NPASS Compound

Natural Product: NPC114484

Natural Product ID	NPC114484
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oleanolic Acid 3-O-Alpha-Rhamnopyranosyl-(1->3)-Beta-Glucuronopyranosyl28-O-Beta-Glucopyranoside
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2047216
PubChem CID	21635581
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 142149 0 0 0 0 0 0 0 0999 V2000 10.0426 1.1729 2.6312 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2615 2.2516 1.7562 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8272 1.6815 0.4866 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0346 0.7815 -0.1530 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9248 1.2380 -0.7965 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8056 0.9630 0.0421 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8582 0.0600 -0.3959 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0239 -0.4797 -1.5149 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6547 -0.3001 0.3973 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8820 0.9760 0.5729 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5054 0.7920 1.1132 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6767 -0.2145 0.3732 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4632 -1.1156 -0.5077 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8851 -1.7247 -1.5248 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4447 -1.5895 -1.8949 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7254 -0.6425 -0.9755 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6237 0.4658 -0.5267 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3990 1.1213 -1.6421 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9529 1.5442 0.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4969 1.8066 -0.1589 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2387 0.5370 -0.2811 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6463 -0.2465 -1.4243 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7124 0.4430 -2.7445 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5072 -1.4960 -1.5405 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2983 -1.7571 -0.2960 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3584 -0.6944 -0.0755 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7135 0.6473 -0.2471 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0439 1.4189 1.0465 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3241 1.4113 -1.3688 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3680 -0.8831 -0.9759 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5600 -1.3052 -0.3827 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7840 -2.5926 -0.8692 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0757 -3.0366 -0.7390 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8462 -3.0103 -1.9856 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0377 -3.3895 -1.9896 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2800 -2.5727 -3.1630 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8265 -2.3612 0.3735 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9200 -0.8971 0.0898 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7258 -0.3897 -0.6515 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4445 0.8881 -0.1663 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1311 -0.5531 -0.5100 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9264 0.2559 0.2654 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0894 -0.4596 0.5540 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9027 0.2402 1.4468 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1812 0.5734 2.7270 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4383 1.4598 0.7529 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.4091 2.2792 0.0485 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2463 1.5164 -0.4950 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1436 2.3726 -0.4886 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9918 3.3660 0.8437 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.4987 1.1106 -0.0809 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2191 -2.6488 1.5930 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9218 -1.3907 -0.2947 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0666 -2.7357 0.4174 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4919 -3.0111 0.7517 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1819 -1.8590 1.4592 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1699 -0.7435 1.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4805 -4.1633 1.7687 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3006 -3.5189 -0.4252 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0128 -1.1120 1.4052 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8973 2.6709 -1.1637 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2293 3.3233 -1.3183 C 0 0 2 0 0 0 0 0 0 0 0 0 11.3068 2.7303 -0.4791 C 0 0 2 0 0 0 0 0 0 0 0 0 12.2018 2.0758 -1.3577 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1083 4.6806 -0.9418 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2207 2.8180 -2.3977 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7243 0.4221 2.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3148 2.7748 1.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0344 2.8767 2.2206 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7570 1.1168 0.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8507 0.6345 -1.7510 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9701 1.5738 -0.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4493 1.5625 1.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6270 0.5003 2.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0318 1.7979 1.1574 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4640 -2.3907 -2.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0426 -2.6259 -1.8322 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4301 -1.3025 -2.9589 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5260 -1.2628 -0.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8333 1.2289 -2.5880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3750 0.6447 -1.8485 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6458 2.1528 -1.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0189 1.3987 1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4482 2.5394 0.0667 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5611 2.5098 -0.9880 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9324 2.3582 0.7278 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9596 -0.0694 0.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0515 -0.0332 -3.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7436 0.3234 -3.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5131 1.5113 -2.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9656 -2.3997 -1.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2724 -1.3640 -2.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8758 -2.7078 -0.4958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -1.9676 0.5961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7414 -0.8924 0.9594 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0112 2.5114 0.8778 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2995 1.0939 1.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0809 1.1699 1.3484 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6207 2.1196 -1.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8381 0.7546 -2.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1273 2.0626 -0.9669 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4568 -1.4019 0.7173 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0039 -4.1237 -0.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7817 -2.6636 -4.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8371 -2.8310 0.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9408 -0.3874 1.0967 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9117 -0.2536 -1.7383 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6449 1.0028 0.7835 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4524 0.5055 1.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7743 -0.4198 1.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3941 -0.1626 2.9740 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6939 1.5771 2.6728 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9124 0.5684 3.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8762 2.1147 1.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9268 2.7648 -0.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4770 1.1953 -1.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4414 3.3210 -0.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8220 3.8368 1.0961 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9805 0.3107 0.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8784 -2.8464 2.2872 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3442 -1.5745 -1.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4791 -2.7598 1.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6939 -3.5349 -0.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6085 -2.1411 2.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0389 -1.4558 0.8560 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7051 0.0788 2.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3776 -1.1995 2.3697 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6906 -4.0161 2.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4669 -4.1408 2.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4114 -5.1309 1.2337 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5822 -4.5879 -0.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2771 -2.9517 -0.4490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7551 -3.4096 -1.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0917 -0.6979 1.8213 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9503 -2.1680 1.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7311 -1.1585 2.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2709 3.2786 -0.4463 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5183 3.3684 -2.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9237 3.4693 0.0644 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6019 1.4991 -1.9249 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9810 4.9961 -0.5460 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2596 2.7275 -2.3062 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 9 7 1 6 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 26 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 51 1 0 37 52 1 0 13 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 55 58 1 0 55 59 1 0 12 60 1 1 5 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 61 66 1 0 63 3 1 0 57 9 1 0 53 9 1 0 17 12 1 0 27 21 1 0 39 31 1 0 48 42 1 0 22 16 1 0 1 67 1 0 2 68 1 0 2 69 1 0 3 70 1 1 5 71 1 6 10 72 1 0 10 73 1 0 11 74 1 0 11 75 1 0 14 76 1 0 15 77 1 0 15 78 1 0 16 79 1 1 18 80 1 0 18 81 1 0 18 82 1 0 19 83 1 0 19 84 1 0 20 85 1 0 20 86 1 0 21 87 1 1 23 88 1 0 23 89 1 0 23 90 1 0 24 91 1 0 24 92 1 0 25 93 1 0 25 94 1 0 26 95 1 1 28 96 1 0 28 97 1 0 28 98 1 0 29 99 1 0 29100 1 0 29101 1 0 31102 1 1 33103 1 1 36104 1 0 37105 1 1 38106 1 1 39107 1 6 40108 1 0 42109 1 1 44110 1 1 45111 1 0 45112 1 0 45113 1 0 46114 1 1 47115 1 6 48116 1 6 49117 1 0 50118 1 0 51119 1 0 52120 1 0 53121 1 6 54122 1 0 54123 1 0 56124 1 0 56125 1 0 57126 1 0 57127 1 0 58128 1 0 58129 1 0 58130 1 0 59131 1 0 59132 1 0 59133 1 0 60134 1 0 60135 1 0 60136 1 0 61137 1 1 62138 1 6 63139 1 1 64140 1 0 65141 1 0 66142 1 0 M END

Standard InCHIKey	LBHYRBPEXITYTN-WYPLEBMUSA-N
Standard InCHI	InChI=1S/C48H76O18/c1-21-28(50)30(52)32(54)39(61-21)64-36-34(56)37(38(58)59)65-41(35(36)57)63-27-12-13-45(6)25(44(27,4)5)11-14-47(8)26(45)10-9-22-23-19-43(2,3)15-17-48(23,18-16-46(22,47)7)42(60)66-40-33(55)31(53)29(51)24(20-49)62-40/h9,21,23-37,39-41,49-57H,10-20H2,1-8H3,(H,58,59)/t21-,23-,24+,25-,26+,27-,28-,29+,30+,31-,32+,33+,34-,35+,36-,37-,39-,40-,41+,45-,46+,47+,48-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@]23CC[C@@]4(C(=CC[C@H]5[C@@]4(C)CC[C@@H]4[C@]5(C)CC[C@@H](C4(C)C)O[C@@H]4O[C@H](C(=O)O)[C@H]([C@@H]([C@H]4O)O[C@@H]4O[C@@H](C)[C@@H]([C@H]([C@H]4O)O)O)O)[C@@H]3CC(CC2)(C)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	940.5	Volume:	920.627 ? Van der Waals volume.
Dense:	1.022	LogP:	1.785 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.378 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.29 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	46.0
TPSA:	291.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.093	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.29	Fsp³:	0.917
MCE-18:	176.696 ? 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:	0.91	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.2	Promiscuous compounds:	0.149

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.182	MDCK Permeability:	-5.108
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.581
20% Bioavailability (F20%):	0.353	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036	MRP1:	0.056
Plasma Protein Binding (PPB):	67.262%	Volume Distribution (VD):	-0.453
Fu:	24.392% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
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:	0.999	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.144 ? 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):

-0.072

Half-life (T1/2):

5.229

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.641	Drug-induced Liver Injury (DILI):	0.969
AMES Toxicity:	0.701	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.023	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.389	Drug-induced Nephrotoxicity:	0.981
Genotoxicity:	0.593	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.222	Hek293 Cytotoxicity:	0.18
BCF:	1.225 ? 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:	3.898 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.633 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.734 ? 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
NPO6683	Salacia petenensis	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[11270725]
NPO5192	Cistus albidus	Species	Cistaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19167901]
NPO32656	Stenocereus alamosensis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22704889]
NPO32619	isolatocereus dumortieri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22704889]
NPO5192	Cistus albidus	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38435667]
NPO5192	Cistus albidus	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32656	Stenocereus alamosensis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32619	isolatocereus dumortieri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5192	Cistus albidus	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6683	Salacia petenensis	Species	Celastraceae	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
IC50	1

Activity Type	# Activity
Cell line	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
NPT521	Cell line	RBL-2H3	Rattus norvegicus	IC50	>	200000.0	nM	PMID[22704889]

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 NPC114484 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	21242
0.1-0.2	24241
0.2-0.3	3077
0.3-0.4	714
0.4-0.5	339
0.5-0.6	122
0.6-0.7	53
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC159309
0.9565	High Similarity	NPC86222
0.8144	Intermediate Similarity	NPC157868
0.7745	Intermediate Similarity	NPC475591
0.7745	Intermediate Similarity	NPC236870
0.7692	Intermediate Similarity	NPC281148
0.7647	Intermediate Similarity	NPC40775
0.7647	Intermediate Similarity	NPC251768
0.7624	Intermediate Similarity	NPC192791
0.7576	Intermediate Similarity	NPC475516
0.7434	Intermediate Similarity	NPC21691
0.7426	Intermediate Similarity	NPC473884
0.7407	Intermediate Similarity	NPC11242
0.7315	Intermediate Similarity	NPC187290
0.7282	Intermediate Similarity	NPC223301
0.7282	Intermediate Similarity	NPC242840
0.7282	Intermediate Similarity	NPC171544
0.7172	Intermediate Similarity	NPC214484
0.713	Intermediate Similarity	NPC301449
0.713	Intermediate Similarity	NPC601290
0.7115	Intermediate Similarity	NPC112352
0.7059	Intermediate Similarity	NPC235405
0.703	Intermediate Similarity	NPC48499
0.7009	Intermediate Similarity	NPC258617
0.699	Remote Similarity	NPC249848
0.699	Remote Similarity	NPC107966
0.6981	Remote Similarity	NPC46665
0.6897	Remote Similarity	NPC4749
0.6887	Remote Similarity	NPC30735
0.6881	Remote Similarity	NPC104372
0.687	Remote Similarity	NPC475160
0.687	Remote Similarity	NPC473714
0.6827	Remote Similarity	NPC114441
0.6792	Remote Similarity	NPC75417
0.6762	Remote Similarity	NPC39211
0.6696	Remote Similarity	NPC481078
0.6695	Remote Similarity	NPC476068
0.6634	Remote Similarity	NPC209894
0.6609	Remote Similarity	NPC79643
0.6606	Remote Similarity	NPC235438
0.6581	Remote Similarity	NPC470218
0.6557	Remote Similarity	NPC302543
0.6518	Remote Similarity	NPC481079
0.6471	Remote Similarity	NPC481080
0.6393	Remote Similarity	NPC43550
0.6389	Remote Similarity	NPC469946
0.6387	Remote Similarity	NPC488560
0.6364	Remote Similarity	NPC10607
0.6364	Remote Similarity	NPC11551
0.6356	Remote Similarity	NPC123199
0.6346	Remote Similarity	NPC90856
0.6341	Remote Similarity	NPC305981
0.6339	Remote Similarity	NPC64715
0.6327	Remote Similarity	NPC167383
0.6316	Remote Similarity	NPC295823
0.6316	Remote Similarity	NPC174720
0.6316	Remote Similarity	NPC475467
0.6308	Remote Similarity	NPC475368
0.6306	Remote Similarity	NPC63159
0.629	Remote Similarity	NPC261506
0.629	Remote Similarity	NPC4328
0.625	Remote Similarity	NPC31193
0.625	Remote Similarity	NPC222580
0.6218	Remote Similarity	NPC135904
0.6207	Remote Similarity	NPC480936
0.6204	Remote Similarity	NPC58448
0.6204	Remote Similarity	NPC150400
0.62	Remote Similarity	NPC237503
0.6179	Remote Similarity	NPC41061
0.6179	Remote Similarity	NPC227551
0.6142	Remote Similarity	NPC250247
0.6106	Remote Similarity	NPC297263
0.6102	Remote Similarity	NPC475287
0.6091	Remote Similarity	NPC475171
0.608	Remote Similarity	NPC481081
0.6034	Remote Similarity	NPC80986
0.6	Remote Similarity	NPC295371
0.5966	Remote Similarity	NPC60557
0.5966	Remote Similarity	NPC67857
0.5965	Remote Similarity	NPC475504
0.5965	Remote Similarity	NPC609763
0.5963	Remote Similarity	NPC108748
0.5952	Remote Similarity	NPC236638
0.5952	Remote Similarity	NPC294453
0.5929	Remote Similarity	NPC44716
0.5902	Remote Similarity	NPC283417
0.5902	Remote Similarity	NPC200049
0.5897	Remote Similarity	NPC480473
0.5897	Remote Similarity	NPC480474
0.5877	Remote Similarity	NPC258885
0.5873	Remote Similarity	NPC293330
0.5873	Remote Similarity	NPC65105
0.5856	Remote Similarity	NPC6377
0.5856	Remote Similarity	NPC208381
0.5854	Remote Similarity	NPC47995
0.5847	Remote Similarity	NPC31838
0.5841	Remote Similarity	NPC160415
0.5833	Remote Similarity	NPC1046
