Marvin 11161213262D 59 65 0 0 0 0 999 V2000 8.0121 -0.3989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0121 -1.2260 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7264 -1.6374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7264 0.0167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4407 -0.3989 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4420 -1.2260 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1553 -1.6354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8686 -1.2237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1526 0.0186 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8650 -0.3956 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8649 1.2538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1487 0.8422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5814 0.8397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5721 0.0177 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.2799 -0.3984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9942 0.0059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2942 1.2456 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.9994 0.8297 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7115 1.2267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7219 2.0455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0166 2.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2968 2.0624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2984 -1.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4334 0.4281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8630 0.4322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2883 0.4197 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7096 0.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3072 -2.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1342 -2.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7111 -0.4072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4263 0.8303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6000 3.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4270 3.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4375 -2.0488 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1482 -0.8062 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5694 -0.8062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2792 -1.2257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2764 -2.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9863 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5556 -2.4601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9835 -3.2949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6933 -3.7144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6866 -4.5343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3995 -4.9537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1175 -4.5461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1211 -3.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4075 -3.3033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8321 -4.9644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5856 -1.2243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8677 -1.6370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5865 -0.3973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1507 -1.2227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1517 -0.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8706 0.0156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8720 0.8416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1543 1.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4376 0.8387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4407 0.0144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1539 2.0797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11 12 1 0 0 0 0 3 28 1 0 0 0 0 13 14 1 0 0 0 0 3 29 1 0 0 0 0 1 2 1 0 0 0 0 27 30 2 0 0 0 0 1 4 1 0 0 0 0 27 31 1 0 0 0 0 2 3 1 0 0 0 0 21 32 1 0 0 0 0 5 9 1 0 0 0 0 21 33 1 0 0 0 0 13 17 1 0 0 0 0 6 34 1 6 0 0 0 14 15 1 0 0 0 0 9 35 1 6 0 0 0 15 16 1 0 0 0 0 14 36 1 6 0 0 0 16 18 1 0 0 0 0 36 37 1 0 0 0 0 17 18 1 0 0 0 0 37 38 1 0 0 0 0 6 7 1 0 0 0 0 38 39 1 0 0 0 0 7 8 1 0 0 0 0 38 40 2 0 0 0 0 8 10 1 0 0 0 0 39 41 2 0 0 0 0 9 10 1 0 0 0 0 41 42 1 0 0 0 0 3 6 1 0 0 0 0 42 43 2 0 0 0 0 5 4 1 0 0 0 0 43 44 1 0 0 0 0 17 22 1 0 0 0 0 44 45 2 0 0 0 0 18 19 1 0 0 0 0 45 46 1 0 0 0 0 19 20 1 0 0 0 0 46 47 2 0 0 0 0 47 42 1 0 0 0 0 20 21 1 0 0 0 0 45 48 1 0 0 0 0 21 22 1 0 0 0 0 23 49 1 0 0 0 0 5 6 1 0 0 0 0 49 50 1 0 0 0 0 2 23 1 1 0 0 0 49 51 2 0 0 0 0 50 52 2 0 0 0 0 5 24 1 1 0 0 0 52 53 1 0 0 0 0 9 12 1 0 0 0 0 53 54 2 0 0 0 0 10 25 1 1 0 0 0 54 55 1 0 0 0 0 10 14 1 0 0 0 0 55 56 2 0 0 0 0 17 26 1 1 0 0 0 56 57 1 0 0 0 0 13 11 2 0 0 0 0 57 58 2 0 0 0 0 58 53 1 0 0 0 0 18 27 1 1 0 0 0 56 59 1 0 0 0 0 M END > CHEBI:65456 > asprellic acid C > A pentacyclic triterpenoid that is the diester obtained by the global condensation of the hydroxy groups of (3β)-3,27-dihydroxyolean-12-en-28-oic acid with trans-4-coumaric acid and cis-4-coumaric acid respectively. It is isolated from the dried leaves of Ilex asprella and exhibits significant toxicity against KB (epidermoid carcinoma of the nasopharynx) and RPMI-7951 (melanoma) cell lines. > 3 > 3-O-cis-p-coumaroyl-27-O-trans-p-coumaroyl-3beta,27-dihydroxy-olean-12-en-28-oic acid > (3beta)-27-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}olean-12-en-28-oic acid > C48H60O8 > 764.98520 > 764.42882 > 0 > [H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(COC(=O)\C=C\c3ccc(O)cc3)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](OC(=O)\C=C/c4ccc(O)cc4)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O > InChI=1S/C48H60O8/c1-43(2)25-26-47(42(53)54)27-28-48(30-55-40(51)19-11-31-7-13-33(49)14-8-31)35(36(47)29-43)17-18-38-45(5)23-22-39(44(3,4)37(45)21-24-46(38,48)6)56-41(52)20-12-32-9-15-34(50)16-10-32/h7-17,19-20,36-39,49-50H,18,21-30H2,1-6H3,(H,53,54)/b19-11+,20-12-/t36-,37-,38+,39-,45-,46+,47-,48-/m0/s1 > YBOIBOWMTWFCEG-AINGNVPBSA-N > 8133297 $$$$