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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 15:27:56 UTC
Update Date2020-02-26 21:25:05 UTC
HMDB IDHMDB0004259
Secondary Accession Numbers
  • HMDB04259
Metabolite Identification
Common NameAcetyl-N-formyl-5-methoxykynurenamine
DescriptionAcetyl-N-formyl-5-methoxykynurenamine (AFMK) results from the oxidative cleavage of the pyrrole ring during melatonin oxidation by myeloperoxidase (MPO), a superoxide anion (O)-dependent reaction. AFMK is also expected to be formed from oxidation catalyzed by the unspecific enzyme indoleamine-2,3-dioxygenase (IDO), found in a variety of cell types including monocyte/macrophage lineages. MPO- and IDO-catalyzed melatonin oxidation has the requirement of O in common, a species formed in large amounts in inflammatory conditions. The non-enzymatic formation of AFMK can also be expected by its direct reaction with highly reactive oxygen species, such as hydroxyl radical and singlet oxygen. Thus, we assume that AFMK is a product formed in a route of melatonin metabolism, especially active in inflammation. As AFMK is biologically more active on leukocytes than melatonin, the metabolizing of melatonin to AFMK at inflammatory sites possibly plays a role in immunomodulation. AFMK is found in the CSF of patients with meningitis, and in some samples at a remarkably high concentration. AFMK was also found in some patients to exceed the concentration of melatonin normally found in serum (PMID: 16150112 ).
Structure
Data?1582752305
Synonyms
ValueSource
N-Acetyl-N-formyl-5-methoxykynurenamineHMDB
AFMKHMDB
Formyl-N-acetyl-5-methoxykynurenamineHMDB
N-[3-(2-Formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamideHMDB
N1-Acetyl-N2-formyl-5-methoxykynurenineHMDB
NSC 688263HMDB
K1HMDB
Chemical FormulaC13H16N2O4
Average Molecular Weight264.2771
Monoisotopic Molecular Weight264.11100701
IUPAC NameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
Traditional NameN-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
CAS Registry Number52450-38-1
SMILES
COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1
InChI Identifier
InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16)
InChI KeyJYWNYMJKURVPFH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Methoxyaniline
  • Anilide
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • N-arylamide
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Acetamide
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.158Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP0.5ALOGPS
logP0.34ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.5 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity70.8 m³·mol⁻¹ChemAxon
Polarizability27.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.98731661259
DarkChem[M-H]-159.41531661259
DeepCCS[M+H]+162.72430932474
DeepCCS[M-H]-160.36630932474
DeepCCS[M-2H]-193.25230932474
DeepCCS[M+Na]+168.81830932474
AllCCS[M+H]+160.632859911
AllCCS[M+H-H2O]+157.132859911
AllCCS[M+NH4]+163.932859911
AllCCS[M+Na]+164.832859911
AllCCS[M-H]-161.932859911
AllCCS[M+Na-2H]-162.232859911
AllCCS[M+HCOO]-162.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetyl-N-formyl-5-methoxykynurenamineCOC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C13805.9Standard polar33892256
Acetyl-N-formyl-5-methoxykynurenamineCOC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C12604.3Standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamineCOC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C12528.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #1COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C12555.1Semi standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #1COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C12672.1Standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #1COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C13499.4Standard polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #2COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C12452.0Semi standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #2COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C12578.0Standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TMS,isomer #2COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCNC(C)=O)=C13240.7Standard polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TMS,isomer #1COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C12367.6Semi standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TMS,isomer #1COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C12728.6Standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TMS,isomer #1COC1=CC=C(N(C=O)[Si](C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C)=C12968.8Standard polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #1COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C12791.8Semi standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #1COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C12879.0Standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #1COC1=CC=C(NC=O)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C13489.6Standard polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #2COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C12722.3Semi standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #2COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C12763.2Standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,1TBDMS,isomer #2COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCNC(C)=O)=C13312.9Standard polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TBDMS,isomer #1COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C12870.1Semi standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TBDMS,isomer #1COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C13066.6Standard non polar33892256
