Cyclipostin

Ten inhibitors of HSL, termed cyclipostins, have been isolated from the mycelium of Streptomyces species DSM 13381. Phosphate esters of long chain lipophilic alcohols. All members of the Cyclipostins family are very potent inhibitors of hormone-sensitive lipase (HSL) a therapeutic target for type II diabetes. The different Cyclopostins are: Cyclipostin P; CID 101182228; LXXPVFWDVXTYTB-BPADPFCFSA-N; (1beta)-4beta-(Hexadecyloxy)-6-methyl-8-oxo-3,5,9-trioxa-4-phosphabicyclo[5.3.0]deca-6-ene 4-oxide; (6S)-6alpha-(Hexadecyloxy)-8-methyl-3,3abeta-dihydro-1H,4H,6H-2,5,7-trioxa-6-phosphaazulene-1-one 6-oxide --- Cyclipostin P2; Cyclipostin P 2; IGWOOZHLAHUMBM-BPADPFCFSA-N; CID 101182229 --- Cyclipostin T; CID 101182233; UEXFAQDUVJPKAX-GFTAOQHMSA-N --- Cyclipostin S; CID 101182232; NESUOKQUVWDIJP-UBIBJYAGSA-N --- Cyclipostin R; CID 101182230; BHKGHKHKDXVQJF-CUXXENAFSA-N --- Cyclipostin N; CID 101182227; YNKNWOLTEQUDMB-OJQMSQGESA-N --- Cyclipostin F; CID 101182226; AEULNKPXALBIHK-DXHYANOHSA-N --- Cyclipostin A; CID 101182225; JGTUCPMGHURLJI-FRMQRXHYSA-N --- Cyclipostin T2; CID 101182234; SYOULUNKPBFPTF-GFTAOQHMSA-N --- trans-Cyclipostin P; CID 101805205; LXXPVFWDVXTYTB-UHWFRNQFSA-N

General

Type : Organophosphate, Cyclic OP

Chemical_Nomenclature : (8aR)-3-hexadecoxy-5-methyl-3-oxido-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-3-ium-6-one

Canonical SMILES :

InChI : InChI=1S\/C23H41O6P\/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27-30(25)28-19-21-18-26-23(24)22(21)20(2)29-30\/h21H,3-19H2,1-2H3\/t21-,30?\/m1\/s1

InChIKey : LXXPVFWDVXTYTB-BPADPFCFSA-N

Other name(s) : (3aR,6R)-3-R1-5-R2-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one


MW :

Formula :

CAS_number :

PubChem : 101182228

UniChem : LXXPVFWDVXTYTB-BPADPFCFSA-N

Target

Families : Cyclipostin ligand of proteins in family
Hormone-sensitive_lipase_like

References (4)

Title : Cyclophostin and Cyclipostins analogues, new promising molecules to treat mycobacterial-related diseases - Nguyen_2018_Int.J.Antimicrob.Agents_51_651
Author(s) : Nguyen PC , Madani A , Santucci P , Martin BP , Paudel RR , Delattre S , Herrmann JL , Spilling CD , Kremer L , Canaan S , Cavalier JF
Ref : Int J Antimicrob Agents , 51 :651 , 2018
PubMedID: 29241819

Title : Rat hormone sensitive lipase inhibition by cyclipostins and their analogs - Vasilieva_2015_Bioorg.Med.Chem_23_944
Author(s) : Vasilieva E , Dutta S , Malla RK , Martin BP , Spilling CD , Dupureur CM
Ref : Bioorganic & Medicinal Chemistry , 23 :944 , 2015
PubMedID: 25678014
Gene_locus related to this paper: ratno-hslip

Title : The first total synthesis of (+\/-)-cyclophostin and (+\/-)-cyclipostin P: inhibitors of the serine hydrolases acetyl cholinesterase and hormone sensitive lipase - Malla_2011_Org.Lett_13_3094
Author(s) : Malla RK , Bandyopadhyay S , Spilling CD , Dutta S , Dupureur CM
Ref : Org Lett , 13 :3094 , 2011
PubMedID: 21591624

Title : Cyclipostins, novel hormone-sensitive lipase inhibitors from Streptomyces sp. DSM 13381. II. Isolation, structure elucidation and biological properties - Vertesy_2002_J.Antibiot.(Tokyo)_55_480
Author(s) : Vertesy L , Beck B , Bronstrup M , Ehrlich K , Kurz M , Muller G , Schummer D , Seibert G
Ref : J Antibiot (Tokyo) , 55 :480 , 2002
PubMedID: 12139017