Structure via PubChem · Public domain (PubChem)
methylmalonyl-CoA
Sign in to saveAlso known as Methylmalonyl coenzyme A
Methylmalonyl-CoA is the thioester consisting of coenzyme A linked to methylmalonic acid. It is an important intermediate in the biosynthesis of succinyl-CoA, which plays an essential role in the citric acid cycle.
Chemical data
- Formula
- C25H40N7O19P3S
- Molecular weight
- 867.6 g/mol
- IUPAC name
- 3-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethylsulfanyl]-2-methyl-3-oxopropanoic acid
- SMILES
- CC(C(=O)O)C(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O
- InChIKey
- MZFOKIKEPGUZEN-FBMOWMAESA-N
- XLogP
- -5.4
- Polar surface area
- 426 Ų
- H-bond donors
- 10
- H-bond acceptors
- 24
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 867.131253
Show 4 more facts
- chemical formula
- C₂₅H₄₀N₇O₁₉P₃S
- isomeric SMILES
- CC(C(=O)O)C(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)O
- canonical SMILES
- CC(C(=O)O)C(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)O
- found in taxon
- Homo sapiens
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Biosynthesis and metabolism
- Vitamin B<sub>12</sub>
- Related diseases
- Methylmalonic Acidemia (MMA)
- Combined malonic and methylmalonic aciduria (CMAMMA)
- References
Methylmalonyl-CoA is the thioester consisting of coenzyme A linked to methylmalonic acid. It is an important intermediate in the biosynthesis of succinyl-CoA, which plays an essential role in the citric acid cycle.
== Biosynthesis and metabolism == left|thumb|Propionate metabolic pathway with L- and D-methylmalonyl-CoA as intermediates. Methylmalonyl-CoA can be synthesized in two ways: From propionyl-CoA: Methylmalonyl-CoA results from the metabolism of fatty acid with an odd number of carbons, of amino acids valine, isoleucine, methionine, threonine or of cholesterol side-chains, forming Propionyl-CoA. The latter is also formed from propionic acid, which bacteria produce in the intestine. Propionyl-CoA and bicarbonate are converted to Methylmalonyl-CoA by the enzyme propionyl-CoA Carboxylase. It then is converted into succinyl-CoA by methylmalonyl-CoA mutase (MUT). This reaction is a reversible isomerization. In this way, the compound enters the citric acid cycle. The following diagram demonstrates the aforementioned reaction:
Excerpted from Wikipedia’s “methylmalonyl-CoA” article, available under the CC BY-SA 4.0 licence.