Malonyl-CoA

Identification

Name
Malonyl-CoA
Accession Number
DB04524  (EXPT02180)
Type
Small Molecule
Groups
Experimental
Description

A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.

Structure
Thumb
Synonyms
  • Coenzyme A, S-(hydrogen propanedioate)
  • Malonyl coenzyme A
  • S-(Hydrogen malonyl)coenzyme A
Categories
UNII
Not Available
CAS number
524-14-1
Weight
Average: 853.58
Monoisotopic: 853.115602295
Chemical Formula
C24H38N7O19P3S
InChI Key
LTYOQGRJFJAKNA-DVVLENMVSA-N
InChI
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)/t12-,17-,18-,19+,23-/m1/s1
IUPAC Name
3-[(2-{3-[(2R)-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
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-oxoacyl-[acyl-carrier-protein] synthase 3Not AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)Disease
Malonyl-CoA Decarboxylase DeficiencyDisease
Biosynthesis of Unsaturated Fatty Acids (Stearoyl-CoA)Metabolic
Fatty Acid BiosynthesisMetabolic
Palmitate Biosynthesis Metabolic
Fatty Acid Elongation (Saturated)Metabolic
Palmitate Biosynthesis 2Metabolic
Flavonoid Biosynthesis (Dihydroflavonol Biosynthesis)Metabolic
Pyruvate MetabolismMetabolic
Pyruvate Kinase DeficiencyDisease
Biosynthesis of Unsaturated Fatty AcidsMetabolic
Biosynthesis of Unsaturated Fatty Acids (Tetracosanoyl-CoA)Metabolic
Fatty Acid BiosynthesisMetabolic
Propanoate MetabolismMetabolic
Leigh SyndromeDisease
Malonic AciduriaDisease
Biotin-Carboxyl Carrier Protein AssemblyMetabolic
Pyruvate MetabolismMetabolic
Pyruvate MetabolismMetabolic
Methylmalonic Aciduria Due to Cobalamin-Related DisordersDisease
Pyruvate Dehydrogenase Complex DeficiencyDisease
Primary Hyperoxaluria II, PH2Disease
Fatty Acid BiosynthesisMetabolic
Biosynthesis of Unsaturated Fatty Acids (Docosanoyl-CoA)Metabolic
Biosynthesis of Unsaturated Fatty Acids (Icosanoyl-CoA)Metabolic
Fatty Acid Biosynthesis Metabolic
Flavanone BiosynthesisMetabolic
Phenolic Malonylglucosides BiosynthesisMetabolic
Propanoate MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C00083
PubChem Compound
644066
PubChem Substance
46506952
ChemSpider
559121
ChEBI
15531
HET
MLC
Wikipedia
Malonyl-CoA
PDB Entries
1cml / 1hnj / 2e1t / 2f3x / 2q78 / 2xiq / 2xr7 / 3nyr / 4a0z / 5ab7
show 2 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.8 mg/mLALOGPS
logP-0.62ALOGPS
logP-7.1ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity178.55 m3·mol-1ChemAxon
Polarizability74.68 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5354
Blood Brain Barrier-0.8702
Caco-2 permeable-0.7258
P-glycoprotein substrateSubstrate0.7289
P-glycoprotein inhibitor INon-inhibitor0.7344
P-glycoprotein inhibitor IINon-inhibitor0.9939
Renal organic cation transporterNon-inhibitor0.9638
CYP450 2C9 substrateNon-substrate0.7799
CYP450 2D6 substrateNon-substrate0.7987
CYP450 3A4 substrateSubstrate0.5592
CYP450 1A2 substrateNon-inhibitor0.8091
CYP450 2C9 inhibitorNon-inhibitor0.7975
CYP450 2D6 inhibitorNon-inhibitor0.8382
CYP450 2C19 inhibitorNon-inhibitor0.7706
CYP450 3A4 inhibitorNon-inhibitor0.7851
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8953
Ames testNon AMES toxic0.6473
CarcinogenicityNon-carcinogens0.8502
BiodegradationNot ready biodegradable0.9867
Rat acute toxicity2.6856 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9742
hERG inhibition (predictor II)Non-inhibitor0.6159
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1912000130-da8095652669b99c8349
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0913000000-c93bc8aa729d6712ed08
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2911000000-dee360a0ee5e683d782c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9830140570-8e78a24b9858f67c1579
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-5910010010-97fdf25aafbfdff7c908
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-057i-6900100000-33483ed329c67d3c4cac

Taxonomy

Description
This compound 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
Coenzyme A and derivatives / Purine ribonucleoside diphosphates / Pentose phosphates / Ribonucleoside 3'-phosphates / Beta amino acids and derivatives / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Organic pyrophosphates / Aminopyrimidines and derivatives
show 21 more
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
show 50 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
malonyl-CoAs (CHEBI:15531)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Beta-ketoacyl-acyl-carrier-protein synthase iii activity
Specific Function
Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Catalyzes the first condensation reaction which initiates fatty acid...
Gene Name
fabH
Uniprot ID
P0A6R0
Uniprot Name
3-oxoacyl-[acyl-carrier-protein] synthase 3
Molecular Weight
33514.78 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:59