1194:
427:
264:
927:
1170:
1079:
51:
1072:
1065:
1058:
60:
1010:) is poured onto the activated charcoal-adenine structure to liberate the adenine into the ammonia-water solution. The solution containing water, ammonia, and adenine is then left to air dry, with the adenine losing solubility due to the loss of ammonia gas that previously made the solution basic and capable of dissolving adenine, thus causing it to crystallize into a pure white powder that can be stored.
1163:
723:
38:
1005:
that interact between the adenine and the carbon in the charcoal. Because charcoal has a large surface area, it's able to capture the majority of molecules that pass a certain size (greater than water and formamide) through it. To extract the adenine from the charcoal-adsorbed adenine, ammonia gas
1000:
as an acid catalyst and sunlight or ultraviolet conditions. After the 5 hours have passed and the formamide-phosphorus oxychloride-adenine solution cools down, water is put into the flask containing the formamide and now-formed adenine. The water-formamide-adenine solution is then poured through a
705:
1001:
filtering column of activated charcoal. The water and formamide molecules, being small molecules, will pass through the charcoal and into the waste flask; the large adenine molecules, however, will attach or "adsorb" to the charcoal due to the
1413:
M. J. Nowak; H. Rostkowska; L. Lapinski; J. S. Kwiatkowski; J. Leszczynski (1994). "Experimental matrix isolation and theoretical ab initio HF/6-31G(d, p) studies of infrared spectra of purine, adenine and 2-chloroadenine".
1312:. In 2011, physicists reported that adenine has an "unexpectedly variable range of ionization energies along its reaction pathways" which suggested that "understanding experimental data on how adenine survives exposure to
938:, compounds that can be rapidly interconverted and are often considered equivalent. However, in isolated conditions, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.
1461:
1872:
2196:
2128:
2420:
2273:
1197:
Adenine on Crick and Watson's DNA molecular model, 1953. The picture is shown upside down compared to most modern drawings of adenine, such as those used in this article.
2415:
2405:
992:
under 120 degree
Celsius conditions within a sealed flask for 5 hours to form adenine. The reaction is heavily increased in quantity by using a phosphorus oxychloride (
2316:
2239:
2288:
1865:
988:
Patented Aug. 20, 1968, the current recognized method of industrial-scale production of adenine is a modified form of the formamide method. This method heats up
1858:
736:
2085:
1719:
2080:
1378:
Plützer, Chr.; Kleinermanns, K. (2002). "Tautomers and electronic states of jet-cooled adenine investigated by double resonance spectroscopy".
476:
1573:
Oro J, Kimball AP (August 1961). "Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide".
1193:
3083:
642:
312:
1133:
are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring
791:
2457:
1208:. Due to it being synthesized by the body and not essential to be obtained by diet, it does not meet the definition of
894:
sugar and the bottom left nitrogen (thereby removing the existing hydrogen atom). The remaining structure is called an
1225:
844:
441:
3100:
1845:
731:
743:
2772:
2219:
2214:
1146:
142:
2357:
2171:
2166:
384:
259:
2781:
2763:
2395:
2390:
2186:
1229:
848:
405:
201:
2410:
2306:
2301:
2191:
2181:
599:
1727:
2321:
271:
1659:
Callahan MP, Smith KE, Cleaves HJ, Ruzicka J, Stern JC, Glavin DP, House CH, Dworkin JP (Aug 2011).
2594:
2148:
997:
422:
3088:
2377:
2335:
2176:
2123:
2118:
1776:
1749:
1126:
841:
149:
2450:
2400:
2352:
2347:
2138:
1957:
1797:, Ullrich S (2011). "Ionization potentials of adenine along the internal conversion pathways".
1122:
837:
886:
The adjacent image shows pure adenine, as an independent molecule. When connected into DNA, a
2367:
2311:
2268:
2263:
2133:
1150:
954:
3127:
3049:
2829:
2553:
2372:
2362:
2283:
1806:
1672:
1617:
1423:
1387:
1250:
aden "gland", in reference to the pancreas, from which Kossel's sample had been extracted.
1233:
1043:
856:
833:
393:
78:
8:
2943:
2278:
2158:
2047:
1950:
1002:
993:
221:
108:
1810:
1676:
1621:
1427:
1391:
1316:
is much more complicated than previously thought"; these findings have implications for
181:
118:
2722:
2617:
2024:
1695:
1660:
1641:
1501:
1476:
1217:
1138:
426:
263:
161:
3137:
3009:
2984:
2443:
2234:
2206:
1822:
1700:
1633:
1590:
1586:
1506:
1439:
1435:
1313:
1305:
946:
699:
1645:
1412:
3132:
3019:
2994:
2914:
2004:
1814:
1690:
1680:
1625:
1608:
Shapiro, Robert (June 1995). "The prebiotic role of adenine: A critical analysis".
