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Substance Name: Jacobine
RN: 6870-67-3
InChIKey: IAPHXJRHXBQDQJ-WKMWQDDRSA-N

Molecular Formula

  • C18-H25-N-O6

Molecular Weight

  • 351.3965
 

Classification Codes

Classification Codes

  • Drug / Therapeutic Agent
  • Mutation Data
  • Natural Product
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3
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Names and Synonyms

Name of Substance

  • Jacobine

Synonyms

  • (15alpha,20R)15,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione
  • 12beta-Hydroxy-12alpha,13beta-dimethylsenec-1-enine-15S-spiro-2'-(3'R-methyloxiran)
  • 15,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione
  • 4-27-00-06827 (Beilstein Handbook Reference)
  • BRN 0054580
  • CCRIS 5777
  • HSDB 3500
  • Jacobine
  • NSC 89936
  • Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15alpha,20R)-

Systematic Names

  • (15alpha,20R)15,20-Epoxy-15,20-dihydro-12-hydroxy-senecionan-11,16-dione
  • Jacobine
  • Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20S)- (9CI)

Superlist Name

  • Jacobine

Registry Numbers

CAS Registry Number

  • 6870-67-3

Other Registry Number

  • 471-14-7

System Generated Number

  • 0006870673

Structure Descriptors

InChI

1S/C18H25NO6/c1-10-8-18(11(2)25-18)16(21)24-13-5-7-19-6-4-12(14(13)19)9-23-15(20)17(10,3)22/h4,10-11,13-14,22H,5-9H2,1-3H3/t10-,11+,13-,14-,17-,18+/m1/s1

InChIKey

IAPHXJRHXBQDQJ-WKMWQDDRSA-N

Smiles

C[C@@H]1C[C@]2([C@@H](O2)C)C(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@]1(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 77mg/kg (77mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 69, 1942.
rat LD50 unreported 60mg/kg (60mg/kg)   Cancer Research. Vol. 28, Pg. 2237, 1968.