Record Information |
---|
Version | 5.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2023-02-21 17:15:24 UTC |
---|
HMDB ID | HMDB0001015 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | N-Formyl-L-methionine |
---|
Description | N-formyl-L-methionine is a L-methionine derivative in which one of the hydrogens attached to the nitrogen is replaced by a formyl group. It has a role as a metabolite. It is a proteinogenic amino acid, a N-formyl amino acid and a L-methionine derivative. It is a conjugate acid of a N-formyl-L-methioninate. N-Formyl-L-methionine belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Formyl-L-methionine is effective in the initiation of protein synthesis. The initiating methionine residue enters the ribosome as N-formylmethionyl-tRNA. This process occurs in Escherichia coli and other bacteria as well as in the mitochondria of eukaryotic cells. |
---|
Structure | InChI=1S/C6H11NO3S/c1-11-3-2-5(6(9)10)7-4-8/h4-5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1 |
---|
Synonyms | Value | Source |
---|
(2S)-2-(Formylamino)-4-(methylthio)butanoic acid | ChEBI | Formyl-methionine | ChEBI | N-Formylmethionine | ChEBI | (2S)-2-(Formylamino)-4-(methylthio)butanoate | Generator | Formylmethionine, N | HMDB | N Formylmethionine | HMDB | N-Formyl-L-methionine | KEGG |
|
---|
Chemical Formula | C6H11NO3S |
---|
Average Molecular Weight | 177.221 |
---|
Monoisotopic Molecular Weight | 177.045963913 |
---|
IUPAC Name | (2S)-2-formamido-4-(methylsulfanyl)butanoic acid |
---|
Traditional Name | N-formylmethionine |
---|
CAS Registry Number | 4289-98-9 |
---|
SMILES | CSCC[C@H](NC=O)C(O)=O |
---|
InChI Identifier | InChI=1S/C6H11NO3S/c1-11-3-2-5(6(9)10)7-4-8/h4-5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1 |
---|
InChI Key | PYUSHNKNPOHWEZ-YFKPBYRVSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | Methionine and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Methionine or derivatives
- N-acyl-l-alpha-amino acid
- N-formyl-alpha-amino acid
- N-formyl-alpha amino acid or derivatives
- Thia fatty acid
- Fatty acid
- Fatty acyl
- Carboxamide group
- Secondary carboxylic acid amide
- Dialkylthioether
- Sulfenyl compound
- Thioether
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Hydrocarbon derivative
- Organic oxide
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Experimental Collision Cross SectionsAdduct Type | Data Source | CCS Value (Å2) | Reference |
---|
[M-H]- | Baker | 140.733 | 30932474 |
|
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
N-Formyl-L-methionine,1TMS,isomer #1 | CSCC[C@H](NC=O)C(=O)O[Si](C)(C)C | 1608.4 | Semi standard non polar | 33892256 | N-Formyl-L-methionine,1TMS,isomer #2 | CSCC[C@@H](C(=O)O)N(C=O)[Si](C)(C)C | 1636.8 | Semi standard non polar | 33892256 | N-Formyl-L-methionine,2TMS,isomer #1 | CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C=O)[Si](C)(C)C | 1674.2 | Semi standard non polar | 33892256 | N-Formyl-L-methionine,2TMS,isomer #1 | CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C=O)[Si](C)(C)C | 1641.9 | Standard non polar | 33892256 | N-Formyl-L-methionine,2TMS,isomer #1 | CSCC[C@@H](C(=O)O[Si](C)(C)C)N(C=O)[Si](C)(C)C | 2015.8 | Standard polar | 33892256 | N-Formyl-L-methionine,1TBDMS,isomer #1 | CSCC[C@H](NC=O)C(=O)O[Si](C)(C)C(C)(C)C | 1834.8 | Semi standard non polar | 33892256 | N-Formyl-L-methionine,1TBDMS,isomer #2 | CSCC[C@@H](C(=O)O)N(C=O)[Si](C)(C)C(C)(C)C | 1861.6 | Semi standard non polar | 33892256 | N-Formyl-L-methionine,2TBDMS,isomer #1 | CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C=O)[Si](C)(C)C(C)(C)C | 2126.2 | Semi standard non polar | 33892256 | N-Formyl-L-methionine,2TBDMS,isomer #1 | CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C=O)[Si](C)(C)C(C)(C)C | 2088.6 | Standard non polar | 33892256 | N-Formyl-L-methionine,2TBDMS,isomer #1 | CSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C=O)[Si](C)(C)C(C)(C)C | 2219.0 | Standard polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental GC-MS | GC-MS Spectrum - N-Formyl-L-methionine GC-MS (2 TMS) | splash10-0pdi-1920000000-7ead52d367d0c14c2f83 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - N-Formyl-L-methionine GC-MS (1 TMS) | splash10-002r-9800000000-d6bd1c4a45710fcff139 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - N-Formyl-L-methionine EI-B (Non-derivatized) | splash10-004i-1900000000-dbd5e7526844833f2769 