NPASS Compound

Natural Product: NPC470450

Natural Product ID	NPC470450
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Geniculatin
IUPAC Name	n.a.
Synonyms	Geniculatin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037053
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 146156 0 0 0 0 0 0 0 0999 V2000 -14.4880 4.1080 -1.8717 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9664 2.9691 -2.5584 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2611 1.9868 -1.8454 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9400 0.9052 -1.2938 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.3272 0.8226 -1.4664 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2467 -0.0554 -0.5952 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8601 0.0224 -0.4199 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2091 1.1022 -0.9742 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8982 2.0643 -1.6727 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1964 3.1319 -2.2122 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8366 1.1672 -0.7918 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2472 2.1580 -1.2966 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1655 0.1747 -0.0785 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8966 -0.8586 0.4388 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2104 -0.8782 0.2371 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3841 -1.9685 1.2057 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1718 -3.0805 1.4024 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8010 -4.1658 2.1650 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5509 -4.1346 2.7740 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7513 -3.0554 2.6011 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1623 -1.9643 1.8166 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1932 -5.2387 3.5391 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8214 0.2952 0.0482 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8365 -0.2928 -0.8377 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7463 -0.5949 -0.1367 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4825 -0.2822 -0.4469 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1386 1.1220 -0.0540 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7686 1.4499 -0.2627 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8158 0.8340 0.5364 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2358 0.0073 1.3911 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3813 1.0882 0.4637 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4953 0.4532 -0.5568 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1674 0.0836 -1.8070 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3516 1.0673 -2.7913 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9151 0.7662 -4.0114 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3262 -0.5110 -4.3300 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1438 -1.4695 -3.3633 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5727 -1.1768 -2.1174 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8981 -0.8206 -5.5684 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8611 -0.5755 0.4356 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3764 0.3146 1.5331 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2796 1.1084 2.3251 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5175 0.7722 3.6662 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3528 1.5156 4.4687 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9967 2.6339 3.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7900 2.9889 2.6871 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9358 2.2202 1.8856 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8485 3.4005 4.7770 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2446 -1.0822 0.5069 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0729 -0.6913 -0.3365 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6170 -1.9641 1.4768 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8389 -2.5137 1.6668 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0126 -1.6196 1.9069 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3572 -0.7988 0.8489 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6299 -0.2952 1.0760 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2176 0.1045 -0.1502 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5878 0.0591 -0.2803 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2890 -1.0713 -0.5464 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6227 -0.9640 -0.6275 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2531 0.1612 -0.4688 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5999 1.3355 -0.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2316 1.2967 -0.1076 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6063 2.3537 0.1232 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2796 2.5377 -0.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5652 3.7057 0.2250 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6479 2.5948 -0.1285 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3360 1.4094 -0.3949 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6419 0.2344 -0.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7197 1.4418 -0.4915 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3503 3.7832 0.0362 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5752 4.5478 -1.1345 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6649 -2.3582 -0.7404 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4860 -3.4867 -0.6296 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0442 -4.7613 -0.8532 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7106 -4.9946 -1.2130 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9099 -3.9122 -1.3231 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3715 -2.6111 -1.0928 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2164 -6.2653 -1.4488 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5587 0.6999 2.1731 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0735 -0.0862 3.4270 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7266 -0.6370 3.0512 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1265 -1.2201 4.1318 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 0.8248 4.4425 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7978 1.2143 2.5817 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2197 -0.3741 -1.9495 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3473 0.1177 -2.7671 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5913 0.5365 -2.0501 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6409 0.3194 -3.0027 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8970 1.2470 -3.5108 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1116 -1.7687 -2.1895 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.5344 4.2989 -2.1908 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8456 4.9663 -2.1782 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4526 3.9758 -0.7769 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.6964 0.5550 -2.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7715 -0.9051 -0.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7134 3.0341 -3.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1658 -3.1540 0.9427 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4626 -5.0054 2.2780 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7708 -3.0320 3.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4765 -1.1546 1.7709 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4705 -6.1733 3.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4009 -1.2294 -1.1963 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7974 -1.0052 0.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3881 1.2358 1.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7805 1.8639 -0.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1322 2.1971 0.5860 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3627 1.1419 -0.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0319 2.0816 -2.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0548 1.5310 -4.7681 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4471 -2.4963 -3.5512 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4546 -1.9756 -1.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8098 -0.1410 -6.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1886 -1.4833 0.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2938 -0.3054 2.2126 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0384 -0.0913 4.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5634 1.2889 5.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2717 3.8542 2.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8217 2.5642 0.8961 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8330 4.4181 4.6183 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1286 -3.2156 0.8214 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7534 -3.2408 2.5374 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8969 -2.2091 2.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2842 -1.1559 1.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0514 4.2276 -0.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1477 -0.6984 -0.7682 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2599 1.9238 0.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7241 5.2580 -1.2271 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5424 5.0437 -1.0181 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6506 3.8488 -2.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5306 -3.3478 -0.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6678 -5.6496 -0.7713 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8650 -4.0527 -1.5994 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6912 -1.8094 -1.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2575 -7.0085 -0.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8136 1.4783 1.9923 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8137 -0.8813 3.6435 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1657 0.2530 2.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2844 -1.6692 3.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1877 0.6253 5.0766 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6023 2.0407 3.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2511 0.0820 -2.1664 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6391 -0.6554 -3.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6296 1.6137 -1.8087 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3274 0.5471 -3.8937 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1203 1.1623 -4.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6565 -2.0253 -2.9761 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 8 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 19 22 1 0 13 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 32 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 45 48 1 0 40 49 1 0 49 50 2 0 49 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 2 0 58 59 1 0 59 60 1 0 60 61 2 0 61 62 1 0 62 63 2 0 61 64 1 0 64 65 1 0 64 66 2 0 66 67 1 0 67 68 2 0 67 69 1 0 66 70 1 0 70 71 1 0 58 72 1 0 72 73 2 0 73 74 1 0 74 75 2 0 75 76 1 0 76 77 2 0 75 78 1 0 55 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 80 83 1 0 79 84 1 0 26 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 86 89 1 0 85 90 1 0 9 3 1 0 21 16 1 0 87 24 1 0 15 7 1 0 41 31 1 0 47 42 1 0 81 53 1 0 38 33 1 0 62 57 1 0 77 72 1 0 68 60 1 0 1 91 1 0 1 92 1 0 1 93 1 0 5 94 1 0 6 95 1 0 10 96 1 0 17 97 1 0 18 98 1 0 20 99 1 0 21100 1 0 22101 1 0 24102 1 6 26103 1 1 27104 1 0 27105 1 0 31106 1 1 32107 1 6 34108 1 0 35109 1 0 37110 1 0 38111 1 0 39112 1 0 40113 1 6 41114 1 1 43115 1 0 44116 1 0 46117 1 0 47118 1 0 48119 1 0 52120 1 0 52121 1 0 53122 1 1 55123 1 1 65124 1 0 68125 1 0 69126 1 0 71127 1 0 71128 1 0 71129 1 0 73130 1 0 74131 1 0 76132 1 0 77133 1 0 78134 1 0 79135 1 6 80136 1 1 81137 1 6 82138 1 0 83139 1 0 84140 1 0 85141 1 1 86142 1 6 87143 1 1 88144 1 0 89145 1 0 90146 1 0 M END

Standard InCHIKey	NNBOPQPMWAVYCT-JCCQZUOPSA-N
Standard InCHI	InChI=1S/C62H56O28/c1-81-55-31(67)19-33-39(45(55)71)47(73)57(53(85-33)25-7-15-29(65)16-8-25)89-61-51(77)49(75)43(69)35(87-61)21-83-59(79)41-37(23-3-11-27(63)12-4-23)42(38(41)24-5-13-28(64)14-6-24)60(80)84-22-36-44(70)50(76)52(78)62(88-36)90-58-48(74)40-34(20-32(68)56(82-2)46(40)72)86-54(58)26-9-17-30(66)18-10-26/h3-20,35-38,41-44,49-52,61-72,75-78H,21-22H2,1-2H3/t35-,36-,37-,38-,41-,42-,43-,44-,49+,50+,51-,52-,61+,62+/m1/s1
SMILES	COc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(cc1)O)O[C@@H]1O[C@H](COC(=O)[C@@H]2[C@H](c3ccc(cc3)O)[C@H]([C@H]2c2ccc(cc2)O)C(=O)OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)c(c(c4)O)OC)c3ccc(cc3)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1248.3	Volume:	1169.638 ? Van der Waals volume.
Dense:	1.067	LogP:	1.76 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.566 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.673 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	66.0
TPSA:	451.62 ? Topological Polar Surface Area.	H-Bond Acceptor:	28.0
H-Bond Donor:	14.0	Rings:	11.0
Heavy Atoms:	28.0

MedChem Properties

QED Drug-Likeness Score:	0.062	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.145	Fsp³:	0.29
MCE-18:	244.55 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.921	Fluc inhibitor:	0.232 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.718 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.665 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.079	Promiscuous compounds:	0.521

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.362	MDCK Permeability:	-5.366
Pgp-inhibitor:	0.0	Pgp-substrate:	0.02
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.006	30% Bioavailability (F30%):	0.857
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.007
Plasma Protein Binding (PPB):	85.449%	Volume Distribution (VD):	0.09
Fu:	9.202% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.874

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.838
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.996 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.337

Half-life (T1/2):

6.479

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.375
Human Hepatotoxicity (H-HT):	0.598	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.679	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.649	Skin Sensitization:	1.0
Carcinogencity:	0.036	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.969
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.153
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.133
A549 Cytotoxicity:	0.986	Hek293 Cytotoxicity:	0.996
BCF:	0.729 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.99 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.727 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.497 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	Flowers	Santana do Riacho, State Minas Gerais, Brazil	n.a.	PMID[22506638]
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Activity	1

Activity Type	# Activity
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.738	mM	PMID[22506638]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC470450 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	14574
0.1-0.2	31297
0.2-0.3	3045
0.3-0.4	572
0.4-0.5	259
0.5-0.6	78
0.6-0.7	21
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7766	Intermediate Similarity	NPC36138
0.7273	Intermediate Similarity	NPC470416
0.7128	Intermediate Similarity	NPC473571
0.7128	Intermediate Similarity	NPC110941
0.6939	Remote Similarity	NPC470447
0.6869	Remote Similarity	NPC470449
0.6733	Remote Similarity	NPC470455
0.6667	Remote Similarity	NPC488080
0.6667	Remote Similarity	NPC169977
0.6542	Remote Similarity	NPC488739
0.6531	Remote Similarity	NPC488074
0.6436	Remote Similarity	NPC85751
0.6436	Remote Similarity	NPC19240
0.6364	Remote Similarity	NPC488073
0.6364	Remote Similarity	NPC126784
0.6364	Remote Similarity	NPC241423
0.6214	Remote Similarity	NPC470445
0.6154	Remote Similarity	NPC470446
0.6126	Remote Similarity	NPC488740
0.61	Remote Similarity	NPC129264
0.6095	Remote Similarity	NPC214621
0.6095	Remote Similarity	NPC34267
0.604	Remote Similarity	NPC153755
0.6019	Remote Similarity	NPC217520
0.6	Remote Similarity	NPC223426
0.5981	Remote Similarity	NPC470451
0.5957	Remote Similarity	NPC305811
0.5926	Remote Similarity	NPC477895
0.5918	Remote Similarity	NPC116864
0.5918	Remote Similarity	NPC244776
0.5895	Remote Similarity	NPC42773
0.5895	Remote Similarity	NPC45522
0.5888	Remote Similarity	NPC121703
0.5882	Remote Similarity	NPC470125
0.58	Remote Similarity	NPC471079
0.5773	Remote Similarity	NPC101026
0.5773	Remote Similarity	NPC488077
0.5743	Remote Similarity	NPC173582
0.5743	Remote Similarity	NPC265885
0.5743	Remote Similarity	NPC181465
0.5743	Remote Similarity	NPC215710
0.5743	Remote Similarity	NPC473438
0.5743	Remote Similarity	NPC253788
0.5686	Remote Similarity	NPC65563
0.5686	Remote Similarity	NPC470949
0.5664	Remote Similarity	NPC488734
0.5664	Remote Similarity	NPC488735
0.5664	Remote Similarity	NPC488732
0.5664	Remote Similarity	NPC488738
0.5648	Remote Similarity	NPC81042
0.5644	Remote Similarity	NPC609888
0.5625	Remote Similarity	NPC139571
0.5619	Remote Similarity	NPC270448
0.5481	Remote Similarity	NPC186816
0.547	Remote Similarity	NPC488737
0.5464	Remote Similarity	NPC46420
0.5464	Remote Similarity	NPC24043
0.5446	Remote Similarity	NPC172807
0.537	Remote Similarity	NPC476472
0.537	Remote Similarity	NPC294815
0.537	Remote Similarity	NPC16194
0.5333	Remote Similarity	NPC470444
0.5327	Remote Similarity	NPC473327
0.5312	Remote Similarity	NPC111929
0.5312	Remote Similarity	NPC320283
0.5312	Remote Similarity	NPC41121
0.5299	Remote Similarity	NPC488736
0.5299	Remote Similarity	NPC488733
0.5288	Remote Similarity	NPC67326
0.5258	Remote Similarity	NPC77672
0.5258	Remote Similarity	NPC133671
0.5258	Remote Similarity	NPC135391
0.5258	Remote Similarity	NPC78263
0.5258	Remote Similarity	NPC250069
0.5254	Remote Similarity	NPC488079
0.5254	Remote Similarity	NPC488078
0.5238	Remote Similarity	NPC233994
0.5238	Remote Similarity	NPC203259
0.5238	Remote Similarity	NPC33054
0.5238	Remote Similarity	NPC176740
0.5238	Remote Similarity	NPC471725
0.5238	Remote Similarity	NPC134532
0.5238	Remote Similarity	NPC156869
0.5238	Remote Similarity	NPC602582
0.5229	Remote Similarity	NPC80068
0.52	Remote Similarity	NPC175107
0.5185	Remote Similarity	NPC37668
0.5176	Remote Similarity	NPC266960
0.514	Remote Similarity	NPC296018
0.5138	Remote Similarity	NPC270675
0.5138	Remote Similarity	NPC195685
0.5138	Remote Similarity	NPC486577
0.5133	Remote Similarity	NPC189564
0.513	Remote Similarity	NPC277532
0.5102	Remote Similarity	NPC249281
0.5093	Remote Similarity	NPC488364
0.5091	Remote Similarity	NPC471669
0.5089	Remote Similarity	NPC96605
0.5089	Remote Similarity	NPC280642
0.5088	Remote Similarity	NPC480796
0.5088	Remote Similarity	NPC472993
0.5051	Remote Similarity	NPC297987
0.5049	Remote Similarity	NPC276377

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC470450 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3612
0.1-0.2	5471
0.2-0.3	56
0.3-0.4	7
0.4-0.5	3
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5238	Remote Similarity	NPD6797	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data