24:
264:
545:
384:
111:
287:
InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1
297:
InChI=1/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1
739:
Danenberg, Peter V.; Gustavsson, Bengt; Johnston, Patrick; Lindberg, Per; Moser, Rudolf; Odin, Elisabeth; Peters, Godefridus J.; Petrelli, Nicholas (2016-10-01).
541:) to achieve necessary activation. The active metabolite is being evaluated in clinical trials for patients with colorectal cancer in combination with 5-FU.
397:
392:
313:
1013:
876:
872:
805:
645:
1843:
188:
454:
1217:
868:
864:
278:
1860:
404:
1532:
659:
Födinger M, Hörl WH, Sunder-Plassmann G (2000). "Molecular biology of 5,10-methylenetetrahydrofolate reductase".
462:
798:
990:
626:
533:-5,10-methylene-THF is a biomodulator that has proven to enhance the desired cytotoxic antitumor effect of
221:
1541:
1523:
854:
589:
565:
242:
151:
557:
522:
502:
791:
605:
593:
569:
259:
1354:
1085:
447:
443:
439:
182:
1848:
1098:
817:
609:
506:
1210:
998:
840:
1008:
1003:
850:
36:
1809:
1589:
1313:
916:
549:
498:
230:
171:
87:
8:
1703:
1090:
896:
597:
77:
263:
131:
1892:
1482:
1377:
1112:
741:"Folates as adjuvants to anticancer agents: Chemical rationale and mechanism of action"
716:
687:
1769:
1744:
1203:
1183:
942:
924:
770:
762:
757:
740:
721:
707:
668:
23:
1887:
1779:
1754:
1674:
752:
711:
703:
613:
458:
336:
210:
1454:
1449:
1444:
1784:
1341:
1326:
946:
577:
428:
1432:
1427:
1422:
1417:
688:"Formaldehyde-detoxifying role of the tetrahydromethanopterin-linked pathway in
1854:
1774:
1487:
1300:
962:
537:(5-FU) and can bypass the metabolic pathway required by other folates (such as
375:
1881:
1623:
1613:
1598:
1318:
1075:
1028:
980:
766:
573:
478:
Methylenetetrahydrofolate is a source of the equivalent of formaldehyde or CH
1261:
1256:
427:) is cofactor in several biochemical reactions. It exists in nature as the
1829:
1749:
1708:
1661:
1628:
1608:
1603:
1464:
1392:
1382:
1372:
1230:
1080:
1070:
1038:
774:
725:
685:
672:
538:
534:
514:
486:
485:
Methylenetetrahydrofolate is also an intermediate in the detoxification of
1761:
1618:
1439:
1331:
1065:
1018:
548:
MTHFR metabolism: folate cycle, methionine cycle, trans-sulfuration and
1699:
1691:
1684:
1648:
1641:
1568:
1514:
1496:
1412:
1387:
1361:
1336:
1295:
1145:
1033:
1023:
886:
363:
162:
1804:
1796:
1713:
1679:
1505:
1474:
1404:
1281:
1271:
1248:
1140:
1135:
970:
956:
518:
374:
Except where otherwise noted, data are given for materials in their
1582:
783:
738:
544:
510:
646:"Entrez Gene: MTHFR methylenetetrahydrofolate reductase (NAD(P)H)"
110:
1266:
1226:
1195:
1176:
1120:
832:
321:
O=C(O)(NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)/N=C(/N)NC=2NC3)C4)CCC(=O)O
197:
1739:
1726:
1656:
1150:
1125:
1059:
1055:
1051:
1047:
906:
814:
553:
451:
142:
601:
122:
100:
658:
556:: 5-methyltetrahydrofolate; 5,10-methylenetetrahydrofolate;
247:
1155:
1130:
1043:
585:
581:
561:
521:
and is the C1-donor in the reactions catalyzed by TS and
686:
Marx, C. J.; Chistoserdova, L.; Lidstrom, M. E. (2003).
501:, for methylation of 2-deoxy-uridine-5-monophosphate (
434:
As an intermediate in one-carbon metabolism, 5,10-CH
457:(MTHFR) It is mainly produced by the reaction of
1879:
209:
86:
1211:
799:
564:: betaine-homocysteine S-methyltransferase;
652:
1337:Calcitriol (1,25-dihydroxycholecalciferol)
1218:
1204:
806:
792:
492:
473:
262:
170:
756:
715:
421:N5,N10-Methylenetetrahydrofolate; 5,10-CH
229:
543:
505:) to 2-deoxy-thymidine-5-monophosphate (
745:Critical Reviews in Oncology/Hematology
604:: methylenetetrahydrofolate reductase;
446:, and methenyltetrahydrofolate. It is
258:
187:
1880:
1199:
787:
638:
468:
461:with serine, catalyzed by the enzyme
290:Key: QYNUQALWYRSVHF-ABLWVSNPSA-N
150:
130:
813:
455:methylenetetrahydrofolate reductase
300:Key: QYNUQALWYRSVHF-ABLWVSNPBB
200:
13:
1533:2-Methylnaphthalene-1,4-diamine (K
1225:
14:
1904:
758:10.1016/j.critrevonc.2016.08.001
708:10.1128/jb.185.23.7160-7168.2003
382:
22:
568:: cystathionine beta synthase;
528:
497:It is the one-carbon donor for
463:serine hydroxymethyltransferase
378:(at 25 °C , 100 kPa).
17:5,10-Methylenetetrahydrofolate
1542:4-Amino-3-methyl-1-naphthol (K
1524:4-Amino-2-methyl-1-naphthol (K
732:
679:
592:flavine adenine dicucleotide;
588:: deoxyuridine monophosphate;
576:: dihydrofolate (vitamin B9);
560:: Bcl-2-associated X protein;
417:5,10-Methylenetetrahydrofolate
189:5,10-methylenetetrahydrofolate
1:
632:
627:5,10-Methenyltetrahydrofolate
608:: S-adenosyl-L-homocysteine;
596:: 10-formyltetrahydrofolate;
572:: cystathionine gamma-lyase;
7:
690:Methylobacterium extorquens
620:
612:: S-adenosyl-L-methionine;
584:: thymidine monophosphate;
10:
1909:
523:thymidylate synthase (FAD)
368:457.44 g/mol
1838:
1822:
1795:
1567:
1558:
1473:
1403:
1332:25-hydroxycholecalciferol
1280:
1247:
1238:
1168:
1111:
989:
831:
824:
372:
329:
309:
274:
70:
56:
35:
30:
21:
444:5-formyltetrahydrofolate
440:5-methyltetrahydrofolate
600:: methionine synthase;
493:Pyrimidine biosynthesis
474:Formaldehyde equivalent
617:
1355:Dihydroergocalciferol
547:
513:is necessary for the
431:-5,10-methylene-THF.
1810:Dehydroascorbic acid
1314:7-Dehydrocholesterol
550:hyperhomocysteinemia
499:thymidylate synthase
1704:Pyridoxal phosphate
616:: tetrahydrofolate.
580:: dimethylglycine;
18:
1865:Never to phase III
1378:Dihydrotachysterol
618:
469:Selected functions
405:Infobox references
16:
1875:
1874:
1818:
1817:
1770:Adenosylcobalamin
1745:Dihydrofolic acid
1554:
1553:
1193:
1192:
1164:
1163:
482:in biosyntheses.
438:-THF converts to
413:Chemical compound
411:
410:
243:CompTox Dashboard
112:Interactive image
50:
1900:
1780:Hydroxocobalamin
1755:Levomefolic acid
1675:Pantothenic acid
1565:
1564:
1488:Phylloquinone (K
1245:
1244:
1220:
1213:
1206:
1197:
1196:
829:
828:
808:
801:
794:
785:
784:
779:
778:
760:
736:
730:
729:
719:
683:
677:
676:
656:
650:
649:
642:
459:tetrahydrofolate
395:
389:
386:
385:
337:Chemical formula
267:
266:
251:
249:
233:
213:
202:
191:
174:
154:
134:
114:
90:
48:
26:
19:
15:
1908:
1907:
1903:
1902:
1901:
1899:
1898:
1897:
1878:
1877:
1876:
1871:
1870:
1855:Clinical trials
1834:
1814:
1791:
1785:Methylcobalamin
1765:
1736:
1723:
1695:
1671:
1652:
1638:
1593:
1579:
1560:
1550:
1545:
1536:
1527:
1518:
1509:
1500:
1497:Menaquinones (K
1491:
1469:
1399:
1365:
1351:
1342:Calcitroic acid
1327:Cholecalciferol
1322:
1310:
1292:
1276:
1240:
1234:
1224:
1194:
1189:
1160:
1107:
1102:
1094:
985:
976:
968:
952:
938:
928:
920:
912:
902:
892:
882:
860:
846:
820:
812:
782:
737:
733:
684:
680:
657:
653:
644:
643:
639:
635:
623:
531:
495:
481:
476:
471:
437:
429:diastereoisomer
424:
414:
407:
402:
401:
400: ?)
391:
387:
383:
379:
357:
353:
349:
345:
339:
325:
322:
317:
316:
305:
302:
301:
298:
292:
291:
288:
282:
281:
270:
252:
245:
236:
216:
203:
177:
157:
137:
117:
104:
93:
80:
66:
64:
62:
52:
12:
11:
5:
1906:
1896:
1895:
1890:
1873:
1872:
1869:
1868:
1867:
1866:
1863:
1852:
1846:
1840:
1839:
1836:
1835:
1833:
1832:
1826:
1824:
1820:
1819:
1816:
1815:
1813:
1812:
1807:
1801:
1799:
1793:
1792:
1790:
1789:
1788:
1787:
1782:
1777:
1775:Cyanocobalamin
1772:
1763:
1759:
1758:
1757:
1752:
1747:
1742:
1734:
1731:
1730:
1729:
1721:
1718:
1717:
1716:
1711:
1706:
1693:
1689:
1688:
1687:
1682:
1677:
1669:
1666:
1665:
1664:
1659:
1650:
1646:
1645:
1644:
1636:
1633:
1632:
1631:
1626:
1621:
1616:
1611:
1606:
1601:
1591:
1587:
1586:
1585:
1577:
1573:
1571:
1562:
1556:
1555:
1552:
1551:
1549:
1548:
1543:
1539:
1534:
1530:
1525:
1521:
1516:
1512:
1507:
1503:
1498:
1494:
1489:
1485:
1483:Naphthoquinone
1479:
1477:
1471:
1470:
1468:
1467:
1462:
1461:
1460:
1457:
1452:
1447:
1437:
1436:
1435:
1430:
1425:
1420:
1409:
1407:
1401:
1400:
1398:
1397:
1396:
1395:
1390:
1385:
1380:
1375:
1367:
1363:
1359:
1358:
1357:
1349:
1346:
1345:
1344:
1339:
1334:
1329:
1324:
1320:
1316:
1308:
1305:
1304:
1303:
1301:Ergocalciferol
1298:
1290:
1286:
1284:
1278:
1277:
1275:
1274:
1269:
1264:
1259:
1253:
1251:
1242:
1236:
1235:
1223:
1222:
1215:
1208:
1200:
1191:
1190:
1188:
1187:
1172:
1170:
1166:
1165:
1162:
1161:
1159:
1158:
1153:
1148:
1143:
1138:
1133:
1128:
1123:
1117:
1115:
1109:
1108:
1106:
1105:
1100:
1096:
1092:
1088:
1083:
1078:
1073:
1068:
1063:
1041:
1036:
1031:
1026:
1021:
1016:
1011:
1006:
1001:
995:
993:
987:
986:
984:
983:
978:
974:
966:
960:
954:
950:
940:
936:
926:
918:
914:
910:
904:
900:
894:
890:
884:
880:
862:
858:
848:
844:
837:
835:
826:
822:
821:
811:
810:
803:
796:
788:
781:
780:
731:
702:(24): 7160–8.
678:
651:
636:
634:
631:
630:
629:
622:
619:
530:
527:
494:
491:
479:
475:
472:
470:
467:
435:
422:
412:
409:
408:
403:
381:
380:
376:standard state
373:
370:
369:
366:
360:
359:
355:
351:
347:
343:
340:
335:
332:
331:
327:
326:
324:
323:
320:
312:
311:
310:
307:
306:
304:
303:
299:
296:
295:
293:
289:
286:
285:
277:
276:
275:
272:
271:
269:
268:
260:DTXSID90955873
255:
253:
241:
238:
237:
235:
234:
226:
224:
218:
217:
215:
214:
206:
204:
196:
193:
192:
185:
179:
178:
176:
175:
167:
165:
159:
158:
156:
155:
147:
145:
139:
138:
136:
135:
127:
125:
119:
118:
116:
115:
107:
105:
98:
95:
94:
92:
91:
83:
81:
76:
73:
72:
68:
67:
60:
58:
54:
53:
51:-glutamic acid
47:)-yl)benzoyl]-
39:
33:
32:
28:
27:
9:
6:
4:
3:
2:
1905:
1894:
1891:
1889:
1886:
1885:
1883:
1864:
1862:
1859:
1858:
1856:
1853:
1850:
1847:
1845:
1842:
1841:
1837:
1831:
1830:Multivitamins
1828:
1827:
1825:
1821:
1811:
1808:
1806:
1805:Ascorbic acid
1803:
1802:
1800:
1798:
1794:
1786:
1783:
1781:
1778:
1776:
1773:
1771:
1768:
1767:
1766:
1760:
1756:
1753:
1751:
1748:
1746:
1743:
1741:
1738:
1737:
1732:
1728:
1725:
1724:
1719:
1715:
1712:
1710:
1707:
1705:
1701:
1698:
1697:
1696:
1690:
1686:
1683:
1681:
1678:
1676:
1673:
1672:
1667:
1663:
1660:
1658:
1655:
1654:
1653:
1647:
1643:
1640:
1639:
1634:
1630:
1627:
1625:
1624:Prosultiamine
1622:
1620:
1617:
1615:
1614:Fursultiamine
1612:
1610:
1607:
1605:
1602:
1600:
1599:Acefurtiamine
1597:
1596:
1595:
1588:
1584:
1581:
1580:
1575:
1574:
1572:
1570:
1566:
1563:
1557:
1547:
1540:
1538:
1531:
1529:
1522:
1520:
1513:
1511:
1504:
1502:
1495:
1493:
1486:
1484:
1481:
1480:
1478:
1476:
1472:
1466:
1463:
1458:
1456:
1453:
1451:
1448:
1446:
1443:
1442:
1441:
1438:
1434:
1431:
1429:
1426:
1424:
1421:
1419:
1416:
1415:
1414:
1411:
1410:
1408:
1406:
1402:
1394:
1391:
1389:
1386:
1384:
1381:
1379:
1376:
1374:
1371:
1370:
1368:
1366:
1360:
1356:
1353:
1352:
1347:
1343:
1340:
1338:
1335:
1333:
1330:
1328:
1325:
1323:
1317:
1315:
1312:
1311:
1306:
1302:
1299:
1297:
1294:
1293:
1288:
1287:
1285:
1283:
1279:
1273:
1270:
1268:
1265:
1263:
1260:
1258:
1255:
1254:
1252:
1250:
1246:
1243:
1237:
1232:
1228:
1221:
1216:
1214:
1209:
1207:
1202:
1201:
1198:
1186:
1185:
1179:
1178:
1174:
1173:
1171:
1167:
1157:
1154:
1152:
1149:
1147:
1144:
1142:
1139:
1137:
1134:
1132:
1129:
1127:
1124:
1122:
1119:
1118:
1116:
1114:
1110:
1104:
1097:
1095:
1089:
1087:
1084:
1082:
1079:
1077:
1076:Molybdopterin
1074:
1072:
1069:
1067:
1064:
1061:
1057:
1053:
1049:
1045:
1042:
1040:
1037:
1035:
1032:
1030:
1029:Cofactor F430
1027:
1025:
1022:
1020:
1017:
1015:
1012:
1010:
1007:
1005:
1002:
1000:
997:
996:
994:
992:
988:
982:
981:Coenzyme F420
979:
972:
964:
963:Phylloquinone
961:
958:
957:Ascorbic acid
955:
948:
944:
941:
934:
930:
922:
915:
908:
905:
898:
895:
888:
885:
878:
874:
870:
866:
863:
856:
852:
849:
842:
839:
838:
836:
834:
830:
827:
823:
819:
816:
809:
804:
802:
797:
795:
790:
789:
786:
776:
772:
768:
764:
759:
754:
750:
746:
742:
735:
727:
723:
718:
713:
709:
705:
701:
697:
693:
691:
682:
674:
670:
666:
662:
655:
647:
641:
637:
628:
625:
624:
615:
611:
607:
603:
599:
595:
591:
587:
583:
579:
575:
571:
567:
563:
559:
555:
551:
546:
542:
540:
536:
526:
524:
520:
516:
512:
508:
504:
500:
490:
488:
483:
466:
464:
460:
456:
453:
449:
445:
441:
432:
430:
426:
418:
406:
399:
394:
377:
371:
367:
365:
362:
361:
341:
338:
334:
333:
328:
319:
318:
315:
308:
294:
284:
283:
280:
273:
265:
261:
257:
256:
254:
244:
240:
239:
232:
228:
227:
225:
223:
220:
219:
212:
208:
207:
205:
199:
195:
194:
190:
186:
184:
181:
180:
173:
169:
168:
166:
164:
161:
160:
153:
149:
148:
146:
144:
141:
140:
133:
129:
128:
126:
124:
121:
120:
113:
109:
108:
106:
102:
97:
96:
89:
85:
84:
82:
79:
75:
74:
69:
55:
46:
43:-pteridin-8(9
42:
38:
34:
29:
25:
20:
1823:Combinations
1750:Folinic acid
1709:Pyridoxamine
1680:Dexpanthenol
1629:Sulbutiamine
1609:Benfotiamine
1604:Allithiamine
1506:Menadione (K
1465:Tocofersolan
1393:Paricalcitol
1383:Calcipotriol
1373:Alfacalcidol
1369:D analogues
1319:Previtamin D
1181:
1175:
1081:Mycofactocin
1071:Methanofuran
991:non-vitamins
932:
825:Active forms
748:
744:
734:
699:
696:J. Bacteriol
695:
689:
681:
667:(1): 20–33.
664:
660:
654:
640:
535:Fluorouracil
532:
529:Biomodulator
515:biosynthesis
496:
487:formaldehyde
484:
477:
433:
420:
416:
415:
152:ChEMBL117348
71:Identifiers
57:Other names
44:
40:
1851:from market
1662:Niacinamide
1619:Octotiamine
1440:Tocotrienol
1066:Lipoic Acid
1044:Heme / Haem
971:Menaquinone
751:: 118–131.
