| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2012-09-06 15:16:49 UTC |
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| Update Date | 2023-02-21 17:18:09 UTC |
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| HMDB ID | HMDB0014405 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Cycloserine |
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| Description | Cycloserine is only found in individuals that have used or taken this drug. It is an antibiotic substance produced by Streptomyces garyphalus. [PubChem]Cycloserine is an analog of the amino acid D-alanine. It interferes with an early step in bacterial cell wall synthesis in the cytoplasm by competitive inhibition of two enzymes, L-alanine racemase, which forms D-alanine from L-alanine, and D-alanylalanine synthetase, which incorporates D-alanine into the pentapeptide necessary for peptidoglycan formation and bacterial cell wall synthesis. |
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| Structure | InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1 |
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| Synonyms | | Value | Source |
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| (+)-4-Amino-3-isoxazolidinone | ChEBI | | (+)-Cycloserine | ChEBI | | (R)-4-AMINO-isoxazolidin-3-one | ChEBI | | alpha-Cycloserine | ChEBI | | Cicloserina | ChEBI | | Cyclo-D-serine | ChEBI | | Cycloserinum | ChEBI | | D-(+)-Cycloserine | ChEBI | | D-4-Amino-3-isoxazolidinone | ChEBI | | D-4-Amino-3-isoxazolidone | ChEBI | | DCS | ChEBI | | Orientomycin | ChEBI | | PA 94 | ChEBI | | PA-94 | ChEBI | | Ro-1-9213 | ChEBI | | Seromycin | ChEBI | | D-Cycloserine | Kegg | | ABBR DCS | Kegg | | a-Cycloserine | Generator | | Α-cycloserine | Generator | | D-CS | HMDB | | D-Cycloserine synth. BP 88 | HMDB | | D-Cycloserine, synthetic | HMDB | | D-Oxamicina | HMDB | | D-Oxamycin | HMDB | | DL-Cycloserine | HMDB | | L-Cycloserine | HMDB | | R-4-Amino-3-isoxazolidinone | HMDB |
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| Chemical Formula | C3H6N2O2 |
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| Average Molecular Weight | 102.0919 |
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| Monoisotopic Molecular Weight | 102.042927446 |
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| IUPAC Name | (4R)-4-amino-1,2-oxazolidin-3-one |
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| Traditional Name | cycloserine |
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| CAS Registry Number | 68-41-7 |
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| SMILES | [H][C@@]1(N)CON=C1O |
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| InChI Identifier | InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1 |
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| InChI Key | DYDCUQKUCUHJBH-UWTATZPHSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Azolines |
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| Sub Class | Isoxazolines |
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| Direct Parent | Isoxazolines |
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| Alternative Parents | |
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| Substituents | - Isoxazoline
- Oxacycle
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Amine
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Not Available |
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| Disposition | |
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| Process | Not Available |
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| Role | Not Available |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 0.63 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 8.5733 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 5.76 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 255.6 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 557.9 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 336.6 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 67.9 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 226.7 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 60.8 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 258.2 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 239.3 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 644.2 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 569.3 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 42.7 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 694.6 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 206.8 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 255.9 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 578.8 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 365.8 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 291.9 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Cycloserine,1TMS,isomer #1 | C[Si](C)(C)OC1=NOC[C@H]1N | 1287.6 | Semi standard non polar | 33892256 | | Cycloserine,1TMS,isomer #2 | C[Si](C)(C)N[C@@H]1CON=C1O | 1351.4 | Semi standard non polar | 33892256 | | Cycloserine,2TMS,isomer #1 | C[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C | 1434.8 | Semi standard non polar | 33892256 | | Cycloserine,2TMS,isomer #1 | C[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C | 1535.5 | Standard non polar | 33892256 | | Cycloserine,2TMS,isomer #1 | C[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C | 2443.8 | Standard polar | 33892256 | | Cycloserine,2TMS,isomer #2 | C[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C | 1455.5 | Semi standard non polar | 33892256 | | Cycloserine,2TMS,isomer #2 | C[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C | 1523.8 | Standard non polar | 33892256 | | Cycloserine,2TMS,isomer #2 | C[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C | 2303.8 | Standard polar | 33892256 | | Cycloserine,3TMS,isomer #1 | C[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C)[Si](C)(C)C | 1550.8 | Semi standard non polar | 33892256 | | Cycloserine,3TMS,isomer #1 | C[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C)[Si](C)(C)C | 1622.8 | Standard non polar | 33892256 | | Cycloserine,3TMS,isomer #1 | C[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C)[Si](C)(C)C | 2080.6 | Standard polar | 33892256 | | Cycloserine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=NOC[C@H]1N | 1497.3 | Semi standard non polar | 33892256 | | Cycloserine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@@H]1CON=C1O | 1560.4 | Semi standard non polar | 33892256 | | Cycloserine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C(C)(C)C | 1861.8 | Semi standard non polar | 33892256 | | Cycloserine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C(C)(C)C | 1895.5 | Standard non polar | 33892256 | | Cycloserine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C(C)(C)C | 2493.0 | Standard polar | 33892256 | | Cycloserine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C(C)(C)C | 1815.4 | Semi standard non polar | 33892256 | | Cycloserine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C(C)(C)C | 1986.7 | Standard non polar | 33892256 | | Cycloserine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C(C)(C)C | 2285.2 | Standard polar | 33892256 | | Cycloserine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2122.0 | Semi standard non polar | 33892256 | | Cycloserine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2185.4 | Standard non polar | 33892256 | | Cycloserine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2215.6 | Standard polar | 33892256 |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental GC-MS | GC-MS Spectrum - Cycloserine GC-MS (2 TMS) | splash10-0uy0-5900000000-06bce0b228f324fe49b4 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Cycloserine GC-MS (Non-derivatized) | splash10-0uy0-5900000000-06bce0b228f324fe49b4 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Cycloserine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-0e7a5a8b0f7ce48e4509 | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Cycloserine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 10V, Positive-QTOF | splash10-0udi-4900000000-f1c1692f9e6318f52377 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 20V, Positive-QTOF | splash10-0f79-9300000000-45585d9e68724372ca94 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 40V, Positive-QTOF | splash10-059f-9000000000-bac95a810bc34e20e690 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 10V, Negative-QTOF | splash10-0udi-5900000000-5babaf58090cc358ab6e | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 20V, Negative-QTOF | splash10-0f6x-9300000000-0ff851b2ef4ce71985ff | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 40V, Negative-QTOF | splash10-0596-9000000000-8a39f19e4a34080991d1 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 10V, Negative-QTOF | splash10-0udl-9800000000-28ac2fbbebd31cc6100b | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 20V, Negative-QTOF | splash10-0006-9200000000-739f88bc4c62ad6e99a6 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 40V, Negative-QTOF | splash10-0006-9000000000-90726b17dc36e29c5299 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 10V, Positive-QTOF | splash10-0udi-0900000000-940c87bcfe09a2af1fc9 | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 20V, Positive-QTOF | splash10-0w2c-9400000000-13b86532b272b0b5785d | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cycloserine 40V, Positive-QTOF | splash10-0006-9000000000-a3d694a542f40615fe9e | 2021-09-23 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
IR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| 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 |
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