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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 20:30:43 UTC
Update Date2021-09-14 14:59:13 UTC
HMDB IDHMDB0003419
Secondary Accession Numbers
  • HMDB0006490
  • HMDB03419
  • 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
Data?1582752276
Synonyms
ValueSource
Formyl coenzyme AHMDB
Formyl-coenzyme AHMDB
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 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
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.783Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.47 g/LALOGPS
logP10(-0.65) g/LALOGPS
logP10(-7) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity167.72 m³·mol⁻¹ChemAxon
Polarizability68.93 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Formyl-CoACC(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=O5602.6Standard polar33892256
Formyl-CoACC(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=O4319.3Standard non polar33892256
Formyl-CoACC(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=O6258.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9243455200-7fe33bf6d4a771fe58062017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formyl-CoA GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 10V, Positive-QTOFsplash10-000i-1910000300-55d9e03540fe476863952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 20V, Positive-QTOFsplash10-000i-1930000000-f7d8ae48e314d038f7b22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 40V, Positive-QTOFsplash10-000i-2910000000-b160c588de2d041e4b802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 10V, Negative-QTOFsplash10-003r-5820231900-1838b37d7ea4f52f4b462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 20V, Negative-QTOFsplash10-003r-3910100100-933e5170643e8bcc224c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 40V, Negative-QTOFsplash10-057i-5900000000-7b6b8f24e737e82fc12e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 10V, Negative-QTOFsplash10-0006-0000000900-9964bca7fa7ce013e5112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 20V, Negative-QTOFsplash10-0032-2100003900-ec87a8b97c33e09176bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 40V, Negative-QTOFsplash10-002b-9002417200-07e062501318a903fb232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 10V, Positive-QTOFsplash10-0002-0300000900-581000df4cf64f4f53932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 20V, Positive-QTOFsplash10-000i-1910000200-eab4676c05a4b9c71eae2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formyl-CoA 40V, Positive-QTOFsplash10-000i-1490000000-0296bea622f0a9d9f65c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB023169
KNApSAcK IDNot Available
Chemspider ID388444
KEGG Compound IDC00798
BioCyc IDNot Available
BiGG ID36030
Wikipedia LinkAcyl-CoA
METLIN IDNot Available
PubChem Compound439313
PDB IDNot Available
ChEBI ID15522
Food Biomarker OntologyNot Available
VMH IDFORMCOA
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]

Only showing the first 10 proteins. There are 15 proteins in total.

Enzymes

General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS2
Uniprot ID:
P22557
Molecular weight:
64632.86
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS1
Uniprot ID:
P13196
Molecular weight:
70580.325
General function:
Involved in uroporphyrinogen decarboxylase activity
Specific function:
Catalyzes the decarboxylation of four acetate groups of uroporphyrinogen-III to yield coproporphyrinogen-III.
Gene Name:
UROD
Uniprot ID:
P06132
Molecular weight:
40786.58
General function:
Involved in coproporphyrinogen oxidase activity
Specific function:
Key enzyme in heme biosynthesis. Catalyzes the oxidative decarboxylation of propionic acid side chains of rings A and B of coproporphyrinogen III.
Gene Name:
CPOX
Uniprot ID:
P36551
Molecular weight:
50151.605
General function:
Involved in uroporphyrinogen-III synthase activity
Specific function:
Catalyzes cyclization of the linear tetrapyrrole, hydroxymethylbilane, to the macrocyclic uroporphyrinogen III, the branch point for the various sub-pathways leading to the wide diversity of porphyrins. Porphyrins act as cofactors for a multitude of enzymes that perform a variety of processes within the cell such as methionine synthesis (vitamin B12) or oxygen transport (heme).
Gene Name:
UROS
Uniprot ID:
P10746
Molecular weight:
28627.37
General function:
Involved in hydroxymethylbilane synthase activity
Specific function:
Tetrapolymerization of the monopyrrole PBG into the hydroxymethylbilane pre-uroporphyrinogen in several discrete steps.
Gene Name:
HMBS
Uniprot ID:
P08397
Molecular weight:
39329.74
General function:
Involved in biliverdin reductase activity
Specific function:
Reduces the gamma-methene bridge of the open tetrapyrrole, biliverdin IX alpha, to bilirubin with the concomitant oxidation of a NADH or NADPH cofactor.
Gene Name:
BLVRA
Uniprot ID:
P53004
Molecular weight:
33428.225
General function:
Involved in catalytic activity
Specific function:
Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX.
Gene Name:
PPOX
Uniprot ID:
P50336
Molecular weight:
50764.8
General function:
Involved in ferrochelatase activity
Specific function:
Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name:
FECH
Uniprot ID:
P22830
Molecular weight:
47861.77
General function:
Involved in porphobilinogen synthase activity
Specific function:
Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen.
Gene Name:
ALAD
Uniprot ID:
P13716
Molecular weight:
36294.485

Only showing the first 10 proteins. There are 15 proteins in total.