NPASS Compound

Natural Product: NPC192227

Natural Product ID	NPC192227
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KJWICSFRNHNDIM-DPCDSROHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325979
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 136143 0 0 0 0 0 0 0 0999 V2000 -6.8071 3.8440 0.7896 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6806 2.5983 1.6490 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7606 3.0215 3.1060 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7281 1.5649 1.3143 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1204 0.1826 1.3231 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1705 0.0110 0.1315 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5633 -1.3383 0.1174 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1894 -1.4276 -0.4966 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2240 -0.4751 0.1817 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1941 -0.8861 1.6143 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8232 0.8423 -0.0847 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0672 1.8014 -0.5672 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6235 1.7382 -0.8981 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0652 0.6255 -0.0225 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4039 0.6117 0.0596 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1095 0.8815 -1.2679 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7844 1.8352 0.9188 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2194 1.8829 1.2895 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9226 0.5830 1.4592 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9274 -0.4677 1.7867 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6862 -1.8051 1.8588 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3898 -0.2235 3.1539 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9357 -0.6077 0.7000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1367 -1.6026 1.1668 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0726 -1.7972 0.0293 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8264 -0.5832 -0.4032 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0590 -0.7236 -1.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7820 0.2765 0.4157 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1043 0.1594 0.7658 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6584 -1.1761 0.3460 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8080 -0.9419 -0.6271 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8385 -0.1227 0.1026 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1560 1.1305 0.6198 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8448 1.2001 0.1479 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9023 0.2740 -0.6796 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1232 -0.1260 -0.1988 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8100 -1.0290 -1.1813 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8597 -0.2635 -1.9699 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8910 0.3016 -1.0486 C 0 0 1 0 0 0 0 0 0 0 0 0 12.2678 0.5575 0.2967 C 0 0 1 0 0 0 0 0 0 0 0 0 12.9919 1.6379 1.0684 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3750 1.7307 2.3203 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9301 0.9474 0.1826 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9072 -0.6460 -0.8530 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2395 0.8035 -2.6234 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3425 -2.1460 -0.5669 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3182 -0.2124 -1.6936 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1998 -1.8826 1.4118 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2484 1.1688 0.1598 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3225 1.9985 1.4313 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1129 0.0873 -1.0551 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9638 0.9615 -1.9473 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1571 -0.7949 -1.1928 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0863 -0.8116 -2.2596 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1698 -2.1483 -2.9294 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2709 -2.9934 -2.3054 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.6116 -2.2928 -2.3436 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.3895 -0.8022 -2.5443 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3338 -0.4618 -1.6957 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2200 -2.4341 -1.0965 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8837 -3.1958 -0.9683 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4703 -2.0201 -4.2819 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5275 3.6585 -0.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0199 4.7521 1.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8306 4.0625 0.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8017 3.1729 3.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2147 3.9890 3.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1971 2.3031 3.7363 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5046 1.5981 2.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1514 1.8171 0.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5141 0.0579 2.2204 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9741 -0.5438 1.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1781 -2.0351 -0.5452 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6469 -1.9028 1.0941 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8754 -2.4828 -0.4030 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3430 -1.1442 -1.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7465 -1.8963 1.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1814 -0.9886 2.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6381 -0.2313 2.2820 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5054 2.8136 -0.7775 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1140 2.6944 -0.7775 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5006 1.4801 -1.9965 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4233 0.8992 1.0216 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6182 -0.0592 -1.6294 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9499 1.5901 -1.1135 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4821 1.3396 -2.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6413 2.7256 0.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0659 2.0125 1.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8516 2.4990 0.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 2.4663 2.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6000 0.6569 2.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7556 -2.2538 0.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1122 -2.4579 2.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6443 -1.6052 2.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0861 0.4453 3.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3710 -1.1721 3.7681 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3995 0.2036 3.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4626 -1.1945 -0.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4107 -2.5628 1.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5107 -1.2046 2.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7033 -2.7074 0.1160 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3862 -2.0663 -0.8383 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8020 -0.0465 -2.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1367 -0.6168 -2.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3503 -1.8040 -2.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3099 0.2959 1.8458 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8731 -1.7982 -0.1324 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1854 -1.9070 -0.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2372 -0.6887 0.9754 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1769 1.1552 1.7287 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6708 2.0545 0.2844 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9530 -0.7105 0.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0526 -1.3688 -1.9235 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3044 -0.9750 -2.7017 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3424 1.2416 -1.4267 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2931 -0.3643 0.9303 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7541 2.6123 0.5533 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0708 1.5008 1.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4064 1.8875 2.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5859 -0.6231 -1.5514 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5894 1.6866 -2.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2500 -2.2944 -0.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8318 -0.3610 -2.5381 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7651 -2.7683 1.4812 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6366 1.9104 -0.5903 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9962 1.4927 2.3221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6200 2.8594 1.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8978 -0.0328 -3.0199 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2332 -2.7347 -2.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3512 -3.9689 -2.7817 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2782 -2.6993 -3.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1560 -0.5656 -3.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2719 -0.2322 -2.1954 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5273 -2.2426 -0.4046 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2675 -3.9428 -0.8558 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7534 -1.5001 -4.7538 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 0 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 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 19 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 31 47 1 0 30 48 1 0 11 49 1 0 49 50 1 0 6 51 1 6 51 52 2 0 51 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 57 60 1 0 56 61 1 0 55 62 1 0 50 2 1 0 59 54 1 0 49 6 1 0 26 9 1 0 34 29 1 0 43 36 1 0 26 14 1 0 23 15 1 0 1 63 1 0 1 64 1 0 1 65 1 0 3 66 1 0 3 67 1 0 3 68 1 0 4 69 1 0 4 70 1 0 5 71 1 0 5 72 1 0 7 73 1 0 7 74 1 0 8 75 1 0 8 76 1 0 10 77 1 0 10 78 1 0 10 79 1 0 12 80 1 0 13 81 1 0 13 82 1 0 14 83 1 0 16 84 1 0 16 85 1 0 16 86 1 0 17 87 1 0 17 88 1 0 18 89 1 0 18 90 1 0 19 91 1 1 21 92 1 0 21 93 1 0 21 94 1 0 22 95 1 0 22 96 1 0 22 97 1 0 23 98 1 0 24 99 1 0 24100 1 0 25101 1 0 25102 1 0 27103 1 0 27104 1 0 27105 1 0 29106 1 1 30107 1 6 31108 1 6 32109 1 1 33110 1 0 33111 1 0 36112 1 1 37113 1 6 38114 1 6 39115 1 6 40116 1 1 41117 1 0 41118 1 0 42119 1 0 44120 1 0 45121 1 0 46122 1 0 47123 1 0 48124 1 0 49125 1 0 50126 1 0 50127 1 0 54128 1 6 55129 1 6 56130 1 6 57131 1 6 58132 1 0 58133 1 0 60134 1 0 61135 1 0 62136 1 0 M END

Standard InCHIKey	KJWICSFRNHNDIM-DPCDSROHSA-N
Standard InCHI	InChI=1S/C46H74O16/c1-41(2)14-16-46(40(56)62-38-34(53)30(49)24(48)20-57-38)17-15-44(6)22(23(46)18-41)8-9-28-43(5)12-11-29(42(3,4)27(43)10-13-45(28,44)7)61-37-35(54)32(51)26(21-58-37)60-39-36(55)33(52)31(50)25(19-47)59-39/h8,23-39,47-55H,9-21H2,1-7H3/t23?,24-,25+,26-,27?,28?,29-,30-,31+,32-,33-,34+,35+,36+,37-,38-,39-,43-,44?,45+,46-/m0/s1
SMILES	CC1(C)CC[C@@]2(CCC3(C)C(=CCC4[C@@]5(C)CC[C@@H](C(C)(C)C5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O)C2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	882.5	Volume:	871.091 ? Van der Waals volume.
Dense:	1.013	LogP:	3.146 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.551 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.338 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	45.0
TPSA:	254.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	8.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.1	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.166	Fsp³:	0.935
MCE-18:	169.978 ? 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:	0.905	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.034 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.148	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.096	MDCK Permeability:	-5.148
Pgp-inhibitor:	0.0	Pgp-substrate:	0.152
PAMPA:	0.999 ? 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):	0.004
20% Bioavailability (F20%):	0.112	30% Bioavailability (F30%):	0.959
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.25
Plasma Protein Binding (PPB):	72.556%	Volume Distribution (VD):	-0.34
Fu:	16.754% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.031
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.073
HLM stability:	0.926 ? 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):

0.088

Half-life (T1/2):

2.513

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.011
Human Hepatotoxicity (H-HT):	0.917	Drug-induced Liver Injury (DILI):	0.699
AMES Toxicity:	0.941	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.025	Skin Sensitization:	1.0
Carcinogencity:	0.138	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.265	Drug-induced Nephrotoxicity:	0.902
Genotoxicity:	0.246	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	0.969	Hek293 Cytotoxicity:	0.753
BCF:	2.346 ? 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:	4.719 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.901 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.383 ? 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
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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

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

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 NPC192227 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	20930
0.1-0.2	23945
0.2-0.3	3399
0.3-0.4	917
0.4-0.5	373
0.5-0.6	71
0.6-0.7	79
0.7-0.8	0
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8864	High Similarity	NPC48499
0.8478	Intermediate Similarity	NPC295371
0.8265	Intermediate Similarity	NPC481079
0.8229	Intermediate Similarity	NPC63159
0.8182	Intermediate Similarity	NPC295823
0.8182	Intermediate Similarity	NPC174720
0.8182	Intermediate Similarity	NPC475467
0.8095	Intermediate Similarity	NPC481080
0.8	Intermediate Similarity	NPC469946
0.7826	Intermediate Similarity	NPC90856
0.7642	Intermediate Similarity	NPC123199
0.76	Intermediate Similarity	NPC297263
0.7568	Intermediate Similarity	NPC481081
0.75	Intermediate Similarity	NPC488560
0.75	Intermediate Similarity	NPC475516
0.7477	Intermediate Similarity	NPC135904
0.7476	Intermediate Similarity	NPC241909
0.7453	Intermediate Similarity	NPC79643
0.7447	Intermediate Similarity	NPC214484
0.7423	Intermediate Similarity	NPC473373
0.7407	Intermediate Similarity	NPC475160
0.7407	Intermediate Similarity	NPC473714
0.7404	Intermediate Similarity	NPC31838
0.7379	Intermediate Similarity	NPC301449
0.7379	Intermediate Similarity	NPC601290
0.7374	Intermediate Similarity	NPC112352
0.7368	Intermediate Similarity	NPC1046
0.7368	Intermediate Similarity	NPC29069
0.7347	Intermediate Similarity	NPC39211
0.732	Intermediate Similarity	NPC235405
0.7312	Intermediate Similarity	NPC128925
0.7245	Intermediate Similarity	NPC249848
0.7245	Intermediate Similarity	NPC107966
0.7238	Intermediate Similarity	NPC481078
0.7238	Intermediate Similarity	NPC187290
0.7196	Intermediate Similarity	NPC60557
0.7196	Intermediate Similarity	NPC67857
0.7157	Intermediate Similarity	NPC235438
0.7155	Intermediate Similarity	NPC250247
0.7129	Intermediate Similarity	NPC30735
0.7091	Intermediate Similarity	NPC470218
0.7083	Intermediate Similarity	NPC204458
0.708	Intermediate Similarity	NPC41061
0.708	Intermediate Similarity	NPC227551
0.7054	Intermediate Similarity	NPC476068
0.7043	Intermediate Similarity	NPC261506
0.7043	Intermediate Similarity	NPC4328
0.703	Intermediate Similarity	NPC223301
0.703	Intermediate Similarity	NPC171544
0.701	Intermediate Similarity	NPC78046
0.6983	Remote Similarity	NPC70809
0.6957	Remote Similarity	NPC236638
0.6957	Remote Similarity	NPC294453
