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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2020-02-26 21:23:53 UTC
HMDB IDHMDB0002170
Secondary Accession Numbers
  • HMDB0006808
  • HMDB02170
  • HMDB06808
Metabolite Identification
Common NameMalonyl-CoA semialdehyde
DescriptionMalonyl-CoA semialdehyde is involved in the propanoate metabolism pathway. Malonyl-CoA semialdehyde can be reversibly produced from malonyl-CoA and 3-hydroxy-propionyl-CoA. Malonic semialdehyde is formed in the alternative pathway of propionate metabolism and in the catabolism of beta-alanine. Studies of these pathways in cultured cells from a patient with mitochondrial malonyl-CoA decarboxylase deficiency indicate that malonic semialdehyde is directly converted into acetyl-CoA in man. (PMID: 6418146 ).
Structure
Data?1582752233
Synonyms
ValueSource
1-Thiomalonaldehydic acid S-ester with coenzyme AHMDB
3-Oxopropionyl-CoAHMDB
3-Oxopropionyl-coenzyme AHMDB
Malonylsemialdehyde coenzyme AHMDB
Malonylsemialdehyde-CoAHMDB
Malonylsemialdehyde-coenzyme AHMDB
S-(3-OxopropanoateHMDB
S-(3-Oxopropanoate)CoAHMDB
S-(3-Oxopropanoate)coenzyme AHMDB
S-(3-Oxopropanoic acidHMDB
Chemical FormulaC24H38N7O18P3S
Average Molecular Weight837.581
Monoisotopic Molecular Weight837.120687673
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number6244-93-5
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
InChI Identifier
InChI=1S/C24H38N7O18P3S/c1-24(2,19(36)22(37)27-5-3-14(33)26-6-8-53-15(34)4-7-32)10-46-52(43,44)49-51(41,42)45-9-13-18(48-50(38,39)40)17(35)23(47-13)31-12-30-16-20(25)28-11-29-21(16)31/h7,11-13,17-19,23,35-36H,3-6,8-10H2,1-2H3,(H,26,33)(H,27,37)(H,41,42)(H,43,44)(H2,25,28,29)(H2,38,39,40)/t13-,17-,18-,19?,23-/m1/s1
InChI KeyNMEYBPUHJHMRHU-UXYNFSPESA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Alkyl phosphate
  • Phosphoric acid ester
  • 1,3-dicarbonyl compound
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Alpha-hydrogen aldehyde
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organic oxide
  • Organosulfur compound
  • Aldehyde
  • Carbonyl group
  • Primary amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.96 g/LALOGPS
logP-0.34ALOGPS
logP-7.2ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity177.63 m³·mol⁻¹ChemAxon
Polarizability72.58 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2901000120-d8b8cf23d71e39eff078Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913000000-85f9d77a21c262ea2740Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1911000000-d5f5ccef72ec24e66957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-015i-8930140460-d2ae2d624ce327523728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5910210010-c0645baef41add2c37e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-2ae98a1c88a11c397df3Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • Brain
  • Heart
  • Liver
  • Skeletal Muscle
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022882
KNApSAcK IDNot Available
Chemspider ID389702
KEGG Compound IDC05989
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6523
PubChem Compound440865
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brown GK, Scholem RD, Bankier A, Danks DM: Malonyl coenzyme A decarboxylase deficiency. J Inherit Metab Dis. 1984;7(1):21-6. [PubMed:6145813 ]
  2. Scholem RD, Brown GK: Metabolism of malonic semialdehyde in man. Biochem J. 1983 Oct 15;216(1):81-5. [PubMed:6418146 ]