1582:
1496:
1488:
1431:
1395:
1266:
1007:
977:
958:
761:
571:
504:
2694:
2689:
2684:
1457:
3024:
2581:
2566:
1994:
1923:
1240:
1134:
1130:
805:
290:
2672:
2667:
2662:
2657:
1525:
1042:
to assist in stabilizing the nucleic acid structures. In RNA, which is used for
357:
3094:
3014:
2727:
2540:
2110:
2060:
2055:
1976:
1794:
1665:
Proceedings of the
National Academy of Sciences of the United States of America
1270:
1258:
1244:
1114:
911:
714:
1661:"Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases"
687:
3121:
2863:
2853:
2838:
2558:
2229:
2224:
2143:
2075:
2014:
1443:
1039:
973:
887:
623:
560:
252:
2501:
2496:
1850:
1685:
3069:
2989:
2948:
2901:
2868:
2848:
2843:
2704:
2632:
2622:
2612:
2470:
2070:
1913:
1881:
1826:
1754:
1704:
1637:
1594:
1510:
1321:
1317:
1269:(HCN) molecules in aqueous solution; whether this has implications for the
1031:
829:
809:
592:
1777:"Physicists Uncover New Data On Adenine, a Crucial Building Block of Life"
1549:
3001:
2858:
2679:
2571:
1309:
1118:
915:
891:
1257:
have shown that a large quantity of adenine can be synthesized from the
1254:
241:
2939:
2931:
2924:
2888:
2881:
2808:
2754:
2736:
2652:
2627:
2601:
2576:
2535:
2099:
2037:
2032:
1967:
1930:
1890:
1818:
1629:
1550:"adenine | Etymology, origin and meaning of adenine by etymonline"
1285:
1221:
1106:
1027:
1019:
962:
852:
582:
532:
302:
272:
212:
24:
1492:
565:
360 to 365 °C (680 to 689 °F; 633 to 638 K) decomposes
3044:
3036:
2953:
2919:
2745:
2714:
2644:
2521:
2511:
2488:
2065:
1989:
1984:
1399:
1213:
1142:
1102:
989:
969:
899:
20:
1354:
713:
Except where otherwise noted, data are given for materials in their
2822:
2009:
1945:
1918:
935:
926:
821:
332:
232:
50:
1750:"DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests"
148:
141:
2506:
2466:
2435:
2019:
1999:
1940:
1908:
1301:
1262:
1209:
1169:
1078:
1035:
1023:
965:
950:
868:
825:
817:
588:
550:
344:
59:
2979:
2966:
2896:
1935:
1898:
1524:
texte, Deutsche chemische
Gesellschaft Auteur du (1885-01-01).
1110:
1071:
1064:
1057:
1047:
930:
Adenine structure, with standard numbering of positions in red.
903:
876:
802:
450:
InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
192:
460:
InChI=1/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
1377:
1289:
1274:
368:
172:
131:
1720:"NASA Researchers: DNA Building Blocks Can Be Made in Space"
1459:, "Process for preparing adenine", issued 1966-11-10
410:
1723:
1658:
1281:
1162:
953:. Both adenine and guanine are derived from the nucleotide
323:
1526:"Berichte der Deutschen chemischen Gesellschaft zu Berlin"
37:
1297:
1293:
907:
880:
872:
864:
860:
813:
779:
773:
767:
957:(IMP), which in turn is synthesized from a pre-existing
782:
776:
1224:, bind with adenine to form the essential cofactors
770:
764:
311:
1747:
1416:Spectrochimica Acta Part A: Molecular Spectroscopy
1236:was one of the early scientists to study adenine.
1201:In older literature, adenine was sometimes called
867:. The shape of adenine is complementary to either
3119:
356:
1793:
961:through a complex pathway using atoms from the
828:(T). Adenine derivatives have various roles in
117:
1292:, was published suggesting building blocks of
2451:
1880:
1866:
1308:) may have been formed extraterrestrially in
1717:
1711:
1610:Origins of Life and Evolution of Biospheres
808:. It is one of the four nucleobases in the
2577:Calcitriol (1,25-dihydroxycholecalciferol)
2458:
2444:
1873:
1859:
1572:
425:
262:
220:
1694:
1684:
1500:
392:
1774:
1652:
1192:
925:
1607:
1575:Archives of Biochemistry and Biophysics
1141:. ATP is thus a derivative of adenine,
983:
421:
240:
3120:
1768:
1474:
1280:On August 8, 2011, a report, based on
949:involves the formation of adenine and
836:, in the form of both the energy-rich
253:
2439:
1854:
1523:
1324:compounds, according to one report.
453:Key: GFFGJBXGBJISGV-UHFFFAOYSA-N
200:
180:
1748:ScienceDaily Staff (9 August 2011).
1799:Physical Chemistry Chemical Physics
1741:
1718:Steigerwald, John (8 August 2011).
545:white to light yellow, crystalline
463:Key: GFFGJBXGBJISGV-UHFFFAOYAT
347:
331:
13:
2773:2-Methylnaphthalene-1,4-diamine (K
2465:
1216:complex. However, two B vitamins,
58:
49:
14:
3149:
1839:
1253:Experiments performed in 1961 by
1226:nicotinamide adenine dinucleotide
1018:Adenine is one of the two purine
845:nicotinamide adenine dinucleotide
612:4.15 (secondary), 9.80 (primary)
1344:, Oxford, Clarendon Press, 1959.
1168:
1161:
1077:
1070:
1063:
1056:
898:, as part of a larger molecule.
760:
721:
522:
516:
36:
16:Chemical compound in DNA and RNA
1601:
941:
859:and as a chemical component of
717:(at 25 °C , 100 kPa).
2782:4-Amino-3-methyl-1-naphthol (K
2764:4-Amino-2-methyl-1-naphthol (K
1775:Williams P (August 18, 2011).
1566:
1542:
1517:
1468:
1450:
1406:
1371:
1347:
1334:
1147:cyclic adenosine monophosphate
591:, soluble in hot water and/or
510:
1:
1342:Data for Biochemical Research
1327:
1212:and is no longer part of the
1587:10.1016/0003-9861(61)90033-9
1436:10.1016/0584-8539(94)80030-8
921:
7:
1477:"The assay of vitamin B(4)"
1230:flavin adenine dinucleotide
1034:. In DNA, adenine binds to
1013:
855:. It also has functions in
849:flavin adenine dinucleotide
676:or concentration (LD, LC):
45:
10:
3154:
2103:(Nucleoside monophosphate)
1188:
976:, as well as the coenzyme
537:135.13 g/mol
18:
3078:
3062:
3035:
2807:
2798:
2713:
2643:
2572:25-hydroxycholecalciferol
2520:
2487:
2478:
2386:
2343:
2334:
2297:
2259:
2252:
2205:
2157:
2109:
2098:
2046:
1975:
1966:
1958:Unnatural base pair (UBP)
1889:
711:
672:
667:
616:
497:
472:
437:
101:
93:
77:
72:
44:
35:
1340:Dawson, R.M.C., et al.,
1239:It was named in 1885 by
998:phosphorus pentachloride
902:is adenine reacted with
816:, the other three being
19:Not to be confused with
2336:Nucleoside triphosphate
1686:10.1073/pnas.1106493108
1481:The Biochemical Journal
1355:"MedlinePlus: Genetics"
1127:nucleoside triphosphate
918:, as used to form DNA.
914:is adenine attached to
2289:Xanthosine diphosphate
2253:Nucleoside diphosphate
1846:Vitamin B4 MS Spectrum
1380:Phys. Chem. Chem. Phys
1198:
1123:adenosine triphosphate
934:Adenine forms several
931:
838:adenosine triphosphate
694:227 mg/kg (rat, oral)
555:1.6 g/cm (calculated)
63:
54:
2595:Dihydroergocalciferol
1232:(FAD), respectively.
1196:
1151:adenosine diphosphate
955:inosine monophosphate
929:
62:
53:
3050:Dehydroascorbic acid
2554:7-Dehydrocholesterol
1234:Hermann Emil Fischer
1095:A-Ψ-Base-pair (RNA)
1092:A-D-Base-pair (RNA)
1089:A-U-Base-pair (RNA)
1086:A-T-Base-pair (DNA)
1006:dissolved in water (
1003:van der Waals forces
984:Manufacturing method
834:cellular respiration
79:Preferred IUPAC name
2944:Pyridoxal phosphate
2159:Deoxyribonucleotide
2048:Deoxyribonucleoside
1951:Pyrimidine analogue
1811:2011PCCP...1315492B
1805:(34): 15492–15900.
1677:2011PNAS..10813995C
1622:1995OLEB...25...83S
1428:1994AcSpA..50.1081N
1392:2002PCCP....4.4877P
1180:Deoxyadenosine, dA
1109:, when attached to
1046:, adenine binds to
994:phosphoryl chloride
572:Solubility in water
162:Beilstein Reference
32:
3105:Never to phase III
2618:Dihydrotachysterol
1819:10.1039/C1CP21350D
1630:10.1007/BF01581575
1554:www.etymonline.com
1199:
1139:chemical reactions
1026:) used in forming
932:
890:is formed between
744:Infobox references
484:NC1=NC=NC2=C1N=CN2
64:
55:
30:
3115:
3114:
3058:
3057:
3010:Adenosylcobalamin
2985:Dihydrofolic acid
2794:
2793:
2433:
2432:
2429:
2428:
2330:
2329:
2248:
2247:
2207:Cyclic nucleotide
2094:
2093:
1493:10.1042/bj0241827
1475:Reader V (1930).
1386:(20): 4877–4882.
1306:organic molecules
1277:is under debate.
1184:
1183:
1117:when attached to
1099:
1098:
1044:protein synthesis
1022:(the other being
947:Purine metabolism
857:protein synthesis
752:Chemical compound
750:
749:
700:Safety data sheet
406:CompTox Dashboard
150:Interactive image
143:Interactive image
68:
67:
3145:
3020:Hydroxocobalamin
2995:Levomefolic acid
2915:Pantothenic acid
2805:
2804:
2728:Phylloquinone (K
2485:
2484:
2460:
2453:
2446:
2437:
2436:
2341:
2340:
2257:
2256:
2107:
2106:
2028:-Methyladenosine
2005:5-Methylcytidine
1973:
1972:
1875:
1868:
1861:
1852:
1851:
1833:
1830:
1790:
1788:
1787:
1772:
1766:
1765:
1763:
1762:
1745:
1739:
1738:
1736:
1735:
1726:. Archived from
1715:
1709:
1708:
1698:
1688:
1656:
1650:
1649:
1605:
1599:
1598:
1570:
1564:
1563:
1561:
1560:
1546:
1540:
1539:
1537:
1536:
1521:
1515:
1514:
1504:
1472:
1466:
1465:
1464:
1460:
1454:
1448:
1447:
1422:(6): 1081–1094.
1410:
1404:
1403:
1400:10.1039/b204595h
1375:
1369:
1368:
1366:
1365:
1351:
1345:
1338:
1320:measurements of
1267:hydrogen cyanide
1172:
1165:
1158:
1157:
1131:phosphate groups
1081:
1074:
1067:
1060:
1053:
1052:
978:tetrahydrofolate
959:ribose phosphate
789:
788:
785:
784:
781:
778:
775:
772:
769:
766:
734:
728:
725:
724:
659:
636:147.0 J/(K·mol)
632:
617:Thermochemistry
524:
518:
512:
505:Chemical formula
430:
429:
414:
412:
396:
360:
349:
335:
315:
291:Gmelin Reference
274:
266:
255:
244:
224:
204:
184:
152:
145:
121:
46:
40:
33:
29:
3153:
3152:
3148:
3147:
3146:
3144:
3143:
3142:
3118:
3117:
3116:
3111:
3110:
3095:Clinical trials
3074:
3054:
3031:
3025:Methylcobalamin
3005:
2976:
2963:
2935:
2911:
2892:
2878:
2833:
2819:
2800:
2790:
2785:
2776:
2767:
2758:
2749:
2740:
2737:Menaquinones (K
2731:
2709:
2639:
2605:
2591:
2582:Calcitroic acid
2567:Cholecalciferol
2562:
2550:
2532:
2516:
2480:
2474:
2464:
2434:
2425:
2382:
2326:
2293:
2244:
2201:
2153:
2102:
2090:
2086:Deoxyxanthosine
2042:
1995:5-Methyluridine
1962:
1924:Purine analogue
1885:
1879:
1842:
1837:
1836:
1785:
1783:
1773:
1769:
1760:
1758:
1746:
1742:
1733:
1731:
1716:
1712:
1671:(34): 13995–8.
1657:
1653:
1606:
1602:
1571:
1567:
1558:
1556:
1548:
1547:
1543:
1534:
1532:
1522:
1518:
1473:
1469:
1462:
1456:
1455:
1451:
1411:
1407:
1376:
1372:
1363:
1361:
1359:medlineplus.gov
1353:
1352:
1348:
1339:
1335:
1330:
1241:Albrecht Kossel
1206:
1191:
1135:chemical energy
1016:
986:
944:
924:
896:adenine residue
806:nucleotide base
763:
759:
753:
746:
741:
740:
739: ?)
730:
726:
722:
718:
691:
685:
660:
657:
651:
647:
644:
643:Std enthalpy of
633:
626:
608:
577:0.103 g/100 mL
574:
527:
521:
515:
507:
493:
490:
485:
480:
479:
468:
465:
464:
461:
455:
454:
451:
445:
444:
433:
415:
408:
399:
379:
363:
350:
338:
318:
305:
293:
284:
247:
227:
207:
187:
164:
155:
135:
124:
111:
97:
89:
88:
28:
17:
12:
11:
5:
3151:
3141:
3140:
3135:
3130:
3113:
3112:
3109:
3108:
3107:
3106:
3103:
3092:
3086:
3080:
3079:
3076:
3075:
3073:
3072:
3066:
3064:
3060:
3059:
3056:
3055:
3053:
3052:
3047:
3041:
3039:
3033:
3032:
3030:
3029:
3028:
3027:
3022:
3017:
3015:Cyanocobalamin
3012:
3003:
2999:
2998:
2997:
2992:
2987:
2982:
2974:
2971:
2970:
2969:
2961:
2958:
2957:
2956:
2951:
2946:
2933:
2929:
2928:
2927:
2922:
2917:
2909:
2906:
2905:
2904:
2899:
2890:
2886:
2885:
2884:
2876:
2873:
2872:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2831:
2827:
2826:
2825:
2817:
2813:
2811:
2802:
2796:
2795:
2792:
2791:
2789:
2788:
2783:
2779:
2774:
2770:
2765:
2761:
2756:
2752:
2747:
2743:
2738:
2734:
2729:
2725:
2723:Naphthoquinone
2719:
2717:
2711:
2710:
2708:
2707:
2702:
2701:
2700:
2697:
2692:
2687:
2677:
2676:
2675:
2670:
2665:
2660:
2649:
2647:
2641:
2640:
2638:
2637:
2636:
2635:
2630:
2625:
2620:
2615:
2607:
2603:
2599:
2598:
2597:
2589:
2586:
2585:
2584:
2579:
2574:
2569:
2564:
2560:
2556:
2548:
2545:
2544:
2543:
2541:Ergocalciferol
2538:
2530:
2526:
2524:
2518:
2517:
2515:
2514:
2509:
2504:
2499:
2493:
2491:
2482:
2476:
2475:
2463:
2462:
2455:
2448:
2440:
2431:
2430:
2427:
2426:
2424:
2423:
2418:
2413:
2408:
2403:
2398:
2393:
2387:
2384:
2383:
2381:
2380:
2375:
2370:
2365:
2360:
2355:
2350:
2344:
2338:
2332:
2331:
2328:
2327:
2325:
2324:
2319:
2314:
2309:
2304:
2298:
2295:
2294:
2292:
2291:
2286:
2281:
2276:
2271:
2266:
2260:
2254:
2250:
2249:
2246:
2245:
2243:
2242:
2237:
2232:
2227:
2222:
2217:
2211:
2209:
2203:
2202:
2200:
2199:
2194:
2189:
2184:
2179:
2174:
2169:
2163:
2161:
2155:
2154:
2152:
2151:
2146:
2141:
2136:
2131:
2126:
2121:
2115:
2113:
2111:Ribonucleotide
2104:
2096:
2095:
2092:
2091:
2089:
2088:
2083:
2078:
2073:
2068:
2063:
2061:Deoxyguanosine
2058:
2056:Deoxyadenosine
2052:
2050:
2044:
2043:
2041:
2040:
2035:
2030:
2022:
2017:
2012:
2007:
2002:
1997:
1992:
1987:
1981:
1979:
1977:Ribonucleoside
1970:
1964:
1963:
1961:
1960:
1955:
1954:
1953:
1948:
1943:
1938:
1928:
1927:
1926:
1921:
1916:
1911:
1906:
1895:
1893:
1887:
1886:
1878:
1877:
1870:
1863:
1855:
1849:
1848:
1841:
1840:External links
1838:
1835:
1834:
1832:
1831:
1767:
1740:
1710:
1651:
1616:(1–3): 83–98.
1600:
1565:
1541:
1516:
1487:(6): 1827–31.
1467:
1449:
1405:
1370:
1346:
1332:
1331:
1329:
1326:
1271:origin of life
1259:polymerization
1204:
1190:
1187:
1186:
1185:
1182:
1181:
1178:
1174:
1173:
1166:
1115:deoxyadenosine
1101:Adenine forms
1097:
1096:
1093:
1090:
1087:
1083:
1082:
1075:
1068:
1061:
1040:hydrogen bonds
1015:
1012:
985:
982:
943:
940:
923:
920:
912:Deoxyadenosine
840:(ATP) and the
751:
748:
747:
742:
720:
719:
715:standard state
712:
709:
708:
703:
696:
695:
692:
683:
681:
678:
677:
670:
669:
665:
664:
661:
655:
649:
641:
638:
637:
634:
622:
619:
618:
614:
613:
610:
606:
596:
595:
587:negligible in
585:
579:
578:
575:
570:
567:
566:
563:
557:
556:
553:
547:
546:
543:
539:
538:
535:
529:
528:
525:
519:
513:
508:
503:
500:
499:
495:
494:
492:
491:
489:Nc1c2ncNc2ncn1
488:
486:
483:
475:
474:
473:
470:
469:
467:
466:
462:
459:
458:
456:
452:
449:
448:
440:
439:
438:
435:
434:
432:
431:
418:
416:
404:
401:
400:
398:
397:
389:
387:
381:
380:
378:
377:
373:
371:
365:
364:
362:
361:
353:
351:
343:
340:
339:
337:
336:
328:
326:
320:
319:
317:
316:
308:
306:
301:
298:
297:
294:
289:
286:
285:
283:
282:
278:
276:
268:
267:
257:
249:
248:
246:
245:
237:
235:
229:
228:
226:
225:
217:
215:
209:
208:
206:
205:
197:
195:
189:
188:
186:
185:
177:
175:
169:
168:
165:
160:
157:
156:
154:
153:
146:
138:
136:
129:
126:
125:
123:
122:
114:
112:
107:
104:
103:
99:
98:
95:
91:
90:
87:-Purin-6-amine
82:
81:
75:
74:
70:
69:
66:
65:
56:
42:
41:
15:
9:
6:
4:
3:
2:
3150:
3139:
3136:
3134:
3131:
3129:
3126:
3125:
3123:
3104:
3102:
3099:
3098:
3096:
3093:
3090:
3087:
3085:
3082:
3081:
3077:
3071:
3070:Multivitamins
3068:
3067:
3065:
3061:
3051:
3048:
3046:
3045:Ascorbic acid
3043:
3042:
3040:
3038:
3034:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3007:
3006:
3000:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2977:
2972:
2968:
2965:
2964:
2959:
2955:
2952:
2950:
2947:
2945:
2941:
2938:
2937:
2936:
2930:
2926:
2923:
2921:
2918:
2916:
2913:
2912:
2907:
2903:
2900:
2898:
2895:
2894:
2893:
2887:
2883:
2880:
2879:
2874:
2870:
2867:
2865:
2864:Prosultiamine
2862:
2860:
2857:
2855:
2854:Fursultiamine
2852:
2850:
2847:
2845:
2842:
2840:
2839:Acefurtiamine
2837:
2836:
2835:
2828:
2824:
2821:
2820:
2815:
2814:
2812:
2810:
2806:
2803:
2797:
2787:
2780:
2778:
2771:
2769:
2762:
2760:
2753:
2751:
2744:
2742:
2735:
2733:
2726:
2724:
2721:
2720:
2718:
2716:
2712:
2706:
2703:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2682:
2681:
2678:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2655:
2654:
2651:
2650:
2648:
2646:
2642:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2611:
2610:
2608:
2606:
2600:
2596:
2593:
2592:
2587:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2557:
2555:
2552:
2551:
2546:
2542:
2539:
2537:
2534:
2533:
2528:
2527:
2525:
2523:
2519:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2494:
2492:
2490:
2486:
2483:
2477:
2472:
2468:
2461:
2456:
2454:
2449:
2447:
2442:
2441:
2438:
2422:
2419:
2417:
2414:
2412:
2409:
2407:
2404:
2402:
2399:
2397:
2394:
2392:
2389:
2388:
2385:
2379:
2376:
2374:
2371:
2369:
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2345:
2342:
2339:
2337:
2333:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2299:
2296:
2290:
2287:
2285:
2282:
2280:
2277:
2275:
2272:
2270:
2267:
2265:
2262:
2261:
2258:
2255:
2251:
2241:
2238:
2236:
2233:
2231:
2228:
2226:
2223:
2221:
2218:
2216:
2213:
2212:
2210:
2208:
2204:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2164:
2162:
2160:
2156:
2150:
2147:
2145:
2142:
2140:
2137:
2135:
2132:
2130:
2127:
2125:
2122:
2120:
2117:
2116:
2114:
2112:
2108:
2105:
2101:
2097:
2087:
2084:
2082:
2079:
2077:
2076:Deoxycytidine
2074:
2072:
2069:
2067:
2064:
2062:
2059:
2057:
2054:
2053:
2051:
2049:
2045:
2039:
2036:
2034:
2031:
2029:
2027:
2023:
2021:
2018:
2016:
2015:Pseudouridine
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1982:
1980:
1978:
1974:
1971:
1969:
1965:
1959:
1956:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1933:
1932:
1929:
1925:
1922:
1920:
1917:
1915:
1912:
1910:
1907:
1905:
1902:
1901:
1900:
1897:
1896:
1894:
1892:
1888:
1883:
1876:
1871:
1869:
1864:
1862:
1857:
1856:
1853:
1847:
1844:
1843:
1828:
1824:
1820:
1816:
1812:
1808:
1804:
1800:
1796:
1792:
1791:
1782:
1781:Science Daily
1778:
1771:
1757:
1756:
1751:
1744:
1730:on 2015-06-23
1729:
1725:
1721:
1714:
1706:
1702:
1697:
1692:
1687:
1682:
1678:
1674:
1670:
1666:
1662:
1655:
1647:
1643:
1639:
1635:
1631:
1627:
1623:
1619:
1615:
1611:
1604:
1596:
1592:
1588:
1584:
1581:(2): 217–27.
1580:
1576:
1569:
1555:
1551:
1545:
1531:
1527:
1520:
1512:
1508:
1503:
1498:
1494:
1490:
1486:
1482:
1478:
1471:
1458:
1453:
1445:
1441:
1437:
1433:
1429:
1425:
1421:
1417:
1409:
1401:
1397:
1393:
1389:
1385:
1381:
1374:
1360:
1356:
1350:
1343:
1337:
1333:
1325:
1323:
1319:
1318:spectroscopic
1315:
1311:
1307:
1303:
1299:
1295:
1291:
1287:
1284:studies with
1283:
1278:
1276:
1272:
1268:
1264:
1260:
1256:
1251:
1249:
1246:
1242:
1237:
1235:
1231:
1227:
1223:
1219:
1215:
1211:
1207:
1195:
1179:
1177:Adenosine, A
1176:
1175:
1171:
1167:
1164:
1160:
1159:
1156:
1155:
1154:
1152:
1148:
1144:
1140:
1136:
1132:
1129:, when three
1128:
1124:
1120:
1116:
1112:
1108:
1104:
1094:
1091:
1088:
1085:
1084:
1080:
1076:
1073:
1069:
1066:
1062:
1059:
1055:
1054:
1051:
1049:
1045:
1041:
1037:
1033:
1032:nucleic acids
1029:
1025:
1021:
1011:
1009:
1004:
999:
995:
991:
981:
979:
975:
