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Chemistry

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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
jacobine is a natural product found in Crotalaria micans, Senecio brasiliensis, and other organisms with data available.
1 2D Structure

Jacobine

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)


REF. STANDARDS & IMPURITIES

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Looking for 6870-67-3 / Jacobine API manufacturers, exporters & distributors?

Jacobine manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Jacobine API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Jacobine manufacturer or Jacobine supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Jacobine manufacturer or Jacobine supplier.

PharmaCompass also assists you with knowing the Jacobine API Price utilized in the formulation of products. Jacobine API Price is not always fixed or binding as the Jacobine Price is obtained through a variety of data sources. The Jacobine Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Jacobine

Synonyms

6870-67-3, Ccris 5777, Hsdb 3500, Nsc 89936, Brn 0054580, Gm32u80h1r

Cas Number

6870-67-3

Unique Ingredient Identifier (UNII)

GM32U80H1R

About Jacobine

jacobine is a natural product found in Crotalaria micans, Senecio brasiliensis, and other organisms with data available.

Jacobine Manufacturers

A Jacobine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Jacobine, including repackagers and relabelers. The FDA regulates Jacobine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Jacobine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Jacobine Suppliers

A Jacobine supplier is an individual or a company that provides Jacobine active pharmaceutical ingredient (API) or Jacobine finished formulations upon request. The Jacobine suppliers may include Jacobine API manufacturers, exporters, distributors and traders.

Jacobine GMP

Jacobine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Jacobine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Jacobine GMP manufacturer or Jacobine GMP API supplier for your needs.

Jacobine CoA

A Jacobine CoA (Certificate of Analysis) is a formal document that attests to Jacobine's compliance with Jacobine specifications and serves as a tool for batch-level quality control.

Jacobine CoA mostly includes findings from lab analyses of a specific batch. For each Jacobine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Jacobine may be tested according to a variety of international standards, such as European Pharmacopoeia (Jacobine EP), Jacobine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Jacobine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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