Common NameMalonyl-coa
DescriptionMalonyl-CoA belongs to the class of organic compounds known as acyl-CoAs. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, malonyl-CoA is considered to be a fatty ester lipid molecule. Malonyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, malonyl-CoA participates in a number of enzymatic reactions. In particular, malonyl-CoA can be biosynthesized from acetyl-CoA; which is mediated by the enzyme acetyl-CoA carboxylase 1. In addition, malonyl-CoA can be converted into malonic acid and coenzyme A; which is catalyzed by the enzyme fatty acid synthase. Outside of the human body, malonyl-CoA has been detected, but not quantified in, several different foods, such as rapes, mamey sapotes, jew's ears, pepper (C. chinense), and Alaska wild rhubarbs. This could make malonyl-CoA a potential biomarker for the consumption of these foods. Malonyl-CoA is a coenzyme A derivative that plays a key role in fatty acid synthesis in the cytoplasmic and microsomal systems.
Structure
Molecular FormulaC24H38N7O19P3S
Average Mass853.58000
Monoisotopic Mass853.11560
IUPAC Name3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-oxopropanoic acid
Traditional Name3-({2-[3-(3-{[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-3-oxopropanoic acid
CAS Registry Number524-14-1
SMILESCC(C)(COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)([O-])[O-])[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)[O-]
InChI IdentifierInChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19+,23-/m1/s1
InChI KeyLTYOQGRJFJAKNA-DVVLENMVSA-N
CHEBI IDCHEBI:57384
HMDB IDHMDB0001175
Pathways
NameSMPDB/PathBank
Pyruvate metabolism
Propanoate metabolism
Leigh Syndrome
Malonic Aciduria
Methylmalonic Aciduria Due to Cobalamin-Related Disorders
Pyruvate Dehydrogenase Complex Deficiency
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Fatty Acid Biosynthesis
Malonyl-coa decarboxylase deficiency
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
StateSolid
Water Solubility3.80e+00 g/l
logP-0.62
logS-2.35
pKa (Strongest Acidic)0.82
pKa (Strongest Basic)4.97
Hydrogen Acceptor Count19
Hydrogen Donor Count10
Polar Surface Area400.93 Ų
Rotatable Bond Count22
Physiological Charge-5
Formal Charge0
Refractivity178.55 m³·mol⁻¹
Polarizability74.29

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