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Showing Compound Malonyl-CoA semialdehyde (FDB022882)

Record Information
Version1.0
Creation date2011-09-21 00:21:03 UTC
Update date2015-07-21 06:57:24 UTC
Primary IDFDB022882
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number6244-93-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
Malonylsemialdehyde-Coenzyme Ahmdb
S-(3-oxopropanoatehmdb
S-(3-oxopropanoate)CoAhmdb
S-(3-oxopropanoate)Coenzyme Ahmdb
S-(3-oxopropanoic acidhmdb
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
Chemical FormulaC24H38N7O18P3S
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
InChI IdentifierInChI=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
Isomeric SMILESCC(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
Average Molecular Weight837.581
Monoisotopic Molecular Weight837.120687673
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2901000120-d8b8cf23d71e39eff0782017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913000000-85f9d77a21c262ea27402017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1911000000-d5f5ccef72ec24e669572017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-015i-8930140460-d2ae2d624ce3275237282017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5910210010-c0645baef41add2c37e72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-2ae98a1c88a11c397df32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0300000090-54c5c97b3cdaf7361c4b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000020-d7b327fea980a5ff314a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0119000000-6d29d610960646fde4e72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-8ae5fee026330ee5434d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-015m-7100002970-d15bc4d943bd653737662021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004s-7002405900-ae27dfa3dc95b82503692021-09-24View Spectrum
NMRNot Available
ChemSpider ID389702
ChEMBL IDNot Available
KEGG Compound IDC05989
Pubchem Compound ID440865
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02170
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Propanoate MetabolismSMP00016 map00640
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference