Table 1.
Phytochemical profile of AIRME using chromatography techniques (HR-LC-MS and GC-MS), antioxidant descriptors (Hbds—Hydrogen bond donor count and Hbas—Hydrogen bond acceptors count) and adverse properties (Mut—mutagenicity, Tum—tumarogenicity, Irri—irritant and RepTox—reproductive toxicology) predicted using Marvin sketch, a computational tool.
| No | Compounds Identified by HR-LC-MS | RT | Formula | Mass | Hbds | Hbas | Mut | Tum | Irri | RepTox | PubChem CID | Percentage |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Oxtriphylline | 0.42 | C12H22N5O3 | 284.1715 | 1 | 4 | No | No | No | No | 656652 | 0.677 |
| 2 | Choline | 0.501 | C5H14NO | 104.1074 | 1 | 2 | No | No | No | No | 6209 | 0.847 |
| 3 | Bumetanide | 0.612 | C17H20N2O5S | 364.1112 | 3 | 7 | No | No | Yes | No | 2471 | 0.847 |
| 4 | Indospicine | 0.612 | C7H15N3O2 | 173.1165 | 4 | 4 | No | No | Yes | No | 108010 | 0.776 |
| 5 | 10-Hydroxy-2E,8E-Decadiene-4,6-diynoic acid | 0.613 | C10H12O3 | 180.0772 | 2 | 2 | No | No | Yes | No | 9543616 | 0.745 |
| 6 | 2,6-Piperidinedicarboxylic acid | 0.615 | C7H11NO4 | 173.069 | 2 | 4 | No | No | No | Yes | 557515 | 0.881 |
| 7 | Ala Ser His | 0.616 | C12H19N5O5 | 313.1392 | 6 | 7 | No | No | No | No | - | 0.644 |
| 8 | Arg Pro | 0.656 | C11H21N5O3 | 271.1652 | 5 | 7 | No | No | No | No | - | 0.677 |
| 9 | His Gly Val | 0.658 | C13H21N5O4 | 311.1577 | 5 | 6 | No | No | No | No | - | 0.627 |
| 10 | Pro Ile | 0.662 | C11H20N2O3 | 228.1459 | 4 | 4 | No | No | No | No | - | 0.661 |
| 11 | Fenofibrate | 0.669 | C20H21ClO4 | 360.116 | 0 | 3 | No | No | No | No | 3339 | 0.711 |
| 12 | Mycophenolic Acid | 0.671 | C17H20O6 | 320.1239 | 2 | 5 | No | No | No | No | 446541 | 0.881 |
| 13 | Mimosine | 0.673 | C8H10N2O4 | 198.0642 | 3 | 6 | low | No | No | No | 440473 | 0.911 |
| 14 | Dimethylglycine | 0.684 | C4H9NO2 | 103.0634 | 1 | 3 | No | No | No | No | 673 | 0.640 |
| 15 | 3,7-Epoxycaryophyllan-6-one | 0.688 | C15H24O2 | 236.1759 | 0 | 2 | No | No | No | No | 4330530 | 0.745 |
| 16 | l-2-Aminoadipic acid | 0.778 | C6H11NO4 | 161.0686 | 3 | 5 | No | No | No | No | 92136 | 0.474 |
| 17 | Trans-4-Hydroxy-L-proline | 0.869 | C5H9NO3 | 131.058 | 3 | 4 | No | No | No | No | 5810 | 0.372 |
| 18 | N2-Succinylglutamic acid | 0.883 | C9H13NO7 | 247.0694 | 4 | 7 | No | No | No | No | 25244383 | 0.406 |
| 19 | Mucronulatol((+/−)) | 1.157 | C17H18O5 | 302.111 | 2 | 5 | No | No | No | Yes | 442811 | 0.372 |
| 20 | Propionylglycine methyl ester | 1.698 | C6H11NO3 | 145.0738 | 1 | 2 | No | No | No | No | - | 1.186 |
| 21 | Ile Tyr | 1.744 | C15H22N2O4 | 294.1575 | 4 | 6 | No | No | No | No | - | 0.847 |