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - N-Formyl-L-methionine EI-B (Non-derivatized) | splash10-002b-1931000000-f6d54f9e00989580bf16 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - N-Formyl-L-methionine GC-EI-TOF (Non-derivatized) | splash10-0zi1-0920000000-eff4a723ccd21264f857 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - N-Formyl-L-methionine GC-EI-TOF (Non-derivatized) | splash10-002r-6900000000-f44202a7297064bce497 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - N-Formyl-L-methionine GC-EI-TOF (Non-derivatized) | splash10-0pdj-0920000000-4d46bd9a6a5f645fdee9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - N-Formyl-L-methionine GC-EI-TOF (Non-derivatized) | splash10-00di-9410000000-0d6268555c7a6ebf60ef | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Formyl-L-methionine GC-MS (Non-derivatized) - 70eV, Positive | splash10-000y-9200000000-10205de54a16e96cf3ad | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Formyl-L-methionine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , negative-QTOF | splash10-004i-0900000000-a5b03aa018c68be71432 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , negative-QTOF | splash10-002b-9600000000-e2a1a85ea82026c67c40 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , negative-QTOF | splash10-0002-9000000000-4f909deb0784221401df | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , negative-QTOF | splash10-0002-9000000000-e07240ba0c7d6b253cf3 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , negative-QTOF | splash10-0002-9000000000-04ba3fa1d5a4d4da730a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QTOF , negative-QTOF | splash10-004i-4900000000-b9244ecfa5c3afeec4c8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , positive-QTOF | splash10-03fr-0900000000-6cef5cfd02af4e4f5603 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , positive-QTOF | splash10-0fc0-2900000000-ca29f2380d125436464f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , positive-QTOF | splash10-0gx0-9600000000-d8211d4ecddfb71549d2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , positive-QTOF | splash10-0bu0-9200000000-95443fc05ab3a30f1736 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine LC-ESI-QQ , positive-QTOF | splash10-03di-9100000000-61580bdacfbf4ccd3b72 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine 10V, Negative-QTOF | splash10-002b-9300000000-6b6656d410859495b7d6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine 35V, Negative-QTOF | splash10-0002-9000000000-36639998e841668381bf | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine 20V, Negative-QTOF | splash10-0002-9000000000-00ec72b1c1c573b951a4 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine 30V, Negative-QTOF | splash10-0002-9000000000-42e1592f1bbdcb4b4283 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine 40V, Negative-QTOF | splash10-0002-9000000000-c901d1fde297485a1211 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine 35V, Positive-QTOF | splash10-03e9-9200000000-66fcb11cb1ad675d36b6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine 40V, Positive-QTOF | splash10-03di-9000000000-becdef0ad11ee4b6c1a0 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Formyl-L-methionine 20V, Positive-QTOF | splash10-08gi-9000000000-0cb78961b18f92893c52 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Formyl-L-methionine 10V, Positive-QTOF | splash10-0032-0900000000-8f385306243b675f9f3a | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Formyl-L-methionine 20V, Positive-QTOF | splash10-0faj-4900000000-e575d78a4fb6796b499f | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Formyl-L-methionine 40V, Positive-QTOF | splash10-0ug0-9600000000-fb463674953dd37d24d3 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Formyl-L-methionine 10V, Negative-QTOF | splash10-004j-9800000000-c1e3c8cc0a2b6fb080c7 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Formyl-L-methionine 20V, Negative-QTOF | splash10-0002-9300000000-0ba777d8c80b1cda51d6 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Formyl-L-methionine 40V, Negative-QTOF | splash10-0005-9000000000-7b1e231a15535ddad645 | 2017-07-26 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
|
---|
Disease References | Colorectal cancer |
---|
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Prostate cancer |
---|
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
|
|
---|