Metabolite information |
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| HMDB ID | HMDB0013609 |
| Synonyms |
D-TryptophaneD-TrytophaneD-[+]-TryptophanD-alpha-amino-3-Indolepropionic acidDL-TryptophanDTRH-D-TRP-OHH-delta-TRP-OHTryptophan[+]-Tryptophan[2R]-2-amino-3-[1H-indol-3-yl]Propanoate[2R]-2-amino-3-[1H-indol-3-yl]Propanoic acid[R]-2-amino-3-[3-Indolyl]propionic acid[R]-Tryptophan[R]-[+]-2-amino-3-[3-Indolyl]propionic aciddelta-Tryptophanedelta-Trytophanedelta-[+]-Tryptophandelta-alpha-amino-3-Indolepropionic acid |
| Chemical formula | C11H12N2O2 |
| IUPAC name | (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid |
| CAS registry number | 153-94-6 |
| Monisotopic molecular weight | 204.089877638 |
Chemical taxonomy |
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| Super class | Organoheterocyclic compounds |
| Class | Indoles and derivatives |
| Sub class | Indolyl carboxylic acids and derivatives |
Biological properties |
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| Pahtways |
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| Author-emphasized biomarker in the paper(s) |
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| Reference | Country | Specimen | Marker function | Participants (Case) | Participants (Control) | |||||||||
| Cancer type | Stage | Number | Gender (M,F) | Age mean (range) (M/F) | Smoking status | Type | Number | Gender (M,F) | Age mean (range) (M/F) | Smoking status | ||||
| Sappington et al. 2018 | – | lymph node aspirates | diagnosis | adenocarcinoma | II, III, IV | 31 | 17, 14 | – | – | squamous cell carcinoma | 19 | 14, 5 | – | – |
| Fahrmann et al. 2015 | – | serum | diagnosis | adenocarcinoma | I, II, III, IV | 43 | 21, 22 | 67.3 ± 10.10 | – | healthy | 43 | 21, 22 | 65.9 ± 8.05 | – |
| Maeda et al. 2010 | – | plasma | – | NSCLC | I, II, III, IV | 141 | 93, 48 | 62.7 ± 9.2 | former, current, non-smoker | healthy | 423 | 279, 144 | 61.1 ± 8.7 | former, current, non-smoker |
| Fahrmann et al. 2015 | – | plasma | diagnosis | adenocarcinoma | I, II, III, IV | 43 | 21, 22 | 67.3 ± 10.10 | – | healthy | 43 | 21, 22 | 65.9 ± 8.05 | – |
| Miyamoto et al. 2015 | – | blood | diagnosis | NSCLC, SCLC, mesothelioma, secondary metastasis to lung | I, II, III, IV | 11 | 4, 7 | 67 (61-73) / 67 (47-76) | smoker, non-smoker | healthy | 11 | 5, 6 | 69 (61-83) / 54 (44-61) | unknown |
| Fahrmann et al. 2015 | – | serum | diagnosis | adenocarcinoma | I, II, III, IV | 49 | 17, 32 | 65.9 ± 9.87 | – | healthy | 31 | 11, 20 | 64.1 ± 8.97 | – |
| Klupczynska et al. 2016a | – | serum | diagnosis | adenocarcinoma, squamous cell carcinoma | I, II, III | 90 | 58, 32 | 64 (48-86) | current, non-smoker, unknown | healthy | 63 | 41, 22 | 62 (43-78) | smoker, non-smoker, unknown |
| An et al. 2010 | – | urine | diagnosis | adenocarcinoma, squamous cell carcinoma, SCLC | – | 19 | – | 61 ± 8.4 | – | healthy | 22 | – | – | – |
| Miyamoto et al. 2015 | – | blood | diagnosis | adenocarcinoma | unknown (mostly late stage) | 18 | 10, 8 | 67 (50-85) / 62 (53-72) | former, current | healthy | 20 | 8, 12 | 64 (49-80) / 66 (58-82) | former, current |
| Sappington et al. 2018 | – | lymph node aspirates | diagnosis | adenocarcinoma, squamous cell carcinoma | II, III, IV | 50 | 31, 19 | – | – | non-malignant | 29 | 15, 14 | – | – |
| Fahrmann et al. 2015 | – | plasma | diagnosis | adenocarcinoma | I, II, III, IV | 52 | 17, 35 | 65.9 ± 9.66 | – | healthy | 31 | 11, 20 | 64.1 ± 8.97 | – |
