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Bis(monooleoylglycero)phosphate

Bis(monoacylglycero)phosphate (BMP)(lysobisphosphatidic acid (LBPA)) is a major phospholipid constituent of intralumenal membranes in late endosomes/lysosomes, where it regulates the degradation and sorting of lipid cargo || Ceroid lipofuscinosis neuronal protein 5 (CLN5) functions as a lysosomal transacylase that generates BMP by acylating lyso-phosphatidylglycerol but is not the only enzyme doing so. Synthetized from Dioleoylphosphatidylglycerol (PG) Hemi-Bis(monooleoylglycero)phosphate (HemiBMP) by LIPC LIPG LIPH

General

Type : Phospholipid, Phosphatidylglycerol, Diacylglycerol, Oleate

Chemical_Nomenclature : [(2S)-1-hydroxy-3-[hydroxy-[(2S)-3-hydroxy-2-[(Z)-octadec-9-enoyl]oxypropoxy]phosphoryl]oxypropan-2-yl] (Z)-octadec-9-enoate

Canonical SMILES : O([P](=O)(O)OCC(CO)OC(CCCCCCCC=CCCCCCCCC)=O)CC(COC(=O)CCCCCCCC=CCCCCCCCC)O

InChI : InChI=1S\/C42H79O10P\/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-36-39(44)37-50-53(47,48)51-38-40(35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2\/h17-20,39-40,43-44H,3-16,21-38H2,1-2H3,(H,47,48) || InChI=1S\/C42H79O10P\/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)51-39(35-43)37-49-53(47,48)50-38-40(36-44)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2\/h17-20,39-40,43-44H,3-16,21-38H2,1-2H3,(H,47,48)\/b19-17-,20-18-\/t39-,40-\/m0\/s1

InChIKey : BLPKWNZZIJINCN-UHFFFAOYSA-N || ZCXRIDHJRROVJY-JOZUOZHYSA-N

Other name(s) : BMP  ||  CHEBI:139156  ||  Bis-[2-(9Z-octadecenoyl)-3-lyso-sn-glycero]-1-phosphate  ||  LBPA(18:1(9Z)\/18:1(9Z))  ||  BMP(18:1(9Z)\/18:1(9Z))  ||  CHEBI:139541  ||  LMGP04100003

MW : 775.054

Formula : C42H79O10P

CAS_number :

PubChem : 11262814

UniChem : BLPKWNZZIJINCN-UHFFFAOYSA-N,    ZCXRIDHJRROVJY-JOZUOZHYSA-N

Target

Structures : No structure

Families : No family

References (2)

Title : Functionally overlapping intra- and extralysosomal pathways promote bis(monoacylglycero)phosphate synthesis in mammalian cells - Bulfon_2024_Nat.Commun_15_9937
Author(s) : Bulfon D , Breithofer J , Grabner GF , Fawzy N , Pirchheim A , Wolinski H , Kolb D , Hartig L , Tischitz M , Zitta C , Bramerdorfer G , Lass A , Taschler U , Kratky D , Greimel P , Zimmermann R
Ref : Nat Commun , 15 :9937 , 2024
Abstract :
PubMedSearch : Bulfon_2024_Nat.Commun_15_9937
PubMedID: 39548099

Title : Effect of lysosomal storage on bis(monoacylglycero)phosphate - Meikle_2008_Biochem.J_411_71
Author(s) : Meikle PJ , Duplock S , Blacklock D , Whitfield PD , Macintosh G , Hopwood JJ , Fuller M
Ref : Biochemical Journal , 411 :71 , 2008
Abstract :
PubMedSearch : Meikle_2008_Biochem.J_411_71
PubMedID: 18052935