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Isatidine

Isatidine

Synopsis, Chemistry

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Also known as: Retrorsine n-oxide, 15503-86-3, (5r,6s,9a1r,14ar,z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-2,7-dioxo-3,4,5,6,7,9,9a1,11,12,13,14,14a-dodecahydro-2h-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide, [1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3z,5r,6s,14ar,14br)-, Chebi:5977, Dtxsid4020747

Molecular Formula

C₁₈H₂₅NO₇

Molecular Weight

367.4 g/mol

InChI Key

IDIMIWQPUHURPV-WTWIWYCDSA-N

1 2D Structure

Isatidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

2.1.2 InChI

InChI=1S/C18H25NO7/c1-3-12-8-11(2)18(23,10-20)17(22)25-9-13-4-6-19(24)7-5-14(15(13)19)26-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-,19?/m1/s1

2.1.3 InChI Key

IDIMIWQPUHURPV-WTWIWYCDSA-N

2.1.4 Canonical SMILES

CC=C1CC(C(C(=O)OCC2=CC[N+]3(C2C(CC3)OC1=O)[O-])(CO)O)C

2.1.5 Isomeric SMILES

C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(CO)O)C

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Ret-no

2. Retrorsine N-oxide

2.2.2 Depositor-Supplied Synonyms

1. Retrorsine N-oxide

2. 15503-86-3

3. (5r,6s,9a1r,14ar,z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-2,7-dioxo-3,4,5,6,7,9,9a1,11,12,13,14,14a-dodecahydro-2h-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide

4. [1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3z,5r,6s,14ar,14br)-

5. Chebi:5977

6. Dtxsid4020747

7. Retrorsine-n-oxide , Hplc Grade

8. Zinc4098666

9. Mfcd00074872

10. Hy-116832

11. Cs-0066628

12. Q27106956

13. (3z,5r,6s,14ar,14br)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione 12-oxide

2.3 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₅NO₇
Molecular Weight	367.4 g/mol
XLogP3	0
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	1
Exact Mass	367.16310214 g/mol
Monoisotopic Mass	367.16310214 g/mol
Topological Polar Surface Area	111 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	673
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Metabolism/Metabolites

Isatidine is not converted into pyrrolic metabolites by isolated rat liver microsomes. It is, However, reduced to retrorsine in the intestinal tract of rats, possibly by the gut flora, thus accounting for the large increase in toxicity when isatidine is administered by mouth rather than parenterally.

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 272 (1976)

4.2 Mechanism of Action

Levels of pyrrolic metabolites bound to liver tissues and responsible for hepatotoxicity in rats given pyrrolizidine alkaloids did not reflect rates of formation of such metabolites measured in vitro. In animals, additional factors could influence formation and tissue binding of pyrrolic metabolites, including detoxication of alkaloids by hydrolysis and chemical reactivity and stability of toxic metabolites.

PMID:6825198 Mattocks A et al;Chem-Biol Interact 43(2): 209 (1983)