ChemFOnt: Showing chemical card for Malonyl-CoA (CFc000000911)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:26 UTC

Chemfont ID

CFc000000911

Molecule Identification

Common Name

Malonyl-CoA

Definition

Malonyl-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
coenzyme A, Malonyl	MeSH
Malonyl CoA	MeSH
a, Malonyl coenzyme	MeSH
CoA, Malonyl	MeSH

Chemical Formula

C₂₄H₃₈N₇O₁₉P₃S

Average Molecular Weight

853.58

Monoisotopic Molecular Weight

853.115602295

IUPAC Name

3-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-3-oxopropanoic acid

Traditional Name

3-[(2-{[3-({4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene}amino)-1-hydroxypropylidene]amino}ethyl)sulfanyl]-3-oxopropanoic acid

CAS Registry Number

524-14-1

SMILES

CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CC(O)=O

InChI Identifier

InChI=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)

InChI Key

LTYOQGRJFJAKNA-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
1,3-dicarbonyl compound
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Azole
Thiocarboxylic acid ester
Carbothioic s-ester
Secondary alcohol
Amino acid
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Azacycle
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organosulfur compound
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Adipose tissue (HMDB: HMDB0001175)

Muscle tissue

Skeletal muscle (HMDB: HMDB0001175)

Cell

Fibroblasts (HMDB: HMDB0001175)

Organ

Liver (HMDB: HMDB0001175)
Pancreas (HMDB: HMDB0001175)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001175)
Peroxisome (HMDB: HMDB0001175)

Extracellular (HMDB: HMDB0001175)
Membrane (HMDB: HMDB0001175)

Tissue substructure

Muscle (HMDB: HMDB0001175)

Source

Exogenous

Exogenous (HMDB: HMDB0001175)

Food

Cereal and cereal product

Cereal

Sorghum (FooDB: FOOD00177)

Endogenous

Endogenous (HMDB: HMDB0001175)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyruvate Metabolism (HMDB: HMDB0001175)
Fatty Acid Biosynthesis (HMDB: HMDB0001175)
Propanoate Metabolism (HMDB: HMDB0001175)
Fatty Acid Biosynthesis (PathBank: SMP0002360)
Fatty Acid Elongation (Saturated) (PathBank: SMP0121280)
Palmitate Biosynthesis 2 (PathBank: SMP0122231)
Biotin-Carboxyl Carrier Protein Assembly (PathBank: SMP0122242)
Palmitate Biosynthesis (PathBank: SMP0121279)
Biosynthesis of Unsaturated Fatty Acids (PathBank: SMP0002324)
Biosynthesis of Unsaturated Fatty Acids (Tetracosanoyl-CoA) (PathBank: SMP0002325)
Biosynthesis of Unsaturated Fatty Acids (Docosanoyl-CoA) (PathBank: SMP0002329)
Biosynthesis of Unsaturated Fatty Acids (Icosanoyl-CoA) (PathBank: SMP0002346)
Biosynthesis of Unsaturated Fatty Acids (Stearoyl-CoA) (PathBank: SMP0002347)
Flavonoid Biosynthesis (PathBank: SMP0012021)
Phenolic Malonylglucosides Biosynthesis (PathBank: SMP0012076)

Disease pathway

Malonic Aciduria (HMDB: HMDB0001175)
Leigh Syndrome (PathBank: SMP0120726)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (PathBank: SMP0120533)
Pyruvate Kinase Deficiency (PathBank: SMP0120623)
Methylmalonic Aciduria Due to Cobalamin-Related Disorders (PathBank: SMP0120748)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0120841)
Pyruvate Dehydrogenase Complex Deficiency (PathBank: SMP0120531)
Malonyl-CoA Decarboxylase Deficiency (PathBank: SMP0120786)

Protein pathway

LPS and Citrate Signaling and Inflammation (PathBank: SMP0120946)

Role

Biological role

Metabolite (HMDB: HMDB0001175)

Modulator

Inhibitor

EC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor (HMDB: HMDB0001175)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.66 g/L	ALOGPS
logP	-0.5	ALOGPS
logP	-4.4	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.29	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	407.91 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	179.6 m³·mol⁻¹	ChemAxon
Polarizability	73.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001606

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Malonyl-CoA

METLIN ID

Not Available

PubChem Compound

869

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Hulsmann, W. C. Synthesis of malonyl coenzyme A from acetyl coenzyme A and oxalosuccinate in mitochondria. Biochimica et Biophysica Acta (1963), 77(3), 502-3.

Showing chemical card for Malonyl-CoA (CFc000000911)

MOL for CFc000000911 (Malonyl-CoA)

3D MOL for CFc000000911 (Malonyl-CoA)

3D SDF for CFc000000911 (Malonyl-CoA)

3D-SDF for CFc000000911 (Malonyl-CoA)

PDB for CFc000000911 (Malonyl-CoA)

3D PDB for CFc000000911 (Malonyl-CoA)

SMILES for CFc000000911 (Malonyl-CoA)

INCHI for CFc000000911 (Malonyl-CoA)

Structure for CFc000000911 (Malonyl-CoA)

3D Structure for CFc000000911 (Malonyl-CoA)