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Human Metabolome Database Version 3.5

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Showing metabocard for Formyl-CoA (HMDB03419)

Record Information
Version 3.5
Creation Date 2006-08-12 14:30:43 -0600
Update Date 2013-02-08 17:12:33 -0700
HMDB ID HMDB03419
Secondary Accession Numbers
  • HMDB06490
Metabolite Identification
Common Name Formyl-CoA
Description Formyl-CoA is formed during the alpha-oxidation process in liver peroxisomes, as a result of the alpha-oxidation of 3-methyl-substituted fatty acids. The amount of formyl-CoA formed constitutes 2 - 5% of the total formate. The formyl-CoA formed is not due to activation of formate - until now presumed to be the primary end-product of alpha-oxidation - but is rather than formate the end-product of alpha-oxidation. The cleavage of 2-hydroxy-3-methylhexadecanoyl-CoA to 2-methylpentadecanal and formate (formyl-CoA) is probably due to the presence of a specific lyase. (PMID: 9276483 Link_out, 9166898 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Formyl coenzyme A
Chemical Formula C22H36N7O17P3S
Average Molecular Weight 795.544
Monoisotopic Molecular Weight 795.110122987
IUPAC Name {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(formylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(formylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number 13131-49-2
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
InChI Identifier InChI=1S/C22H36N7O17P3S/c1-22(2,17(33)20(34)25-4-3-13(31)24-5-6-50-11-30)8-43-49(40,41)46-48(38,39)42-7-12-16(45-47(35,36)37)15(32)21(44-12)29-10-28-14-18(23)26-9-27-19(14)29/h9-12,15-17,21,32-33H,3-8H2,1-2H3,(H,24,31)(H,25,34)(H,38,39)(H,40,41)(H2,23,26,27)(H2,35,36,37)/t12-,15-,16-,17?,21-/m1/s1
InChI Key SXMOKYXNAPLNCW-BWGWEBPHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent Coenzyme A and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Lipid biosynthesis, Fatty acid transport
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -3.783 Not Available
Predicted Properties
Property Value Source
Water Solubility 4.47 g/L ALOGPS
LogP -0.65 ALOGPS
LogP -7 ChemAxon
LogS -2.25 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 17 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 363.63 A2 ChemAxon
Rotatable Bond Count 20 ChemAxon
Refractivity 167.72 ChemAxon
Polarizability 68.93 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Phytanic Acid Peroxisomal Oxidation SMP00450 Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023169
KNApSAcK ID Not Available
Chemspider ID 388444 Link_out
KEGG Compound ID C00798 Link_out
BioCyc ID FORMYL-COA Link_out
BiGG ID 36030 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB03419 Link_out
Metagene Link HMDB03419 Link_out
METLIN ID Not Available
PubChem Compound 439313 Link_out
PDB ID Not Available
ChEBI ID 15522 Link_out
References
Synthesis Reference onsson, Stefan; Ricagno, Stefano; Lindqvist, Ylva; Richards, Nigel G. J. Kinetic and mechanistic characterization of the formyl-CoA transferase from Oxalobacter formigenes. Journal of Biological Chemistry (2004), 279(34), 36003-36012.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: 5-aminolevulinate synthase, erythroid-specific, mitochondrial
Reactions:
  • succinyl-CoA + glycine = 5-aminolevulinate + CoA + CO2 [RN:R00830]
Gene Name: ALAS2
Uniprot ID: P22557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-aminolevulinate synthase, nonspecific, mitochondrial
Reactions:
  • succinyl-CoA + glycine = 5-aminolevulinate + CoA + CO2 [RN:R00830]
Gene Name: ALAS1
Uniprot ID: P13196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uroporphyrinogen decarboxylase
Reactions:
  • uroporphyrinogen III = coproporphyrinogen III + 4 CO2 [RN:R03197]
Gene Name: UROD
Uniprot ID: P06132 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Coproporphyrinogen-III oxidase, mitochondrial
Reactions:
  • coproporphyrinogen III + O2 + 2 H+ = protoporphyrinogen-IX + 2 CO2 + 2 H2O [RN:R03220]
Gene Name: CPOX
Uniprot ID: P36551 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uroporphyrinogen-III synthase
Reactions:
  • hydroxymethylbilane = uroporphyrinogen III + H2O [RN:R03165]
Gene Name: UROS
Uniprot ID: P10746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Porphobilinogen deaminase
Reactions:
  • 4 porphobilinogen + H2O = hydroxymethylbilane + 4 NH3 [RN:R00084]
Gene Name: HMBS
Uniprot ID: P08397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Biliverdin reductase A
Reactions:
  • bilirubin + NAD(P)+ = biliverdin + NAD(P)H + H+ [RN:R02391 R02393]
Gene Name: BLVRA
Uniprot ID: P53004 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protoporphyrinogen oxidase
Reactions:
  • protoporphyrinogen IX + 3 O2 = protoporphyrin IX + 3 H2O2 [RN:R03222]
Gene Name: PPOX
Uniprot ID: P50336 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ferrochelatase, mitochondrial
Reactions:
  • protoheme + 2 H+ = protoporphyrin + Fe2+ [RN:R00310]
Gene Name: FECH
Uniprot ID: P22830 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Delta-aminolevulinic acid dehydratase
Reactions:
  • 2 5-aminolevulinate = porphobilinogen + 2 H2O [RN:R00036]
Gene Name: ALAD
Uniprot ID: P13716 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome c oxidase assembly protein COX15 homolog
Reactions:
    Gene Name: COX15
    Uniprot ID: Q7KZN9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 2-hydroxyacyl-CoA lyase 1
    Reactions:
      Gene Name: HACL1
      Uniprot ID: Q9UJ83 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ferrochelatase
      Reactions:
      • protoheme + 2 H+ = protoporphyrin + Fe2+ [RN:R00310]
      Gene Name: Not Available
      Uniprot ID: Q53FU1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ferrochelatase
      Reactions:
      • protoheme + 2 H+ = protoporphyrin + Fe2+ [RN:R00310]
      Gene Name: Not Available
      Uniprot ID: Q5TZY0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ferrochelatase
      Reactions:
      • protoheme + 2 H+ = protoporphyrin + Fe2+ [RN:R00310]
      Gene Name: DKFZp686P18130
      Uniprot ID: Q7KZA3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA