CL(i-12:0/a-17:0/i-17:0/i-17:0)[rac] (BioDeep_00000072454)
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C72H140O17P2 (1338.9565)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCC(C)CCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCC(C)C)COP(=O)(O)OCC(COP(=O)(O)OCC(COC(=O)CCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCCCCCC(C)C)O
InChI: InChI=1S/C72H140O17P2/c1-9-65(8)51-43-35-26-20-16-17-23-29-39-47-55-72(77)89-68(59-83-70(75)53-45-37-31-30-34-42-50-64(6)7)61-87-91(80,81)85-57-66(73)56-84-90(78,79)86-60-67(88-71(76)54-46-38-28-22-15-11-13-19-25-33-41-49-63(4)5)58-82-69(74)52-44-36-27-21-14-10-12-18-24-32-40-48-62(2)3/h62-68,73H,9-61H2,1-8H3,(H,78,79)(H,80,81)/t65?,66-,67-,68-/m1/s1
描述信息
CL(i-12:0/a-17:0/i-17:0/i-17:0)[rac] is a cardiolipin (CL). Cardiolipins are sometimes called double phospholipids because they have four fatty acid tails, instead of the usual two. They are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,3-diacylglyerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains. CL(i-12:0/a-17:0/i-17:0/i-17:0)[rac] contains one chain of 10-methylundecanoic acid at the C1 position, one chain of 14-methylhexadecanoic acid at the C2 position, two chains of 15-methylhexadecanoic acid at the C3 and C4 positions fatty acids. Cardiolipins are known to be present in all mammalian cells, especially cells with a high number of mitochondria. De novo synthesis of Cardiolipins begins with condensing phosphatidic acid (PA) with cytidine-5’-triphosphate (CTP) to form cytidine-diphosphate-1,2-diacyl-sn-glycerol (CDP-DG). Glycerol-3-phosphate is subsequently added to this newly formed CDP-DG molecule to form phosphatidylglycerol phosphate (PGP), which is immediately dephosphorylated to form PG. The final step is the process of condensing the PG molecule with another CDP-DG molecule to form a new cardiolipin, which is catalyzed by cardiolipin synthase. All new cardiolipins immediately undergo a series remodeling resulting in the common cardiolipin compositions. (PMID: 16442164). Cardiolipin synthase shows no selectivity for fatty acyl chains used in the de novo synthesis of cardiolipin (PMID: 16442164). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20\\% of the total lipid. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane and are important for mitochondrial respiratory capacity. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Tafazzin is an important enzyme in the remodeling of cardiolipins, and in contrast to cardiolipin synthase, it shows strong acyl specificity. This suggests that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipins and is the cause of Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164). BTHS patients seem to lack acyl specificity. As a result, there are many potential cardiolipin species that can exist (PMID: 16226238).
同义名列表
9 个代谢物同义名
[(2R)-3-({[(2R)-2,3-bis[(15-methylhexadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(14-methylhexadecanoyl)oxy]-3-[(10-methylundecanoyl)oxy]propoxy]phosphinic acid; (2R)-3-{[(2R)-2,3-bis[(15-methylhexadecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(14-methylhexadecanoyl)oxy]-3-[(10-methylundecanoyl)oxy]propoxy)phosphinic acid; 1-[1-isododecanoyl-2-anteisoheptadecanoyl-sn-glycero-3-phospho],3-[1,2-diisoheptadecanoyl-rac-glycero-3-phospho]-glycerol; Cardiolipin(i-12:0/a-17:0/i-17:0/i-17:0); CL(1-[i-12:0/a-17:0],3-[i-17:0/i-17:0]); CL(i-12:0/a-17:0/i-17:0/i-17:0)[rac]; CL(i-12:0/a-17:0/i-17:0/i-17:0); Cardiolipin(63:0); CL(63:0)
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
1 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(1)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/i-17:0/i-17:0):
Cytidine triphosphate + PA(i-12:0/a-17:0) ⟶ CDP-DG(i-12:0/a-17:0) + Pyrophosphate
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
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