| Mazzone et al. 2016 | – | serum | – | adenocarcinoma, squamous cell carcinoma | I, II, III | 94 | 55.3%, 44.7% | 68.7 | – | at-risk controls | 190 | 50.5%, 49.5% | 66.2 | – |
| An et al. 2010 | – | urine | diagnosis | adenocarcinoma, squamous cell carcinoma, SCLC | – | 19 | – | 61 ± 8.4 | – | healthy | 22 | – | – | – |
| Moreno et al. 2018 | – | tissue | therapy, diagnosis | squamous cell carcinoma | I, II, III | 35 | 35, 0 | 68.71 ± 7.46 | – | tumor vs. adjacent normal tissue | 35 | 35, 0 | 68.71 ± 7.46 | – |
| Moreno et al. 2018 | – | tissue | therapy, diagnosis | adenocarcinoma | I, II, III | 33 | 24, 9 | 62.11 ± 9.73 | – | tumor vs. adjacent normal tissue | 33 | 24, 9 | 62.11 ± 9.73 | – |
| Wikoff et al. 2015b | – | tissue | diagnosis | adenocarcinoma | I | 39 | 15, 24 | 72.33 ± 8.78 | smoker, non-smoker | tumor vs. adjacent normal tissue | 39 | 15, 24 | 72.33 ± 8.78 | smoker, non-smoker |
| Reference | Chromatography | Ion source | Positive/Negative mode | Mass analyzer | Identification level |
| Sappington et al. 2018 | LC | ESI | positive | Q-TOF | MS/MS |
| Fahrmann et al. 2015 | GC | EI | – | TOF | – |
| Maeda et al. 2010 | LC | ESI | positive | quadrupole | – |
| Fahrmann et al. 2015 | GC | EI | – | TOF | – |
| Miyamoto et al. 2015 | GC | EI | – | TOF | MS/MS |
| Fahrmann et al. 2015 | GC | EI | – | TOF | – |
| Klupczynska et al. 2016a | LC | – | – | QTRAP | MS/MS |
| An et al. 2010 | LC | APCI | positive | Q-TOF | MS/MS |
| Miyamoto et al. 2015 | GC | EI | – | TOF | MS/MS |
| Sappington et al. 2018 | LC | ESI | positive | Q-TOF | MS/MS |
| Fahrmann et al. 2015 | GC | EI | – | TOF | – |
| Mazzone et al. 2016 | LC | ESI | positive | linear ion-trap | MS/MS |
| An et al. 2010 | LC | ESI | positive | Q-TOF | MS/MS |
| Moreno et al. 2018 | LC, GC | ESI, EI | positive, negative | LC: linear ion‐trap, GC: single‐quadrupole | LC: MS/MS |
| Moreno et al. 2018 | LC, GC | ESI, EI | positive, negative | LC: linear ion‐trap, GC: single‐quadrupole | LC: MS/MS |
| Wikoff et al. 2015b | GC | EI | – | TOF | – |
| Reference | Data processing software | Database search |
| Sappington et al. 2018 | MassHunter, MassProfilerProfessional | HMDB |
| Fahrmann et al. 2015 | – | UC Davis Metabolomics BinBase database |
| Maeda et al. 2010 | Xcalibur | – |
| Fahrmann et al. 2015 | – | UC Davis Metabolomics BinBase database |
| Miyamoto et al. 2015 | ChromaTOF software (Leco) | UC Davis Metabolomics BinBase database |
| Fahrmann et al. 2015 | – | UC Davis Metabolomics BinBase database |
| Klupczynska et al. 2016a | – | – |
| An et al. 2010 | MZmine 2 beta | HMDB, PubChem compound database, METLIN, KEGG |
| Miyamoto et al. 2015 | ChromaTOF software (Leco) | UC Davis Metabolomics BinBase database |
| Sappington et al. 2018 | MassHunter, MassProfilerProfessional | HMDB |
| Fahrmann et al. 2015 | – | UC Davis Metabolomics BinBase database |
| Mazzone et al. 2016 | Metabolon LIMS system | Metabolon LIMS system |
| An et al. 2010 | MZmine 2 beta | HMDB, PubChem compound database, METLIN, KEGG |
| Moreno et al. 2018 | – | KEGG, HMDB |
| Moreno et al. 2018 | – | KEGG, HMDB |
| Wikoff et al. 2015b | BinBase | NIST11, BinBase |
| Reference | Difference method | Mean concentration (case) | Mean concentration (control) | Fold change (case/control) | P-value | FDR | VIP |
| Sappington et al. 2018 | OPLS-DA, PLS-DA | – | – | 0.98 | 0.92 | – | – |
| Fahrmann et al. 2015 | regress (by the covariates: age, gender and smoking history [packs per year]), permutation test | 30367 ± 8595 | 30696 ± 10252 | 0.989 | 0.883 | 0.96 | – |
| Maeda et al. 2010 | Mann-Whitney U-test, PCA | 59.3 ± 12 μM | 59.8±10.9 μM | – | 0.67 | – | – |
| Fahrmann et al. 2015 | regress (by the covariates: age, gender and smoking history [packs per year]), permutation test | 14276 ± 4817 | 15614 ± 6000 | 0.91 | 0.505 | 0.74 | – |
| Miyamoto et al. 2015 | Analysis of Covariance | 126620.909090909 | 139425.727272727 | 0.908160291272708 | 0.390895321684418 | – | – |
| Fahrmann et al. 2015 | regress (by the covariates: age, gender and smoking history [packs per year]), permutation test | 30547 ± 10083 | 33738 ± 10507 | 0.91 | 0.269 | 0.6 | – |
| Klupczynska et al. 2016a | t-test, Welch’s t-test or the Mann-Whitney U test, one-way ANOVA | 42.43±13 ?M | 45.51±9.94 ?M | 0.93 | 0.0983 | – | – |
| An et al. 2010 | independent t-test | – | – | – | 0.014 | – | – |
| Miyamoto et al. 2015 | Analysis of Covariance | 121513.055555556 | 143382.65 | 0.847473913723561 | 0.00508079314680403 | – | – |
| Sappington et al. 2018 | OPLS-DA, PLS-DA | – | – | 0.59 | 0.0027 | – | – |
| Fahrmann et al. 2015 | regress (by the covariates: age, gender and smoking history [packs per year]), permutation test | 17526 ± 10639 | 24922 ± 9245 | 0.7 | 0.001 | 0.047 | – |
| Mazzone et al. 2016 | two- sample independent t test | 0.945816± 0.1884884 | 1.038218± 0.2242702 | 0.910999424013068 | 0.0006709 | 0.015006832 | – |
| An et al. 2010 | independent t-test | – | – | – | 0.00065 | – | – |
| Moreno et al. 2018 | paired two‐sample t‐test, PLS-DA | – | – | 2.1647293571205 | 0.0000052274965518423 | 0.0000118847357503423 | – |
| Moreno et al. 2018 | paired two‐sample t‐test, PLS-DA | – | – | 2.11885230771592 | 0.00000000814386903587192 | 0.000000274598387531254 | – |
| Wikoff et al. 2015b | OPLS-DA | – | – | 1.2 | – | 0.837 | – |
| Reference | Classification method | Cutoff value | AUROC 95%CI | Sensitivity (%) | Specificity (%) | Accuracy (%) |
| Sappington et al. 2018 | – | – | – | – | – | – |
| Fahrmann et al. 2015 | random forest | – | – | – | – | – |
| Maeda et al. 2010 | ROC curve | – | combination of 21 amino acid: 0.812 | – | – | – |
| Fahrmann et al. 2015 | random forest | – | maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan+adenosine-5-Phosphate=0.670 (0.552, 0.789) | 39.5 maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan=60.5 | 65.1 maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan=93.0 | 52.3 maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan=76.7 |
| Miyamoto et al. 2015 | – | – | – | – | – | – |
| Fahrmann et al. 2015 | random forest | – | – | – | – | – |
| Klupczynska et al. 2016a | ROC curve analysis (Monte-Carlo cross validation), discriminant function analysis | – | 0.572 | alanine+histidine+ornithine+isoleucine+tryptophan+valine=84.4 | alanine+histidine+ornithine+isoleucine+tryptophan+valine=52.4 | – |
| An et al. 2010 | – | – | – | – | – | – |
| Miyamoto et al. 2015 | – | – | – | – | – | – |
| Sappington et al. 2018 | – | – | – | – | – | – |
| Fahrmann et al. 2015 | random forest | – | maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan+adenosine-5-Phosphate=0.883 (0.812, 0.955) | – | – | 50.6 maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan=77.1 |
| Mazzone et al. 2016 | – | – | – | – | – | – |
| An et al. 2010 | – | – | – | – | – | – |
| Moreno et al. 2018 | – | – | – | – | – | – |
| Moreno et al. 2018 | – | – | – | – | – | – |
| Wikoff et al. 2015b | – | – | – | – | – | – |