| 22 | Phendimetrazine | 1.855 | C12H17NO | 191.131 | 0 | 2 | No | No | No | No | 30487 | 1.016 |
| 23 | 4-(2-Hydroxy-3-isopropylaminopropyl)benzoic acid | 2.163 | C13H19NO4 | 253.1313 | 3 | 5 | No | No | No | No | - | 0.406 |
| 24 | Mexiletine | 2.219 | C11H17NO | 179.1309 | 0 | 1 | No | No | Yes | No | 4178 | 0.406 |
| 25 | N-(3-Oxo-octanoyl)homoserine lactone | 2.753 | C12H19NO4 | 241.1335 | 1 | 3 | No | No | Yes | No | 127293 | 0.474 |
| 26 | Retusoquinone | 3.071 | C11H12O | 160.0872 | 0 | 1 | No | No | No | No | 6111564 | 1.694 |
| 27 | Peucenin | 3.385 | C15H16O4 | 260.103 | 2 | 4 | No | No | No | No | 68477 | 0.949 |
| 28 | Dehydrovariabilin | 3.494 | C17H14O4 | 282.0845 | 0 | 3 | No | No | No | Yes | 624785 | 1.050 |
| 29 | Normeperidine | 3.598 | C14H19NO2 | 233.1414 | 1 | 2 | No | No | No | No | 32414 | 0.881 |
| 30 | Thr Ala Ser | 3.605 | C10H19N3O6 | 277.1311 | 6 | 7 | No | No | No | No | - | 1.016 |
| 31 | Diethyl Oxalpropionate | 3.711 | C9H14O5 | 202.0842 | 0 | 3 | No | No | No | No | 97750 | 0.881 |
| 32 | 3-O-Methylrimiterol | 3.763 | C13H19NO3 | 237.1366 | 3 | 4 | No | No | No | No | - | 1.118 |
| 33 | Citrulline n-butyl ester | 4.092 | C10H21N3O3 | 231.1582 | 3 | 3 | No | No | Yes | No | 6426971 | 0.542 |
| 34 | 2(Benzylmethylamino)Ethanol N-Oxide | 4.126 | C10H15NO2 | 181.1102 | 1 | 2 | No | No | No | No | 264996 | 0.372 |
| 35 | Chloramphenicol alcohol | 4.177 | C11H14N2O6 | 270.0845 | 4 | 6 | Yes | No | No | No | 10107147 | 0.406 |
| 36 | 12-Aminododecanoic acid | 4.41 | C12H25NO2 | 215.1891 | 2 | 3 | No | No | No | No | 69661 | 0.745 |
| 37 | 3-Oxa-9azoniatricyclo[3.3.1.02,4]non ane, 9-ethyl-9-methyl-7[(phenylacetyl)oxy] | 4.522 | C18H24NO3 | 302.1757 | 1 | 4 | No | No | No | No | - | 0.542 |
| 38 | 3,11-Dihydroxy myristoic acid | 4.835 | C14H28O4 | 260.2002 | 3 | 4 | No | No | No | No | 5282923 | 0.881 |
| 39 | Avocadene acetate | 4.835 | C19H36O4 | 328.2622 | 2 | 3 | No | No | Yes | No | 3624980 | 0.881 |
| 40 | Sulindac sulfide | 4.881 | C20H17FO2S | 340.0902 | 1 | 2 | No | No | No | No | 5352624 | 1.013 |
| 41 | 6-Methoxyquinoline | 4.928 | C10H9NO | 159.0686 | 0 | 2 | Yes | No | No | No | 14860 | 1.288 |
| 42 | Edrophonium | 4.928 | C10H16NO | 166.1233 | 1 | 1 | No | No | No | No | 3202 | 1.220 |
| 43 | Quinine | 4.939 | C20H24N2O2 | 324.1837 | 1 | 4 | No | No | No | No | 3034034 | 1.152 |
| 44 | 3-[2(Dimethylamino)ethoxy]phen ylmethyl]-4-methyl-phenol | 5.11 | C18H23NO2 | 285.173 | 1 | 3 | No | No | No | No | - | 1.050 |
| 45 | Metyrapol | 5.301 | C14H16N2O | 228.1292 | 1 | 3 | No | No | No | No | 161210 | 0.949 |
