lipstatin lipstatin lipstatin is a potent, irreversible inhibitor of pancreatic lipase. it is a natural product that was first isolated from the actinobacterium streptomyces toxytricini. lipstatin names systematic iupac name (2s,4z,7z)-1-trideca-4,7-dien-2-yl (2s)-2-formamido-4-methylpentanoate other names (2s,4z,7z)-1--4,7-tridecadien-2-yl n-formyl-l-leucinate identifiers cas number 96829-59-3 y 3d model (jsmol) interactive image chemspider 7981411 y echa infocard 100.126.007 mesh lipstatin pubchem cid 9805651 unii ubd38w8lew y comptox dashboard (epa) dtxsid50897604 inchi inchi=1s/c29h49no5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h12-13,15-16,22-27h,5-11,14,17-21h2,1-4h3,(h,30,31)/b13-12-,16-15-/t24-,25-,26-,27-/m0/s1 ykey: oqmakwgyqljjia-cuoopaiesa-n yinchi=1/c29h49no5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h12-13,15-16,22-27h,5-11,14,17-21h2,1-4h3,(h,30,31)/b13-12-,16-15-/t24-,25-,26-,27-/m0/s1key: oqmakwgyqljjia-cuoopaiebu smiles o=c(o(c1oc(=o)1cccccc)c\c=c/c\c=c/ccccc)(nc=o)cc(c)c properties chemical formula c29h49no5 molar mass 491.713 g·mol−1 except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references the popular antiobesity drug orlistat (trade names xenical and alli) is a saturated derivative of lipstatin. biosynthesis lipstatin biosynthesis pathway in streptomyces toxytricini. lipstatin is composed of a 2-hexyl-3,5-dihydroxy-7,10-hexadecadienoic-β-lactone 22 carbon backbone from fatty acid synthesis pathway and an n-formyl-l-leucine group ester linked to the 5-hydroxyl group of the back bone. the composts of the lipstatin are ultimately from linoleic acid, octanoic acid, and l-leucine. the 22 carbon β-lactone moiety is derived from claisen condensation between 3-hydroxytetradeca-5,8-dienyl-coa derived from linoleic acid and hexyl-malonyl-acp derived from octanoic acid. linoleic acid is first attached to coa through some acyl-coa synthetase homologue synthesized by lipstatin biosynthetic operons (lst) and goes through two β-oxidation to hydroxytetradeca-5,8-dienyl-coa. 3’ hydroxyl group from solution h2o is added by enoyl reductase homologue followed by enoyl hydratase homologue. octanoic acid is also attached to coa through similar acyl-coa synthetase homologue (lstc) to form octanoyl-coa. octanoyl-coa is 2’ carboxylated and loaded to acyl carrier protein (acp) borrowed from primary metabolism to form hexyl-malonyl-acp. the β-lactone ring is formed by reduction of 3-keto group by 3-hydroxysteroid dehydrogenase homologue followed by a spontaneously nucleophilic attack of the 3-hydroxyl group on the carbonyl of the acp-tether acyl intermediate. this step follows the esterification of the n-formyl-l-leucine group. the n-formyl-l-leucine group is derived from l-leucine. l-leucine was activated by lste forming thioester and its α-amine group is formylated by lstf. finally, 5-hydroxyl of 22 carbon β-lactone backbone nucleophilic attacks on the acyl carbon of the formyl-leucine and forms the lipstatin.