330:Properties
132:CHEBI:20502
1882:Categories
1740:Folic acid
1700:Pyridoxine
1685:Pantethine
1642:Riboflavin
1515:Various (K
1413:Tocopherol
1388:Tacalcitol
1296:Ergosterol
1262:β-Carotene
1257:α-Carotene
1169:Base forms
1113:metal ions
1039:Coenzyme Q
1034:Coenzyme M
1024:Coenzyme B
887:Coenzyme A
841:TPP / ThDP
633:References
539:leucovorin
364:Molar mass
231:0SXY5ET48B
163:ChemSpider
99:3D model (
78:CAS Number
37:IUPAC name
1893:Coenzymes
1861:Phase III
1849:Withdrawn
1714:Pyritinol
1594:analogues
1272:Tretinoin
1099:THMPT / H
897:PLP / P5P
818:cofactors
767:1879-0461
661:J Nephrol
519:thymidine
448:substrate
88:3432-99-3
1583:Thiamine
1227:Vitamins
1184:vitamins
1177:vitamins
1091:THB / BH
925:DHFA / H
917:THFA / H
833:vitamins
775:27637357
726:14645276
673:10720211
621:See also
511:coenzyme
450:for the
1888:Folates
1561:soluble
1267:Retinol
1241:soluble
509:). The
398:what is
396: (
358:
198:PubChem
59:5,10-CH
1844:WHO-EM
1727:Biotin
1657:Niacin
1559:Water
1131:Fe, Fe
943:AdoCbl
907:Biotin
815:Enzyme
773:
765:
724:
717:296243
714:
671:
554:5-MTHF
452:enzyme
393:verify
390:
314:SMILES
211:108194
143:ChEMBL
31:Names
1459:Delta
1455:Gamma
1445:Alpha
1433:Delta
1428:Gamma
1418:Alpha
947:MeCbl
877:NADPH
602:MTHFR
279:InChI
172:97272
123:ChEBI
101:JSmol
63:-THF,
1450:Beta
1423:Beta
1239:Fat
1182:see
1014:PAPS
1009:SAMe
933:MTHF
873:NADP
869:NADH
771:PMID
763:ISSN
722:PMID
692:AM1"
669:PMID
610:SAME
594:FTHF
586:dUMP
582:dTMP
562:BHMT
507:dTMP
503:dUMP
425:-THF
222:UNII
183:MeSH
65:MTHF
1231:A11
1103:MPT
1086:PQQ
1019:GSH
1004:CTP
999:ATP
969:),
959:(C)
865:NAD
855:FAD
851:FMN
753:doi
749:106
712:PMC
704:doi
700:185
614:THF
606:SAH
590:FAD
578:DMG
574:DHF
570:CGL
566:CBS
558:BAX
517:of
248:EPA
201:CID
1884::
1857::
1764:12
1702:,
1180::
1156:Zn
1151:Ni
1146:Mo
1141:Mn
1136:Mg
1126:Cu
1121:Ca
1058:,
1054:,
1050:,
973:(K
965:(K
951:12
949:(B
945:,
935:(B
931:,
929:FA
923:,
921:FA
909:(B
899:(B
889:(B
879:(B
875:,
871:,
867:,
857:(B
853:,
843:(B
769:.
761:.
747:.
743:.
720:.
710:.
698:.
694:.
665:13
663:.
598:MS
552:.
525:.
489:.
465:.
442:,
348:23
344:20
1797:C
1762:B
1735:9
1733:B
1722:7
1720:B
1694:6
1692:B
1670:5
1668:B
1651:3
1649:B
1637:2
1635:B
1592:1
1590:B
1578:1
1576:B
1569:B
1546:)
1544:7
1537:)
1535:6
1528:)
1526:5
1519:)
1517:4
1510:)
1508:3
1501:)
1499:2
1492:)
1490:1
1475:K
1405:E
1364:5
1362:D
1350:4
1348:D
1321:3
1309:3
1307:D
1291:2
1289:D
1282:D
1249:A
1233:)
1229:(
1219:e
1212:t
1205:v
1101:4
1093:4
1062:)
1060:O
1056:C
1052:B
1048:A
1046:(
977:)
975:2
967:1
953:)
939:)
937:9
927:2
919:4
913:)
911:7
903:)
901:6
893:)
891:5
883:)
881:3
861:)
859:2
847:)
845:1
807:e
800:t
793:v
777:.
755::
728:.
706::
675:.
648:.
480:2
436:2
423:2
419:(
388:N
356:6
354:O
352:7
350:N
346:H
342:C
250:)
246:(
103:)
61:2
49:L
45:H
41:N
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