| 46 | Oxprenolol | 5.322 | C15H23NO3 | 265.1682 | 2 | 7 | No | No | Yes | No | 4631 | 1.118 |
| 47 | Oxyphencyclimine | 5.541 | C20H28N2O3 | 344.2094 | 1 | 6 | No | No | No | No | 4642 | 0.986 |
| 48 | Oxycodone | 6.166 | C18H21NO4 | 315.1486 | 1 | 9 | No | No | No | No | 5284603 | 0.406 |
| 49 | Ergoline-8-methanol, 10-methoxy-1,6-dimethyl | 6.279 | C18H24N2O2 | 300.1858 | 1 | 3 | No | No | No | Yes | - | 0.847 |
| 50 | Evoxine | 6.332 | C18H21NO6 | 347.136 | 2 | 10 | No | No | No | No | 73416 | 0.542 |
| 51 | 2-Hydroxytrimipramine | 6.339 | C20H26N2O | 310.2038 | 1 | 3 | No | No | No | No | 160610 | 0.474 |
| 52 | Penbutolol | 6.575 | C18H29NO2 | 291.2196 | 2 | 5 | Yes | No | No | No | 37464 | 1.152 |
| 53 | Ala Lys Ile | 6.581 | C15H30N4O4 | 330.23 | 7 | 10 | No | No | No | No | - | 1.322 |
| 54 | Oxymorphone | 6.76 | C17H19NO4 | 301.131 | 2 | 9 | No | No | No | No | 5284604 | 0.334 |
| 55 | Diamorphine (heroin) | 6.762 | C21H23NO5 | 369.1566 | 0 | 7 | No | No | No | Yes | 5462328 | 0.406 |
| 56 | Terbinafine metabolite | 6.911 | C19H23NO3 | 313.1672 | 3 | 5 | No | No | No | No | - | 1.098 |
| 57 | Strychnine | 6.912 | C21H22N2O2 | 334.1672 | 0 | 5 | No | No | No | No | 441071 | 1.050 |
| 58 | Hydrolysis product of bussein | 7.021 | C32H40O14 | 648.241 | 8 | 26 | No | No | low | No | 54699399 | 1.145 |
| 59 | Ambelline | 7.026 | C18H21NO5 | 331.1412 | 0 | 9 | Yes | No | No | No | 25092366 | 1.321 |
| 60 | 2-Pyrrolidinone, 4-(2aminoethyl)-1-ethyl-3,3diphenyl-(AHR 5904) | 7.039 | C20H24N2O | 308.1882 | 2 | 3 | No | No | No | No | 164917 | 1.023 |
| 61 | Glu Val Asp | 7.221 | C14H23N3O8 | 361.1518 | 7 | 17 | No | No | No | No | - | 0.953 |
| 62 | 10-Nitro,9Z,12Zoctadecadienoic acid | 7.339 | C18H31NO4 | 325.2246 | 1 | 8 | No | No | No | No | 5282259 | 0.994 |
| 63 | 5β-Chol-2-en-24oic Acid | 7.397 | C24H38O2 | 358.2954 | 1 | 4 | No | No | No | No | - | 0.912 |
| 64 | 5α-Cholan-24oic Acid | 7.733 | C24H40O2 | 360.311 | 1 | 4 | No | No | No | No | 5283802 | 0.832 |
| 65 | Etioporphyrin III | 7.793 | C32H38N4 | 478.317 | 2 | 4 | No | No | No | No | 141310 | 0.814 |
| 66 | Coproporphyrin II | 8.066 | C36H38N4O8 | 654.2548 | 6 | 10 | No | No | No | No | 165072 | 0.964 |
| 67 | Arg Ala Arg | 8.473 | C15H31N9O4 | 401.2552 | 15 | 15 | No | No | No | No | - | 0.456 |
| 68 | (5Z)-4,4-difluoro1alpha,25-dihydroxyvitamin D3/(5Z)-4,4-difluoro1alpha, 25dihydroxycholecalcifer | 8.766 | C27H42F2O3 | 452.304 | 3 | 6 | No | No | No | No | - | 0.754 |
| 69 | Arg Val Pro | 8.887 | C16H30N6O4 | 370.2321 | 8 | 12 | No | No | No | No | - | 1.101 |
| 70 | Dihydrodeoxystreptomycin | 9.017 | C21H41N7O11 | 567.2862 | 16 | 29 | No | No | No | No | 11953824 | 1.021 |
| 71 | Swietenine | 9.019 | C32H40O9 | 568.2704 | 1 | 10 | No | No | No | No | 76327465 | 1.134 |
| 72 | C16 Sphinganine | 9.686 | C16H35NO2 | 273.266 | 3 | 3 | No | No | No | No | 5283572 | 0.786 |
| 73 | (Z)-N-(2hydroxyethyl)hexadec-7- | 11.085 | 297.2658 | 2 | 2 | No | No | No | No | - | 0.354 | |
| 74 | N-Hexadecyl-l-hydroxyproline | 11.684 | C21H41NO3 | 355.307 | 3 | 4 | No | No | No | No | 66690736 | 0.834 |
| 75 | Trihexyphenidyl N-oxide | 12.227 | C20H31NO2 | 317.2342 | 1 | 2 | No | No | No | No | 129318457 | 0.965 |
| 76 | Zearalenone | 12.772 | C18H22O5 | 318.1478 | 2 | 4 | No | No | No | No | 5281576 | 0.236 |
| 77 | GPEtn(10:0/11:0)[U] | 12.813 | C26H52NO8P | 537.3399 | 2 | 4 | No | No | No | No | - | 0.875 |
| 78 | 25-Hydroxycholesterol(d3) | 12.829 | C27H43D3O2 | 405.3607 | 2 | 2 | No | No | low | No | - | 0.823 |
| 79 | Disopyramide | 13.729 | C21H29N3O | 339.2395 | 1 | 3 | No | No | No | No | 3114 | 0.787 |
| 80 | 12-Hydroxy-10octadecynoic acid | 13.763 | C18H32O3 | 296.2341 | 2 | 3 | No | No | No | No | - | 0.867 |
| 81 | Anandamide (18:3, n-6) | 14.295 | C20H35NO2 | 321.2652 | 2 | 2 | No | No | No | No | 5283445 | 0.564 |
| 82 | 9-Hydroxy-12-oxo10-octadecenoic acid | 14.4 | C18H32O4 | 312.2287 | 2 | 4 | No | No | No | No | 5282968 | 0.753 |
| 83 | 13-OxoODE | 14.417 | C18H30O3 | 294.2184 | 1 | 3 | No | No | Yes | No | 5283012 | 0.700 |
| 84 | 2R-hydroxy9Z,12Z,15Z-octadecatrienoic acid | 14.648 | C18H30O3 | 294.2188 | 2 | 3 | No | No | No | No | 16061058 | 1.032 |
| 85 | Lactone of PGFMUM | 14.85 | C16H24O5 | 296.1612 | 1 | 4 | No | No | No | No | - | 0.854 |
| 86 | N Acetylsphingosine | 15.403 | C20H39NO3 | 341.2915 | 3 | 3 | No | No | No | No | 5497136 | 1.132 |
| 87 | Phytosphingosine | 16.285 | C18H39NO3 | 317.2918 | 4 | 4 | No | No | No | No | 122121 | 0.126 |
| 88 | Dihydroceramide C2 | 16.767 | C20H41NO3 | 343.3073 | 3 | 3 | No | No | No | No | 6610273 | 0.453 |
| 89 | 3-Deacetyl Khivorin | 16.926 | C30H40O9 | 544.2667 | 1 | 5 | No | No | No | No | 46878892 | 0.763 |
| 90 | Harderoporphyrin | 17.931 | C35H36N4O6 | 608.2594 | 5 | 8 | No | No | No | No | 3081462 | 0.998 |
| 91 | His Arg Val | 18.001 | C17H30N8O4 | 410.2411 | 8 | 9 | No | No | No | No | - | 0.324 |
| 92 | Harderoporphyrinogen | 18.177 | C35H42N4O6 | 614.3115 | 4 | 9 | No | No | Yes | No | 193825 | 0.231 |
| 93 | Ramipril glucuronide | 18.404 | C29H40N2O11 | 592.2643 | 5 | 10 | No | No | No | No | - | 1.563 |
| 94 | Deoxykhivorin | 18.791 | C32H42O9 | 570.282 | 0 | 4 | No | No | No | No | 6708722 | 0.232 |
| 95 | Antimycin A (A1 shown) | 19.021 | C27H38N2O9 | 534.2592 | 3 | 6 | No | No | Yes | No | 12550 | 1.324 |
| 96 | N-(2hydroxyethyl)icosanamide | 19.051 | C22H45NO2 | 355.3432 | 2 | 2 | No | No | No | No | 3787294 | 1.021 |
| 97 | 9,14,19,19,19Pentadeuterio-1α,25dihydroxyprevitamin D3 / 9,14,19,19,19-pentadeuterio1alpha,25 | 19.24 | C27H39D5O3 | 421.355 | 1 | 1 | No | No | low | No | - | 1.240 |
| 98 | 2Tricosanamidoethanesulfonic acid | 19.241 | C25H51NO4S | 461.3489 | 2 | 4 | No | No | No | No | - | 1.200 |
| 99 | Trandolapril glucuronide | 20.16 | C30H42N2O11 | 606.2793 | 5 | 10 | No | No | No | No | 92023960 | 0.932 |
| 100 | 2,4,6-Trimethyl-2,15tetracosadienoic acid | 20.184 | C27H50O2 | 406.3821 | 1 | 2 | No | No | No | No | - | 0.901 |
| 101 | 3β,6α,7αTrihydroxy-5β-cholan-24oic Acid | 20.754 | C24H40O5 | 408.2845 | 4 | 5 | No | No | No | No | - | 0.875 |
| Compounds Identified by GC-MS | ||||||||||||
| 1 | Piperidine-2,5-dione | 8.97 | C5H7NO2 | 113.047 | 1 | 2 | No | No | No | No | 533930 | 3.733 |
| 2 | Phenol, 2,4-bis(1,1-dimethylethyl)- | 12.53 | C14H22O | 206.167 | 1 | 1 | No | No | No | No | 528937 | 1.333 |
| 3 | Tridecanoic acid,12-methyl-, methyl ester | 14.92 | C15H30O2 | 242.224 | 0 | 1 | No | No | No | No | 21204 | 1.200 |
| 4 | 1-Oxacyclopentadecan-2-one,15,15-dimethyl | 15.63 | C16H30O2 | 254.224 | 0 | 1 | No | No | No | No | - | 0.800 |
| 5 | 11-Hexadecenoic acid, methyl ester | 16.88 | C17H32O2 | 268.24 | 0 | 1 | No | No | No | No | 5364696 | 1.040 |
| 6 | Pentadecanoic acid, 14-methyl-, methyl ester | 17.08 | C17H34O2 | 270.255 | 0 | 1 | No | No | No | No | 21205 | 1.493 |
| 7 | Octadecanoic acid | 17.78 | C19H38O2 | 298.287 | 0 | 1 | No | No | No | No | 5281 | 2.053 |
| 8 | 13-Hexyloxacyclotridec-10-en-2-one | 18.52 | C18H30O2 | 278.224 | 0 | 1 | No | No | No | No | 5369119 | 1.066 |
| 9 | 10-Octadecenoic acid,methyl ester | 18.82 | C19H36O2 | 296.271 | 0 | 1 | No | No | No | No | 5364425 | 1.954 |
| 10 | Octadecanoic acid,methyl ester | 19.05 | C19H38O2 | 298.287 | 0 | 1 | No | No | No | No | 8201 | 0.956 |
| 11 | Dasycarpidan-1-methanol,acetate (ester) | 20.37 | C20H26N2O2 | 326.44 | 1 | 2 | No | No | No | No | 550072 | 0.543 |
| 12 | Aspidospermidine-3-carboxylic acid, 2,3-didehydro-,methyl ester,[5a,12a,19a]- | 20.65 | C21H26N2O2 | 338.199 | 1 | 3 | No | No | No | No | - | 2.123 |
| 13 | Cephalotaxine, 3-deoxy-3,11-epoxy-, (3a,11a)- | 22.96 | C18H19NO4 | 313.131 | 0 | 5 | No | No | No | No | - | 2.666 |
| 14 | 4-H-1-Benzopyran-4-one, 7-(acetyloxy)-2-(4-(acetyloxy)phenyl)-5-methoxy- | 25.6 | C19H14O7 | 354.073 | 1 | 5 | Yes | No | No | Yes | - | 2.456 |