974:aspartic acid
971:
967:
964:
960:
956:
952:
948:
939:
937:
928:
919:
917:
913:
909:
906:, as used in
905:
901:
897:
893:
889:
888:covalent bond
884:
882:
878:
874:
870:
866:
862:
858:
854:
850:
846:
843:
839:
835:
831:
827:
823:
819:
815:
811:
810:nucleic acids
807:
804:
800:
796:
793:
787:
757:
745:
738:
733:
716:
710:
707:
704:
701:
698:
697:
693:
689:
680:
679:
675:
671:
666:
662:
654:
646:
640:
639:
635:
630:
625:
624:Heat capacity
621:
620:
615:
611:
605:
601:
598:
597:
594:
590:
586:
584:
581:
580:
576:
573:
569:
568:
564:
562:
561:Melting point
559:
558:
554:
552:
549:
548:
544:
541:
540:
536:
534:
531:
530:
509:
506:
502:
501:
496:
487:
482:
481:
478:
471:
457:
447:
446:
443:
436:
428:
424:
423:DTXSID6022557
420:
419:
417:
407:
403:
402:
395:
391:
390:
388:
386:
383:
382:
375:
374:
372:
370:
367:
366:
359:
355:
354:
352:
346:
342:
341:
334:
330:
329:
327:
325:
322:
321:
314:
310:
309:
307:
304:
300:
299:
295:
292:
288:
287:
280:
279:
277:
275:
270:
269:
265:
261:
258:
256:
254:ECHA InfoCard
251:
250:
243:
239:
238:
236:
234:
231:
230:
223:
219:
218:
216:
214:
211:
210:
203:
199:
198:
196:
194:
191:
190:
183:
179:
178:
176:
174:
171:
170:
166:
163:
159:
158:
151:
147:
144:
140:
139:
137:
133:
128:
127:
120:
116:
115:
113:
110:
106:
105:
100:
96:6-Aminopurine
92:
86:
80:
76:
71:
61:
57:
52:
48:
47:
43:
39:
34:
26:
22:
3063:Combinations
2990:Folinic acid
2949:Pyridoxamine
2920:Dexpanthenol
2869:Sulbutiamine
2849:Benfotiamine
2844:Allithiamine
2746:Menadione (K
2705:Tocofersolan
2633:Paricalcitol
2623:Calcipotriol
2613:Alfacalcidol
2609:D analogues
2559:Previtamin D
2081:Deoxyinosine
2071:Deoxyuridine
2025:
1914:Hypoxanthine
1903:
1884:constituents
1882:Nucleic acid
1802:
1798:
1784:. Retrieved
1780:
1770:
1759:. Retrieved
1755:ScienceDaily
1753:
1743:
1732:. Retrieved
1728:the original
1713:
1668:
1664:
1654:
1613:
1609:
1603:
1578:
1574:
1568:
1557:. Retrieved
1553:
1544:
1533:. Retrieved
1529:
1519:
1484:
1480:
1470:
1452:
1419:
1415:
1408:
1383:
1379:
1373:
1362:. Retrieved
1358:
1349:
1341:
1336:
1322:heterocyclic
1304:and related
1279:
1252:
1247:
1238:
1202:
1200:
1100:
1017:
1008:aqua ammonia
987:
945:
942:Biosynthesis
933:
895:
885:
830:biochemistry
798:
794:
755:
754:
673:
663:96.9 kJ/mol
652:
628:
603:
593:aqua ammonia
369:RTECS number
202:ChEMBL226345
102:Identifiers
94:Other names
84:
3128:Nucleobases
3091:from market
2902:Niacinamide
2859:Octotiamine
2680:Tocotrienol
1310:outer space
1121:. It forms
1119:deoxyribose
1028:nucleotides
1020:nucleobases
963:amino acids
916:deoxyribose
892:deoxyribose
688:median dose
674:Lethal dose
542:Appearance
498:Properties
260:100.000.724
182:CHEBI:16708
3122:Categories
2980:Folic acid
2940:Pyridoxine
2925:Pantethine
2882:Riboflavin
2755:Various (K
2653:Tocopherol
2628:Tacalcitol
2536:Ergosterol
2502:β-Carotene
2497:α-Carotene
2100:Nucleotide
2038:Wybutosine
2033:Xanthosine
1968:Nucleoside
1931:Pyrimidine
1891:Nucleobase
1795:Barbatti M
1786:2011-09-01
1761:2011-08-09
1734:2011-08-10
1559:2022-12-23
1535:2022-12-23
1364:2022-12-23
1328:References
1300:(adenine,
1286:meteorites
1265:with five
1228:(NAD) and
1222:riboflavin
1107:nucleoside
853:Coenzyme A
851:(FAD) and
832:including
583:Solubility
533:Molar mass
394:JAC85A2161
303:IUPHAR/BPS
213:ChemSpider
130:3D model (
109:CAS Number
25:Adrenaline
3101:Phase III
3089:Withdrawn
2954:Pyritinol
2834:analogues
2512:Tretinoin
2066:Thymidine
1990:Guanosine
1985:Adenosine
1444:0584-8539
1288:found on
