Record Information
Version3.6
Creation Date2006-08-12 20:30:43 UTC
Update Date2013-05-29 19:38:15 UTC
HMDB IDHMDB03419
Secondary Accession Numbers
  • HMDB06490
Metabolite Identification
Common NameFormyl-CoA
DescriptionFormyl-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 , 9166898 ).
Structure
Thumb
Synonyms
  1. Formyl coenzyme A
Chemical FormulaC22H36N7O17P3S
Average Molecular Weight795.544
Monoisotopic Molecular Weight795.110122987
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 Number13131-49-2
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 KeySXMOKYXNAPLNCW-BWGWEBPHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine 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 ParentCoenzyme A and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Lipid biosynthesis, Fatty acid transport
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.783Not Available
Predicted Properties
PropertyValueSource
water solubility4.47 g/LALOGPS
logP-0.65ALOGPS
logP-7ChemAxon
logS-2.2ALOGPS
pKa (strongest acidic)0.83ChemAxon
pKa (strongest basic)4.95ChemAxon
physiological charge-4ChemAxon
hydrogen acceptor count17ChemAxon
hydrogen donor count9ChemAxon
polar surface area363.63ChemAxon
rotatable bond count20ChemAxon
refractivity167.72ChemAxon
polarizability68.93ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Phytanic Acid Peroxisomal OxidationSMP00450Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023169
KNApSAcK IDNot Available
Chemspider ID388444
KEGG Compound IDC00798
BioCyc IDFORMYL-COA
BiGG ID36030
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03419
Metagene LinkHMDB03419
METLIN IDNot Available
PubChem Compound439313
PDB IDNot Available
ChEBI ID15522
References
Synthesis Referenceonsson, 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
  1. Croes K, Casteels M, Asselberghs S, Herdewijn P, Mannaerts GP, Van Veldhoven PP: Formation of a 2-methyl-branched fatty aldehyde during peroxisomal alpha-oxidation. FEBS Lett. 1997 Aug 4;412(3):643-5. Pubmed: 9276483
  2. Croes K, Van Veldhoven PP, Mannaerts GP, Casteels M: Production of formyl-CoA during peroxisomal alpha-oxidation of 3-methyl-branched fatty acids. FEBS Lett. 1997 Apr 28;407(2):197-200. Pubmed: 9166898

Enzymes

Gene Name:
UROD
Uniprot ID:
P06132
Gene Name:
UROS
Uniprot ID:
P10746
Gene Name:
HMBS
Uniprot ID:
P08397
Gene Name:
BLVRA
Uniprot ID:
P53004
Gene Name:
PPOX
Uniprot ID:
P50336
Gene Name:
FECH
Uniprot ID:
P22830
Gene Name:
HACL1
Uniprot ID:
Q9UJ83
Reactions
2-Hydroxyphytanoyl-CoA unknown Pristanal + Formyl-CoAdetails
Gene Name:
Not Available
Uniprot ID:
Q53FU1
Gene Name:
Not Available
Uniprot ID:
Q5TZY0
Gene Name:
DKFZp686P18130
Uniprot ID:
Q7KZA3