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 || Bis(monoacylglycerol)phosphate (BMP) is a phospholipid crucial for lipid degradation and sorting in acidic organelles. Genetic and drug-induced lysosomal storage disorders (LSD) are associated with increased BMP concentrations in tissues and in the circulation BMP is found in intraluminal vesicles (ILVs) of late endosomes and lysosomes playing an important role for their structure and function. BMP is resistant to degradation by acid phospholipases and forms a docking station for lysosomal proteins. Lysosomal storage disorders (Niemann Pick disease, neuronal ceroid lipofuscinoses, Wolman disease) are associated with BMP accumulation in tissues. ABHD6 hydrolyzes BMP
General
Type : Phospholipid, Phosphatidylglycerol, Acyl-Glycerol, 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, [(2S)-2-hydroxy-3-[hydroxy-[(2S)-2-hydroxy-3-[(Z)-octadec-9-enoyl]oxypropoxy]phosphoryl]oxypropyl] (Z)-octadec-9-enoate
Canonical SMILES : O([P](=O)(O)OCC(CO)OC(CCCCCCCC=CCCCCCCCC)=O)CC(COC(=O)CCCCCCCC=CCCCCCCCC)O || CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)OCC(COC(=O)CCCCCCCC=CCCCCCCCC)O)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 || InChI=1S\/C42H79O10P\/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-35-39(43)37-51-53(47,48)52-38-40(44)36-50-42(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 || GNCZTBXGLUHKAP-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 || 857135 || CHEBI:139539 || (S,S) 18:1(9Z) BMP || (S,S)-bis-(3-oleoylglycero)-1-phosphate || (S,S)-bis-(3-oleoyl-sn-glycero)-1-phosphate || (S,S)-bis-[3-(9Z-octadecenoyl)glycero]-1-phosphate || 18:1 BMP (S,S) || sn-(3-oleoyl-2-hydroxy)-glycerol-1-phospho-sn-1'-(3'-oleoyl-2'-hydroxy)-glycerol || lysobisphosphatidic acid || LBPA || BMP 18:1_18:1
MW : 775.054 || 792.07
Formula : C42H79O10P
CAS_number : 1246303-12-7
UniChem : BLPKWNZZIJINCN-UHFFFAOYSA-N, ZCXRIDHJRROVJY-JOZUOZHYSA-N, GNCZTBXGLUHKAP-JOZUOZHYSA-N
phosphate.gif)
Target
Structures : No structure
Families : ABHD6-Lip, Lipoprotein_Lipase, Phospholipase, Hepatic_Lipase
References (7)
| Title : Lactylation Converts ABHD6 into a Mitochondrial Regulator that Drives Lenvatinib Resistance in Hepatocellular Carcinoma - Sun_2026_Cancer.Res__ |
| Author(s) : Sun Y , Luo C , Yang H , Ye J , Song F , Yi Q , Zou W , Huang Y , Fan X , Wang L , Zhang Y , Ding Q , Zhu Y , Tang Z |
| Ref : Cancer Research , : , 2026 |
| Abstract : |
| PubMedSearch : Sun_2026_Cancer.Res__ |
| PubMedID: 41861279 |
| 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 : Metabolic disease and ABHD6 alter the circulating bis(monoacylglycerol)phosphate profile in mice and humans - Grabner_2019_J.Lipid.Res_60_1020 |
| Author(s) : Grabner GF , Fawzy N , Pribasnig MA , Trieb M , Taschler U , Holzer M , Schweiger M , Wolinski H , Kolb D , Horvath A , Breinbauer R , Rulicke T , Rabl R , Lass A , Stadlbauer V , Hutter-Paier B , Stauber RE , Fickert P , Zechner R , Marsche G , Eichmann TO , Zimmermann R |
| Ref : J Lipid Res , 60 :1020 , 2019 |
| Abstract : |
| PubMedSearch : Grabner_2019_J.Lipid.Res_60_1020 |
| PubMedID: 30894461 |
| Gene_locus related to this paper: human-ABHD6 |
| Title : alpha\/beta Hydrolase Domain-containing 6 (ABHD6) Degrades the Late Endosomal\/Lysosomal Lipid Bis(monoacylglycero)phosphate - Pribasnig_2015_J.Biol.Chem_290_29869 |
| Author(s) : Pribasnig MA , Mrak I , Grabner GF , Taschler U , Knittelfelder O , Scherz B , Eichmann TO , Heier C , Grumet L , Kowaliuk J , Romauch M , Holler S , Anderl F , Wolinski H , Lass A , Breinbauer R , Marsche G , Brown JM , Zimmermann R |
| Ref : Journal of Biological Chemistry , 290 :29869 , 2015 |
| Abstract : |
| PubMedSearch : Pribasnig_2015_J.Biol.Chem_290_29869 |
| PubMedID: 26491015 |
| Gene_locus related to this paper: human-ABHD6 |
| Title : Biological function of the cellular lipid BMP-BMP as a key activator for cholesterol sorting and membrane digestion - Gallala_2011_Neurochem.Res_36_1594 |
| Author(s) : Gallala HD , Sandhoff K |
| Ref : Neurochem Res , 36 :1594 , 2011 |
| Abstract : |
| PubMedSearch : Gallala_2011_Neurochem.Res_36_1594 |
| PubMedID: 21136156 |
| 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 |
| Title : Role of LBPA and Alix in multivesicular liposome formation and endosome organization - Matsuo_2004_Science_303_531 |
| Author(s) : Matsuo H , Chevallier J , Mayran N , Le Blanc I , Ferguson C , Faure J , Blanc NS , Matile S , Dubochet J , Sadoul R , Parton RG , Vilbois F , Gruenberg J |
| Ref : Science , 303 :531 , 2004 |
| Abstract : |
| PubMedSearch : Matsuo_2004_Science_303_531 |
| PubMedID: 14739459 |