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Human Metabolome Database Version 2.5

 

Showing metabocard for Malonyl-CoA semialdehyde (HMDB02170)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 15:17:39
Update Date 2009-05-05 20:59:09
Accession Number HMDB02170
Secondary Accession Numbers HMDB06808
Common Name Malonyl-CoA semialdehyde
Description Malonyl-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)
Synonyms
  1. 1-Thiomalonaldehydic acid S-ester with coenzyme A
  2. Malonylsemialdehyde coenzyme A
  3. Malonylsemialdehyde-CoA
  4. S-(3-oxopropanoate)Coenzyme A
  5. Malonylsemialdehyde-Coenzyme A
  6. S-(3-oxopropanoate)CoA
  7. 3-Oxopropionyl-CoA
  8. 3-Oxopropionyl-coenzyme A
  9. S-(3-oxopropanoic acid
  10. S-(3-oxopropanoate
Chemical IUPAC Name S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-oxopropanethioate
Chemical Formula C24H38N7O18P3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Coenzyme A Derivatives
Sub Class
  • Short chain acyl CoAs
Family
  • Mammalian Metabolite
Species
  • aldehyde
  • secondary alcohol
  • primary amine
  • primary aromatic amine
  • secondary carboxylic acid amide
  • thiocarboxylic acid ester
  • phosphoric acid ester
  • aromatic compound
  • heterocyclic compound
Biofunction
  • Lipid biosynthesis, Fatty acid transport
Application
—
Source
  • Endogenous
Average Molecular Weight 837.581
Monoisotopic Molecular Weight 837.120667
Isomeric 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
Canonical SMILES CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CC=O
KEGG Compound ID C05989 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02170 Link Image
Metagene Link HMDB02170 Link Image
METLIN ID 6523 Link Image
PubChem Compound 440865 Link Image
PubChem Substance 50575214 Link Image
ChEBI ID Not Available
CAS Registry Number 6244-93-5
InChI Identifier InChI=1/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
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.96 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -4
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.34 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location
Tissue References
Brain —
Heart —
Liver —
Skeletal Muscle —
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Propanoate Metabolism SMP00016 Link Image map00640 Link Image
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 Link Image]
  2. Scholem RD, Brown GK: Metabolism of malonic semialdehyde in man. Biochem J. 1983 Oct 15;216(1):81-5. [PubMed Link Image]