-8
  • Potassium atractylate
  • UNII-H6WC6L09RM

Systematic Names

  • 19-Norkaur-16-en-18-oic acid, 15-hydroxy-2-((2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl)oxy)-, (2beta,4alpha,15alpha)-
  • 19-Norkaur-16-en-18-oic acid, 15-hydroxy-2-((2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-beta-D-glucopyranosyl)oxy)-, dipotassium salt, (2beta,4alpha,15alpha)-
  • Atractyloside
  • Dipotassium hydrogen 15alpha-hydroxy-2beta-((2-O-isovaleryl-3,4alpha-di-O-sulphonato-beta-D-glucopyranosyl)oxy)-19-norkaur-16-en-18-oate

Registry Numbers

CAS Registry Number

  • 17754-44-8

FDA UNII

  • H6WC6L09RM

System Generated Number

  • 0017754448

Molecular Formulas

Molecular Formula

  • C30-H46-O16-S2.2K

Molecular Formula Fragments

  • C30-H46-O16-S2
  • COMPONENT
  • K

Structure Descriptors

InChI

1S/C30H46O16S2.2K/c1-14(2)9-22(32)44-25-24(46-48(39,40)41)23(45-47(36,37)38)20(13-31)43-28(25)42-17-10-18(27(34)35)19-7-8-30-11-16(15(3)26(30)33)5-6-21(30)29(19,4)12-17;;/h14,16-21,23-26,28,31,33H,3,5-13H2,1-2,4H3,(H,34,35)(H,36,37,38)(H,39,40,41);;/q;2*+1/p-2/t16-,17-,18-,19-,20-,21+,23-,24+,25-,26+,28-,29-,30-;;/m1../s1

InChIKey

IUCNQFHEWLYECJ-FNAJZLPOSA-L

Smiles

CC(C)CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@@H]2C[C@H]([C@H]3CC[C@@]45C[C@@H](CC[C@H]4[C@@]3(C2)C)C(=C)[C@@H]5O)C(=O)O)CO)OS(=O)(=O)[O-])OS(=O)(=O)[O-].[K+].[K+]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intramuscular 431mg/kg (431mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Bolletino della Societe Italiana di Biologia Sperimentale. Vol. 44, Pg. 253, 1968.
rat LD50 intraperitoneal 143mg/kg (143mg/kg)   Archives of Toxicology. Vol. 32, Pg. 169, 1974.