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    Technical details about Jacobine, learn more about the structure, uses, toxicity, action, side effects and more

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    Jacobine

    REF. STANDARDS & IMPURITIES

    PharmaCompass

    Farmhispania Group, a leading European CDMO in HPAPI Technologies & High Potency Fermentation.

    One Pharma aims to be one of the leading generic companies in Europe.

    2D Structure
    1. Also known as: 6870-67-3, Ccris 5777, Hsdb 3500, Nsc 89936, Brn 0054580, Gm32u80h1r
    Molecular Formula
    C18H25NO6
    Molecular Weight
    351.4  g/mol
    InChI Key
    IAPHXJRHXBQDQJ-WKMWQDDRSA-N
    FDA UNII
    GM32U80H1R
    jacobine is a natural product found in Crotalaria micans, Senecio brasiliensis, and other organisms with data available.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,3'S,4S,6R,7R,17R)-7-hydroxy-3',6,7-trimethylspiro[2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-4,2'-oxirane]-3,8-dione
    2.1.2 InChI
    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
    2.1.3 InChI Key
    IAPHXJRHXBQDQJ-WKMWQDDRSA-N
    2.1.4 Canonical SMILES
    CC1CC2(C(O2)C)C(=O)OC3CCN4C3C(=CC4)COC(=O)C1(C)O
    2.1.5 Isomeric 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
    2.2 Other Identifiers
    2.2.1 UNII
    GM32U80H1R
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 6870-67-3

    2. Ccris 5777

    3. Hsdb 3500

    4. Nsc 89936

    5. Brn 0054580

    6. Gm32u80h1r

    7. Jacobine.

    8. Nsc-89936

    9. 471-14-7

    10. Jacobine [iarc]

    11. Jacobine , Hplc Grade

    12. Unii-gm32u80h1r

    13. 4-27-00-06827 (beilstein Handbook Reference)

    14. Chebi:6080

    15. Dtxsid501020078

    16. 15,20-epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione

    17. Mfcd00870079

    18. (15alpha,20r)15,20-epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione

    19. 12beta-hydroxy-12alpha,13beta-dimethylsenec-1-enine-15s-spiro-2'-(3'r-methyloxiran)

    20. Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20s)-

    21. Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15alpha,20r)-

    22. Hy-124058

    23. Cs-0084068

    24. Q27107031

    25. (15alpha,20r)15,20-epoxy-15,20-dihydro-12-hydroxy-senecionan-11,16-dione

    26. (2s,3s,5'r,6'r,9a1'r,14a'r)-6'-hydroxy-3,5',6'-trimethyl-5',6',9',9a1',11',13',14',14a'-octahydro-2'h-spiro[oxirane-2,3'-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine]-2',7'(4'h)-dione

    27. Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15.alpha.,20s)-

    28. Spiro((1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-3(2h),2'-oxirane)-2,7(4h)-dione, 5,6,9,11,13,14,14a,14b-octahydro-6-hydroxy-3',5,6-trimethyl-, (2's,3's,5r,6r,14ar,14br)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 351.4 g/mol
    Molecular Formula C18H25NO6
    XLogP30.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count0
    Exact Mass351.16818752 g/mol
    Monoisotopic Mass351.16818752 g/mol
    Topological Polar Surface Area88.6 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity648
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Warning

    The data suggest that consumption of milk from goats fed Senecio jacobaea produces a selective alteration of the activities of hepatic drug-metabolizing enzymes.

    PMID:7302964 Miranda C et al; Toxicol Lett 8(6): 343-7 (1981)

    5 Pharmacology and Biochemistry
    5.1 Absorption, Distribution and Excretion

    Excretion of pyrrolizidine alkaloids (pa's) in diet of rabbits was not affected by the addition of copper and zinc to the diet. Isolated pa's from Senecio jacobaea were found to be readily transferred across the mucosa of isolated everted sacs of jejunum and ileum in vitro against a concentration gradient. These results suggest that the effects of dietary Senecio jacobaea on alterations in mineral metabolism are not due to changes in GI mineral absorption. In addition, it appears that the resistance of rabbits to dietary Senecio jacobaea intoxication is not caused by low GI absorption of pyrrolizidine alkaloids, but rather by efficient urinary elimination.

    PMID:7161214 Swick R et al; J Anim Sci 55 (6): 1417 (1982)

    5.2 Metabolism/Metabolites

    In general, the hepatotoxic pyrrolidine alkaloids are metabolized in rat liver to give hydrolysis products, n-oxides and dehydropyrrolizidine (pyrrolic) deriv. The latter group appears on current evidence to mediate most of toxic reactions of alkaloids. These pyrrolic deriv are produced by mixed-function oxidases of liver cells. Initial product formed from alkaloids that are esters of...retronecine (eg, jacobine...) is very probably the dehydroalkaloid. Dehydroalkaloids are highly reactive alkylating agents which react immediately with cell constituents to give soluble or bound secondary metabolites or which hydrolyze to dehydroaminoalcohol. /pyrrolizidine alkaloids/

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 336 (1976)

    The effect of prolonged phenobarbital (pb) administration on the toxicity of Senecio jacobaea (sj) was studied in sheep. Results suggested that mixed-function oxidase induction by pb does not increase the susceptibility of sheep to sj intoxication. Sheep possess a high activity of hepatic microsomal epoxide hydrolase which could account for their resistance to sj intoxication.

    PMID:6853385 Swick R et al; J Anim Sci 56(4): 887 (1983)

    Comparison is made of the alkylating activities of a series of semi-synthetic pyrrole esters and pyrrole derivatives of pyrrolizidine alkaloids under pseudo-first-order reaction conditions. Data for alkylation by jacobine pyrrole (a reactive metabolite of jacobine) fit a simple first-order rate expression for product formation. The large increase in reaction rate for jacobine pyrrole is suggestive of an electronic field effect due to the epoxide ring in proximity to the C-7 ester moiety.

    Karchesy J et al; Heterocycles 16(4): 631 (1981)

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