1214:Vitamin B
1203:Vitamin B
1143:adenosine
1125:(ATP), a
1103:adenosine
990:formamide
970:glutamine
936:tautomers
922:Structure
910:and ATP;
900:Adenosine
842:cofactors
824:(C), and
645:formation
376:AU6125000
281:200-796-1
273:EC Number
21:Adenosine
3138:Vitamins
2823:Thiamine
2467:Vitamins
2230:c-di-AMP
2225:c-di-GMP
2010:Cytidine
1946:Cytosine
1919:Xanthine
1827:21804965
1705:21836052
1646:21941930
1638:11536683
1595:13731263
1511:16744538
1314:UV light
1255:Joan Oró
1137:between
1038:via two
1014:Function
822:cytosine
801:) is a
668:Hazards
233:DrugBank
31:Adenine
3133:Purines
2801:soluble
2507:Retinol
2481:soluble
2020:Inosine
2000:Uridine
1941:Thymine
1909:Guanine
1904:Adenine
1807:Bibcode
1696:3161613
1673:Bibcode
1618:Bibcode
1530:Gallica
1502:1254803
1424:Bibcode
1388:Bibcode
1302:guanine
1263:ammonia
1210:vitamin
1189:History
1036:thymine
1030:of the
1024:guanine
966:glycine
951:guanine
869:thymine
847:(NAD),
826:thymine
818:guanine
756:Adenine
737:what is
735: (
600:Acidity
589:ethanol
551:Density
345:PubChem
242:DB00173
167:608603
119:73-24-5
3084:WHO-EM
2967:Biotin
2897:Niacin
2799:Water
1936:Uracil
1899:Purine
1825:
1703:
1693:
1644:
1636:
1593:
1509:
1499:
1463:
1442:
1243:after
1218:niacin
1149:, and
1113:, and
1111:ribose
1048:uracil
972:, and
904:ribose
877:uracil
803:purine
792:symbol
732:verify
729:
702:(SDS)
477:SMILES
333:D00034
193:ChEMBL
73:Names
2699:Delta
2695:Gamma
2685:Alpha
2673:Delta
2668:Gamma
2658:Alpha
2240:cGAMP
2235:cADPR
1642:S2CID
1290:Earth
1275:Earth
1245:Greek
996:) or
820:(G),
442:InChI
296:3903
173:ChEBI
132:JSmol
2690:Beta
2663:Beta
2479:Fat
2421:dXTP
2416:dITP
2411:dCTP
2406:dUTP
2401:dTTP
2396:dGTP
2391:dATP
2358:mUTP
2322:dCDP
2317:dUDP
2312:dTDP
2307:dGDP
2302:dADP
2274:mUDP
2220:cGMP
2215:cAMP
2197:dXMP
2192:dIMP
2187:dCMP
2182:dUMP
2177:dTMP
2172:dGMP
2167:dAMP
2129:mUMP
1823:PMID
1724:NASA
1701:PMID
1634:PMID
1591:PMID
1507:PMID
1440:ISSN
1296:and
1282:NASA
1248:ἀδήν
1220:and
1105:, a
863:and
706:MSDS
385:UNII
324:KEGG
313:4788
2471:A11
2378:XTP
2373:ITP
2368:CTP
2363:UTP
2353:GTP
2348:ATP
2284:CDP
2279:UDP
2269:GDP
2264:ADP
2149:XMP
2144:IMP
2139:CMP
2134:UMP
2124:GMP
2119:AMP
1815:doi
1691:PMC
1681:doi
1669:108
1626:doi
1583:doi
1497:PMC
1489:doi
1432:doi
1396:doi
1298:RNA
1294:DNA
1273:on
1261:of
908:RNA
881:RNA
879:in
875:or
873:DNA
871:in
865:RNA
861:DNA
814:DNA
812:of
799:Ade
797:or
790:) (
656:298
411:EPA
358:190
348:CID
222:185
23:or
3124::
3097::
3004:12
2942:,
1821:.
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1803:13
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1418:.
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1153:.
1145:,
1050:.
980:.
968:,
883:.
684:50
682:LD
648:(Δ
609:)
602:(p
3037:C
3002:B
2975:9
2973:B
2962:7
2960:B
2934:6
2932:B
2910:5
2908:B
2891:3
2889:B
2877:2
2875:B
2832:1
2830:B
2818:1
2816:B
2809:B
2786:)
2784:7
2777:)
2775:6
2768:)
2766:5
2759:)
2757:4
2750:)
2748:3
2741:)
2739:2
2732:)
2730:1
2715:K
2645:E
2604:5
2602:D
2590:4
2588:D
2561:3
2549:3
2547:D
2531:2
2529:D
2522:D
2489:A
2473:)
2469:(
2459:e
2452:t
2445:v
2026:N
1874:e
1867:t
1860:v
1829:.
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1398::
1390::
1384:4
1367:.
1205:4
795:A
786:/
783:n
780:ɪ
777:n
774:ɪ
771:d
768:æ
765:ˈ
762:/
758:(
727:Y
690:)
686:(
658:)
653:H
650:f
631:)
629:C
627:(
607:a
604:K
526:5
523:N
520:5
517:H
514:5
511:C
413:)
409:(
134:)
85:H
83:9
27:.
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