Acetyl-N-formyl-5-methoxykynurenamine,2TBDMS,isomer #1COC1=CC=C(N(C=O)[Si](C)(C)C(C)(C)C)C(C(=O)CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=C13134.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-EI-TOF (Non-derivatized)splash10-001i-1790000000-08a018599da99d3251112017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-EI-TOF (Non-derivatized)splash10-004r-1941000000-1fd6a7b0aa4a93746dce2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-EI-TOF (Non-derivatized)splash10-001i-1790000000-08a018599da99d3251112018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-EI-TOF (Non-derivatized)splash10-004r-1941000000-1fd6a7b0aa4a93746dce2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kfy-8790000000-29b99509d4ad702e0c172017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 35V, Positive-QTOFsplash10-01ri-0900000000-befc2619a8b03b67929f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 35V, Negative-QTOFsplash10-0f79-1920000000-c1e957900fd03a5369422021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 10V, Positive-QTOFsplash10-01bl-0190000000-cc0a8bf1c63ec5bda44d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 20V, Positive-QTOFsplash10-05dl-2970000000-e59ea14239ec95d818892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 40V, Positive-QTOFsplash10-0fbc-4900000000-87c88186c3d6cd7b6c512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 10V, Negative-QTOFsplash10-03dr-0090000000-6ea3042b8fae674f87bb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 20V, Negative-QTOFsplash10-00ku-3490000000-f9119264a2c3c84527652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 40V, Negative-QTOFsplash10-052f-9110000000-7e684511197690c0f5cb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 10V, Negative-QTOFsplash10-03di-1190000000-9ea054e52d4b2713e40a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 20V, Negative-QTOFsplash10-0a4l-9420000000-5c7a32c26de619ab85442021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 40V, Negative-QTOFsplash10-0006-9410000000-be01b9cb02bd8503009a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 10V, Positive-QTOFsplash10-0170-0490000000-010747a672f5eb1374f02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 20V, Positive-QTOFsplash10-05bg-1950000000-b11b95cdcd40b6ee721a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-N-formyl-5-methoxykynurenamine 40V, Positive-QTOFsplash10-0kou-2900000000-ab1aed32a73b1f6ab74e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000065 (0.000059-0.00189) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.28 (0.06-0.50) uMAdult (>18 years old)Not Specified
Meningitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIron deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Meningitis
  1. Silva SO, Ximenes VF, Livramento JA, Catalani LH, Campa A: High concentrations of the melatonin metabolite, N1-acetyl-N2-formyl-5-methoxykynuramine, in cerebrospinal fluid of patients with meningitis: a possible immunomodulatory mechanism. J Pineal Res. 2005 Oct;39(3):302-6. [PubMed:16150112 ]
Iron deficiency
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023355
KNApSAcK IDNot Available
Chemspider ID149637
KEGG Compound IDC05642
BioCyc IDNot Available
BiGG ID46183
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound171161
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDFNA5MOXAM
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis Referencede Almeida Eduardo A; Martinez Glaucia R; Klitzke Clecio F; de Medeiros Marisa H G; Di Mascio Paolo Oxidation of melatonin by singlet molecular oxygen (O2(1deltag)) produces N1-acetyl-N2-formyl-5-methoxykynurenine. Journal of pineal research (2003), 35(2), 131-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silva SO, Ximenes VF, Livramento JA, Catalani LH, Campa A: High concentrations of the melatonin metabolite, N1-acetyl-N2-formyl-5-methoxykynuramine, in cerebrospinal fluid of patients with meningitis: a possible immunomodulatory mechanism. J Pineal Res. 2005 Oct;39(3):302-6. [PubMed:16150112 ]

Enzymes

General function:
Involved in heme binding
Specific function:
Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:
IDO1
Uniprot ID:
P14902
Molecular weight:
45325.89
Reactions
Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenaminedetails
General function:
Involved in heme binding
Specific function:
Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
Gene Name:
IDO2
Uniprot ID:
Q6ZQW0
Molecular weight:
47074.745
Reactions
Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenaminedetails