NPASS Compound

Natural Product: NPC150400

Natural Product ID	NPC150400
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Galactopyranosyl-(1->3)-Beta-D-Glucopyranosylbayogenin28-O-Beta-D-Glucopyranosyl Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL488729
PubChem CID	44566262
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 146153 0 0 0 0 0 0 0 0999 V2000 -6.2192 2.1564 4.8611 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1289 1.8921 3.3682 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1477 3.1978 2.6509 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2628 0.9769 2.9726 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7472 -0.3901 2.6687 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7715 -0.4449 1.5036 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2533 -1.8405 1.4406 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0547 -2.0111 0.5643 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9194 -1.1672 1.0356 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2993 -1.8535 2.2305 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3489 0.1982 1.4855 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4045 1.1177 1.6692 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9596 0.8554 1.4533 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6876 -0.3678 0.6457 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5947 -0.2915 -0.1530 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6708 0.8245 -1.1123 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 -0.1048 0.8903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3938 -1.3855 1.2109 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1143 -1.8935 -0.0421 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1541 -1.9679 -1.2085 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6314 -1.2170 -2.4039 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1712 -3.4558 -1.6180 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4834 -3.8204 -1.9728 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7885 -1.6741 -0.7303 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3351 -1.9709 -1.6678 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5772 -2.1881 -0.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8821 -0.9053 -0.0681 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5446 0.0032 -1.0516 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1638 -0.9967 -0.2309 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3764 -1.6044 -0.0422 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3552 -1.4684 -1.1401 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7549 -1.4423 -0.5963 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9323 -2.4325 0.4962 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8582 -2.2165 1.5359 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4518 -1.9017 2.8748 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4678 -1.7416 3.8580 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0140 -1.1594 1.1591 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8084 -3.7496 0.0402 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2345 -0.1676 -0.3398 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2675 0.2257 -1.1585 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7093 1.3118 -2.0935 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3659 2.6519 -1.7442 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4041 2.7913 -0.2156 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2424 1.6663 0.3192 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7541 1.2033 1.6806 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7120 2.3766 2.4746 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4040 0.6733 -0.6003 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1060 2.5989 0.2754 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4875 3.6470 -2.1721 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9104 1.0466 -3.4179 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2752 -2.5152 -2.0756 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4408 -1.0366 2.1011 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7323 0.6005 1.7441 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8232 1.1603 3.1459 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5713 -0.1692 0.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7043 -1.0837 -0.5633 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1920 1.0313 0.0011 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9553 1.2661 -1.1624 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3531 1.6852 -0.8658 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1502 1.7086 -2.1436 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3906 2.1828 -3.3438 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9331 1.8734 -3.2949 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2059 2.4924 -4.4412 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8790 2.0924 -4.5190 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3736 2.1876 -2.0370 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9295 1.5063 -4.4641 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3156 2.4680 -2.0118 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9108 0.6766 -0.0441 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5970 1.4197 5.4228 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2873 2.1409 5.1835 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8295 3.1582 5.1266 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1580 3.5184 2.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7516 3.9870 3.3555 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5050 3.2569 1.7570 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9760 0.8607 3.8237 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8318 1.4642 2.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3466 -0.8373 3.5977 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6346 -0.9954 2.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1376 -2.2249 2.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0624 -2.4834 0.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7412 -3.0726 0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3737 -1.8429 -0.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8179 -1.1662 2.9460 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6526 -2.7130 1.9540 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1390 -2.3378 2.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6531 2.1260 1.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4240 1.7591 1.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5189 0.7895 2.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4369 -1.1734 1.4112 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6956 1.3037 -1.0703 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5513 0.5479 -2.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0163 1.6713 -0.9374 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3507 0.3599 1.8091 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4928 0.5870 0.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8185 -2.1444 1.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5383 -2.8795 0.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8225 -1.2284 -3.1637 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0912 -0.2488 -2.2214 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4539 -1.8403 -2.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5698 -3.6443 -2.5197 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8881 -4.0997 -0.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6029 -3.9361 -2.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6164 -2.3732 0.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1990 -2.8202 -2.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6162 -1.1086 -2.3075 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4035 -2.3988 -1.4873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3238 -3.0324 -0.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2205 -0.6587 -1.6758 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8927 0.4804 -1.7831 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2207 0.7598 -0.6174 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1852 -2.7013 0.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2378 -0.4893 -1.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4029 -1.8145 -1.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9041 -2.3835 1.0065 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1982 -3.1110 1.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0461 -2.7863 3.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1549 -1.0588 2.8853 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3477 -2.5465 4.4230 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5697 -3.9522 -0.5324 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4984 -0.6313 -1.8798 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6350 1.4570 -1.9308 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3481 2.6727 -2.2046 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7676 3.7903 0.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2508 2.1600 0.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4934 0.5361 2.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7214 0.8534 1.6506 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5667 2.5120 2.9480 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9675 3.0762 1.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9773 4.4937 -2.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8238 0.6900 -3.5557 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8489 -2.2556 -2.8443 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0794 -0.9135 3.0206 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9544 1.4434 1.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7025 0.3272 3.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0293 1.8712 3.3661 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9714 0.3084 -1.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4199 2.6425 -0.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5015 0.6520 -2.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5352 3.2578 -3.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8447 0.7491 -3.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7056 2.1754 -5.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2956 3.6077 -4.4420 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8170 1.2213 -4.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8325 0.5291 -4.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0428 1.9281 -1.6122 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3300 1.0478 0.7688 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 19 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 32 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 42 49 1 0 41 50 1 0 31 51 1 0 18 52 1 0 11 53 1 0 53 54 1 0 6 55 1 6 55 56 2 0 55 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 61 66 1 0 60 67 1 0 59 68 1 0 54 2 1 0 65 58 1 0 53 6 1 0 27 9 1 0 37 30 1 0 47 40 1 0 27 14 1 0 24 15 1 0 1 69 1 0 1 70 1 0 1 71 1 0 3 72 1 0 3 73 1 0 3 74 1 0 4 75 1 0 4 76 1 0 5 77 1 0 5 78 1 0 7 79 1 0 7 80 1 0 8 81 1 0 8 82 1 0 10 83 1 0 10 84 1 0 10 85 1 0 12 86 1 0 13 87 1 0 13 88 1 0 14 89 1 1 16 90 1 0 16 91 1 0 16 92 1 0 17 93 1 0 17 94 1 0 18 95 1 1 19 96 1 1 21 97 1 0 21 98 1 0 21 99 1 0 22100 1 0 22101 1 0 23102 1 0 24103 1 1 25104 1 0 25105 1 0 26106 1 0 26107 1 0 28108 1 0 28109 1 0 28110 1 0 30111 1 1 31112 1 6 32113 1 6 33114 1 1 34115 1 1 35116 1 0 35117 1 0 36118 1 0 38119 1 0 40120 1 6 41121 1 6 42122 1 6 43123 1 6 44124 1 1 45125 1 0 45126 1 0 46127 1 0 48128 1 0 49129 1 0 50130 1 0 51131 1 0 52132 1 0 53133 1 6 54134 1 0 54135 1 0 58136 1 6 59137 1 1 60138 1 6 61139 1 6 62140 1 6 63141 1 0 63142 1 0 64143 1 0 66144 1 0 67145 1 0 68146 1 0 M END

Standard InCHIKey	MWAZVBLWMOGSFL-RTZAAUDTSA-N
Standard InCHI	InChI=1S/C48H78O20/c1-43(2)11-13-48(42(62)68-40-35(60)33(58)30(55)25(18-50)64-40)14-12-46(5)21(22(48)15-43)7-8-28-44(3)16-23(53)38(45(4,20-52)27(44)9-10-47(28,46)6)67-41-36(61)37(31(56)26(19-51)65-41)66-39-34(59)32(57)29(54)24(17-49)63-39/h7,22-41,49-61H,8-20H2,1-6H3/t22-,23-,24+,25+,26+,27+,28+,29-,30+,31+,32-,33-,34+,35+,36+,37-,38-,39-,40-,41-,44-,45-,46+,47+,48-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O[C@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)O)O)O)O)[C@@H]2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	974.51	Volume:	940.844 ? Van der Waals volume.
Dense:	1.036	LogP:	0.456 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.691 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.526 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	45.0
TPSA:	335.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	13.0	Rings:	8.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.064	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.462	Fsp³:	0.938
MCE-18:	176.172 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.77	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.212	Promiscuous compounds:	0.074

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.913	MDCK Permeability:	-5.04
Pgp-inhibitor:	0.0	Pgp-substrate:	0.09
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):	0.858
20% Bioavailability (F20%):	0.601	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094	MRP1:	0.045
Plasma Protein Binding (PPB):	67.209%	Volume Distribution (VD):	-0.432
Fu:	22.785% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.434
HLM stability:	0.383 ? 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):

-0.157

Half-life (T1/2):

3.13

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.816	Drug-induced Liver Injury (DILI):	0.925
AMES Toxicity:	0.993	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.197	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.954	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.444	RPMI-8226 Immunitoxicity:	0.203
A549 Cytotoxicity:	0.986	Hek293 Cytotoxicity:	0.571
BCF:	1.049 ? 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:	3.387 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.721 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.841 ? 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
NPO28255	Caryocar glabrum	Species	Caryocaraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16499316]
NPO28255	Caryocar glabrum	Species	Caryocaraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28255	Caryocar glabrum	Species	Caryocaraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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
Others	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
NPT27	Others	Unspecified	n.a.	Activity	=	10.0	%	PMID[10869194]

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 NPC150400 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	22316
0.1-0.2	23113
0.2-0.3	3167
0.3-0.4	818
0.4-0.5	258
0.5-0.6	118
0.6-0.7	59
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
0.732	Intermediate Similarity	NPC473343
0.7188	Intermediate Similarity	NPC139894
0.7071	Intermediate Similarity	NPC223301
0.7071	Intermediate Similarity	NPC171544
0.6979	Remote Similarity	NPC475208
0.6837	Remote Similarity	NPC475516
0.6827	Remote Similarity	NPC104372
0.6813	Remote Similarity	NPC237503
0.6796	Remote Similarity	NPC475504
0.6778	Remote Similarity	NPC167383
0.6765	Remote Similarity	NPC473459
0.67	Remote Similarity	NPC295371
0.6635	Remote Similarity	NPC609763
0.6633	Remote Similarity	NPC48499
0.6545	Remote Similarity	NPC79643
0.6531	Remote Similarity	NPC29069
0.6486	Remote Similarity	NPC475899
0.6481	Remote Similarity	NPC481078
0.6466	Remote Similarity	NPC293330
0.6466	Remote Similarity	NPC65105
0.6465	Remote Similarity	NPC179434
0.6442	Remote Similarity	NPC159309
0.6442	Remote Similarity	NPC86222
0.6429	Remote Similarity	NPC214484
0.6422	Remote Similarity	NPC75287
0.6392	Remote Similarity	NPC209894
0.6389	Remote Similarity	NPC481030
0.6373	Remote Similarity	NPC473884
0.6356	Remote Similarity	NPC298034
0.6356	Remote Similarity	NPC71065
0.6348	Remote Similarity	NPC476068
0.6346	Remote Similarity	NPC309714
0.6316	Remote Similarity	NPC68419
0.6283	Remote Similarity	NPC123199
0.6275	Remote Similarity	NPC473373
0.625	Remote Similarity	NPC112352
0.6226	Remote Similarity	NPC63159
0.6214	Remote Similarity	NPC39211
0.6211	Remote Similarity	NPC306746
0.6211	Remote Similarity	NPC199457
0.6204	Remote Similarity	NPC114484
0.619	Remote Similarity	NPC30735
0.6176	Remote Similarity	NPC235405
0.6168	Remote Similarity	NPC222580
0.6154	Remote Similarity	NPC471547
0.6154	Remote Similarity	NPC469946
0.6146	Remote Similarity	NPC604133
0.6132	Remote Similarity	NPC251768
0.6121	Remote Similarity	NPC481080
0.6117	Remote Similarity	NPC249848
0.6117	Remote Similarity	NPC107966
0.6102	Remote Similarity	NPC41061
0.6102	Remote Similarity	NPC227551
0.6095	Remote Similarity	NPC192791
0.6087	Remote Similarity	NPC191827
0.6055	Remote Similarity	NPC281148
0.6053	Remote Similarity	NPC481031
0.605	Remote Similarity	NPC43550
0.6038	Remote Similarity	NPC471548
0.6016	Remote Similarity	NPC68767
0.6	Remote Similarity	NPC202828
0.6	Remote Similarity	NPC119592
0.6	Remote Similarity	NPC305981
0.5981	Remote Similarity	NPC40775
0.5981	Remote Similarity	NPC473401
0.5981	Remote Similarity	NPC10607
0.5968	Remote Similarity	NPC51099
0.595	Remote Similarity	NPC261506
0.595	Remote Similarity	NPC4328
0.5948	Remote Similarity	NPC475160
0.5948	Remote Similarity	NPC473714
0.5926	Remote Similarity	NPC235438
0.5905	Remote Similarity	NPC157868
0.5888	Remote Similarity	NPC109588
0.5877	Remote Similarity	NPC475287
0.5872	Remote Similarity	NPC297263
0.5868	Remote Similarity	NPC135849
0.5868	Remote Similarity	NPC481081
0.5833	Remote Similarity	NPC46665
0.5827	Remote Similarity	NPC275225
0.5826	Remote Similarity	NPC192600
0.5812	Remote Similarity	NPC100639
0.5806	Remote Similarity	NPC250247
0.5804	Remote Similarity	NPC241909
0.5804	Remote Similarity	NPC80986
0.5804	Remote Similarity	NPC69811
0.5794	Remote Similarity	NPC242840
0.5784	Remote Similarity	NPC90856
0.578	Remote Similarity	NPC475591
0.578	Remote Similarity	NPC236870
0.5752	Remote Similarity	NPC31838
0.5739	Remote Similarity	NPC76972
0.5739	Remote Similarity	NPC469782
0.5739	Remote Similarity	NPC204414
0.5728	Remote Similarity	NPC270667
0.5726	Remote Similarity	NPC142151
0.5714	Remote Similarity	NPC301449
0.5714	Remote Similarity	NPC481079
0.5714	Remote Similarity	NPC601290
0.5691	Remote Similarity	NPC144644
0.5691	Remote Similarity	NPC170407
0.5688	Remote Similarity	NPC102439
0.5678	Remote Similarity	NPC470218
0.5678	Remote Similarity	NPC471550
0.5664	Remote Similarity	NPC96641
0.5664	Remote Similarity	NPC163183
0.5635	Remote Similarity	NPC293031
0.5612	Remote Similarity	NPC116794
0.561	Remote Similarity	NPC236638
0.561	Remote Similarity	NPC294453
0.56	Remote Similarity	NPC271138
0.56	Remote Similarity	NPC110139
0.56	Remote Similarity	NPC108709
0.5596	Remote Similarity	NPC104071
0.5593	Remote Similarity	NPC155410
0.5593	Remote Similarity	NPC135904
0.5591	Remote Similarity	NPC153673
0.5545	Remote Similarity	NPC480475
0.5514	Remote Similarity	NPC58448
0.5514	Remote Similarity	NPC480420
0.551	Remote Similarity	NPC605954
0.55	Remote Similarity	NPC310014
0.55	Remote Similarity	NPC269315
0.55	Remote Similarity	NPC488560
0.5492	Remote Similarity	NPC480418
0.549	Remote Similarity	NPC256798
0.5481	Remote Similarity	NPC189884
0.5481	Remote Similarity	NPC238935
0.5481	Remote Similarity	NPC138334
0.5478	Remote Similarity	NPC187290
0.5462	Remote Similarity	NPC480419
0.5447	Remote Similarity	NPC475514
0.5446	Remote Similarity	NPC102914
0.5431	Remote Similarity	NPC815
0.5405	Remote Similarity	NPC11551
0.5405	Remote Similarity	NPC473383
0.54	Remote Similarity	NPC37739
0.5392	Remote Similarity	NPC220984
0.5391	Remote Similarity	NPC295823
0.5391	Remote Similarity	NPC174720
0.5391	Remote Similarity	NPC475467
0.537	Remote Similarity	NPC173583
0.5361	Remote Similarity	NPC191763
0.5354	Remote Similarity	NPC267694
0.5354	Remote Similarity	NPC46388
0.5347	Remote Similarity	NPC7870
0.5347	Remote Similarity	NPC75747
0.5339	Remote Similarity	NPC60557
0.5339	Remote Similarity	NPC67857
0.5323	Remote Similarity	NPC258617
0.5317	Remote Similarity	NPC37860
0.5283	Remote Similarity	NPC1046
0.5276	Remote Similarity	NPC70809
0.5268	Remote Similarity	NPC305267
0.5231	Remote Similarity	NPC110385
0.5197	Remote Similarity	NPC302543
0.5196	Remote Similarity	NPC137917
0.5189	Remote Similarity	NPC162354
0.5161	Remote Similarity	NPC57484
0.5154	Remote Similarity	NPC480417
0.5137	Remote Similarity	NPC469774
0.5135	Remote Similarity	NPC213674
0.5135	Remote Similarity	NPC475171
0.513	Remote Similarity	NPC64715
0.5128	Remote Similarity	NPC480474
0.5126	Remote Similarity	NPC476992
0.5116	Remote Similarity	NPC220160
0.5094	Remote Similarity	NPC47063
0.5093	Remote Similarity	NPC473127
0.5093	Remote Similarity	NPC110656
0.5086	Remote Similarity	NPC276093
0.5081	Remote Similarity	NPC487505
0.5078	Remote Similarity	NPC476991
0.5067	Remote Similarity	NPC469777
0.5048	Remote Similarity	NPC128925
0.5047	Remote Similarity	NPC204458
0.5044	Remote Similarity	NPC160415
0.5044	Remote Similarity	NPC114304
0.5042	Remote Similarity	NPC11242
0.504	Remote Similarity	NPC237191
0.5034	Remote Similarity	NPC469775

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC150400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7492
0.1-0.2	1595
0.2-0.3	59
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
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
		NPD

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