Record Information
Version1.0
Created at2020-04-17 19:17:35 UTC
Updated at2020-11-18 16:39:29 UTC
CannabisDB IDCDB005182
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMalonyl-CoA
DescriptionMalonyl-CoA, also known as malonyl CoA or CoA, malonyl, belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group. Malonyl-CoA is a strong basic compound (based on its pKa). Within humans, malonyl-CoA participates in a number of enzymatic reactions. In particular, malonyl-CoA can be biosynthesized from acetyl-CoA through the action of 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. malonyl/acetyl transferase domain. Malonyl-CoA is a highly regulated molecule in fatty acid synthesis; as such, it inhibits the rate-limiting step in beta-oxidation of fatty acids. Malonyl-CoA inhibits fatty acids from associating with carnitine by regulating the enzyme carnitine acyltransferase, thereby preventing them from entering the mitochondria, where fatty acid oxidation and degradation occur. Malonyl-CoA is formed by carboxylating acetyl-CoA using the enzyme acetyl-CoA carboxylase. MCAT serves to transfer malonate from malonyl-CoA to the terminal thiol of holo-acyl carrier protein (ACP). In humans, malonyl-CoA is involved in fatty acid biosynthesis. In the former, it provides 2-carbon units to fatty acids and commits them to fatty acid chain synthesis. Malonyl-CoA is a potentially toxic compound. Malonyl-CoA is a coenzyme A derivative of malonic acid. MCAT is also involved in bacterial polyketide biosynthesis. The enzyme MCAT together with an acyl carrier protein (ACP), and a polyketide synthase (PKS) and chain-length factor heterodimer, constitutes the minimal PKS of type II polyketides. One molecule of acetyl-CoA joins with a molecule of bicarbonate, requiring energy rendered from ATP.Malonyl-CoA is utilised in fatty acid biosynthesis by the enzyme malonyl coenzyme A:acyl carrier protein transacylase (MCAT). It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis. Malonyl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
Malonyl CoAHMDB
Malonyl coenzyme AHMDB
Malonyl-coenzyme AHMDB
Omega-carboxyacyl-CoAHMDB
Omega-carboxyacyl-coenzyme AHMDB
S-(Hydrogen malonyl)coenzyme AHMDB
S-(Hydrogen propanedioateHMDB
S-(Hydrogen propanedioate) CoAHMDB
S-(Hydrogen propanedioate) coenzyme AHMDB
S-(Hydrogen propanedioic acidHMDB
a, Malonyl coenzymeHMDB
CoA, MalonylHMDB
coenzyme A, MalonylHMDB
Chemical FormulaC24H38N7O19P3S
Average Molecular Weight853.58
Monoisotopic Molecular Weight853.1156
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
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(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)/t12-,17-,18-,19?,23-/m1/s1
InChI KeyLTYOQGRJFJAKNA-VFLPNFFSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct Parent1,3-dicarbonyl compounds
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.5ALOGPS
logP-6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.2ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity178.55 m³·mol⁻¹ChemAxon
Polarizability74.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1931000120-97b61b6dd179da9fd5b32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0911000000-7f4a5a9af638e2913a5d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910000000-3b73db0d454b8cfd10a32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-8930142570-6dff4f741103c444a8bc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910110000-568b3152fb676f2c38e62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-7900100000-5557b31629ecb124d8ef2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001175
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001606
KNApSAcK IDC00007260
Chemspider ID10213
KEGG Compound IDC00083
BioCyc IDNot Available
BiGG ID33789
Wikipedia LinkMalonyl-CoA
METLIN ID6056
PubChem Compound10663
PDB IDNot Available
ChEBI ID15531
References
General ReferencesNot Available