0.5804	Remote Similarity	NPC161674
0.5789	Remote Similarity	NPC164389
0.5789	Remote Similarity	NPC473459
0.5789	Remote Similarity	NPC480475
0.5781	Remote Similarity	NPC298034
0.5781	Remote Similarity	NPC71065
0.5766	Remote Similarity	NPC173583
0.5763	Remote Similarity	NPC241909
0.576	Remote Similarity	NPC484061
0.576	Remote Similarity	NPC484062
0.576	Remote Similarity	NPC57484
0.5755	Remote Similarity	NPC128925
0.5741	Remote Similarity	NPC204458
0.5739	Remote Similarity	NPC148417
0.5739	Remote Similarity	NPC68175
0.5701	Remote Similarity	NPC480937
0.5688	Remote Similarity	NPC29069
0.5673	Remote Similarity	NPC606107
0.5669	Remote Similarity	NPC475514
0.5667	Remote Similarity	NPC75287
0.5656	Remote Similarity	NPC192600
0.5652	Remote Similarity	NPC180550
0.5652	Remote Similarity	NPC35405
0.5645	Remote Similarity	NPC100639
0.5645	Remote Similarity	NPC471550
0.5645	Remote Similarity	NPC191827
0.5641	Remote Similarity	NPC302887
0.563	Remote Similarity	NPC160452
0.5625	Remote Similarity	NPC473373
0.5596	Remote Similarity	NPC473481
0.5593	Remote Similarity	NPC114692
0.5586	Remote Similarity	NPC603870
0.5583	Remote Similarity	NPC477194
0.5565	Remote Similarity	NPC104071
0.5545	Remote Similarity	NPC78046
0.5526	Remote Similarity	NPC76497
0.5526	Remote Similarity	NPC22956
0.5522	Remote Similarity	NPC480422
0.5517	Remote Similarity	NPC102439
0.5508	Remote Similarity	NPC95437
0.5504	Remote Similarity	NPC484059
0.5504	Remote Similarity	NPC484060
0.55	Remote Similarity	NPC187618
0.55	Remote Similarity	NPC477193
0.5496	Remote Similarity	NPC70809
0.5495	Remote Similarity	NPC235841
0.5495	Remote Similarity	NPC297208
0.5462	Remote Similarity	NPC236657
0.5462	Remote Similarity	NPC202828
0.5462	Remote Similarity	NPC119592
0.5455	Remote Similarity	NPC224381
0.5447	Remote Similarity	NPC76972
0.5447	Remote Similarity	NPC469782
0.5447	Remote Similarity	NPC204414
0.5439	Remote Similarity	NPC472949
0.5433	Remote Similarity	NPC487505
0.5433	Remote Similarity	NPC478597
0.5431	Remote Similarity	NPC124296
0.5424	Remote Similarity	NPC470478
0.5424	Remote Similarity	NPC131469
0.5421	Remote Similarity	NPC31839
0.5417	Remote Similarity	NPC324875
0.5417	Remote Similarity	NPC292677
0.5403	Remote Similarity	NPC123522
0.5398	Remote Similarity	NPC25605
0.5378	Remote Similarity	NPC603832
0.5377	Remote Similarity	NPC306746
0.5377	Remote Similarity	NPC199457
0.5372	Remote Similarity	NPC96641
0.5372	Remote Similarity	NPC120116
0.5372	Remote Similarity	NPC163183
0.5357	Remote Similarity	NPC475208
0.5349	Remote Similarity	NPC478596
0.5338	Remote Similarity	NPC484063
0.5338	Remote Similarity	NPC220160
0.5338	Remote Similarity	NPC484064
0.5327	Remote Similarity	NPC68419
0.5317	Remote Similarity	NPC155410
0.5315	Remote Similarity	NPC30397
0.5299	Remote Similarity	NPC114304
0.5299	Remote Similarity	NPC309714
0.5299	Remote Similarity	NPC605226
0.5294	Remote Similarity	NPC257468
0.528	Remote Similarity	NPC478600
0.528	Remote Similarity	NPC478599
0.5268	Remote Similarity	NPC270667
0.5259	Remote Similarity	NPC263756
0.5259	Remote Similarity	NPC213674
0.5238	Remote Similarity	NPC475899
0.5234	Remote Similarity	NPC277212
0.5234	Remote Similarity	NPC30279
0.5234	Remote Similarity	NPC473918
0.5231	Remote Similarity	NPC286457
0.5227	Remote Similarity	NPC136768
0.5227	Remote Similarity	NPC135849
0.521	Remote Similarity	NPC118440
0.5203	Remote Similarity	NPC475486
0.5203	Remote Similarity	NPC36831
0.52	Remote Similarity	NPC313110
0.5185	Remote Similarity	NPC604133
0.5182	Remote Similarity	NPC256798

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC114484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6690
0.1-0.2	2387
0.2-0.3	66
0.3-0.4	6
0.4-0.5	1
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