0.6957	Remote Similarity	NPC305981
0.6952	Remote Similarity	NPC104372
0.6923	Remote Similarity	NPC222580
0.6893	Remote Similarity	NPC40775
0.6893	Remote Similarity	NPC251768
0.6832	Remote Similarity	NPC157868
0.6827	Remote Similarity	NPC148417
0.6783	Remote Similarity	NPC258617
0.6754	Remote Similarity	NPC57484
0.6731	Remote Similarity	NPC159309
0.6731	Remote Similarity	NPC473459
0.6731	Remote Similarity	NPC46665
0.6731	Remote Similarity	NPC86222
0.6724	Remote Similarity	NPC43550
0.6699	Remote Similarity	NPC192791
0.6667	Remote Similarity	NPC475591
0.6667	Remote Similarity	NPC236870
0.6636	Remote Similarity	NPC281148
0.6602	Remote Similarity	NPC263756
0.6602	Remote Similarity	NPC473343
0.6602	Remote Similarity	NPC213674
0.6598	Remote Similarity	NPC256798
0.6596	Remote Similarity	NPC237503
0.6577	Remote Similarity	NPC76972
0.6577	Remote Similarity	NPC469782
0.6577	Remote Similarity	NPC204414
0.6571	Remote Similarity	NPC10607
0.6571	Remote Similarity	NPC480475
0.6559	Remote Similarity	NPC167383
0.6514	Remote Similarity	NPC80986
0.65	Remote Similarity	NPC224381
0.6491	Remote Similarity	NPC100639
0.6481	Remote Similarity	NPC114484
0.6476	Remote Similarity	NPC104071
0.6471	Remote Similarity	NPC298034
0.6471	Remote Similarity	NPC71065
0.6455	Remote Similarity	NPC104137
0.6455	Remote Similarity	NPC26626
0.6415	Remote Similarity	NPC488526
0.6415	Remote Similarity	NPC102439
0.64	Remote Similarity	NPC189884
0.64	Remote Similarity	NPC138334
0.6387	Remote Similarity	NPC202828
0.6387	Remote Similarity	NPC119592
0.6372	Remote Similarity	NPC192600
0.6348	Remote Similarity	NPC191827
0.6321	Remote Similarity	NPC109588
0.6311	Remote Similarity	NPC139894
0.6283	Remote Similarity	NPC475287
0.6262	Remote Similarity	NPC164389
0.625	Remote Similarity	NPC173583
0.625	Remote Similarity	NPC480420
0.62	Remote Similarity	NPC209894
0.619	Remote Similarity	NPC473884
0.619	Remote Similarity	NPC470512
0.6174	Remote Similarity	NPC165204
0.6168	Remote Similarity	NPC309714
0.6167	Remote Similarity	NPC65105
0.616	Remote Similarity	NPC480422
0.6147	Remote Similarity	NPC609763
0.6121	Remote Similarity	NPC155410
0.6121	Remote Similarity	NPC480419
0.6116	Remote Similarity	NPC136768
0.6106	Remote Similarity	NPC11242
0.6095	Remote Similarity	NPC58448
0.6095	Remote Similarity	NPC150400
0.6075	Remote Similarity	NPC242840
0.6071	Remote Similarity	NPC480473
0.6071	Remote Similarity	NPC480474
0.6033	Remote Similarity	NPC293330
0.6019	Remote Similarity	NPC160415
0.6019	Remote Similarity	NPC117714
0.6019	Remote Similarity	NPC30289
0.6	Remote Similarity	NPC110633
0.6	Remote Similarity	NPC480418
0.6	Remote Similarity	NPC475504
0.5981	Remote Similarity	NPC76497
0.598	Remote Similarity	NPC161434
0.5968	Remote Similarity	NPC220160
0.5966	Remote Similarity	NPC85154
0.5963	Remote Similarity	NPC173859
0.5963	Remote Similarity	NPC148603
0.595	Remote Similarity	NPC475514
0.5948	Remote Similarity	NPC123522
0.5932	Remote Similarity	NPC283417
0.5932	Remote Similarity	NPC200049
0.5913	Remote Similarity	NPC185466
0.5909	Remote Similarity	NPC470515
0.5905	Remote Similarity	NPC136877
0.5897	Remote Similarity	NPC475899
0.5888	Remote Similarity	NPC488516
0.5877	Remote Similarity	NPC207738
0.5868	Remote Similarity	NPC13998
0.5868	Remote Similarity	NPC286457
0.5865	Remote Similarity	NPC472268
0.5862	Remote Similarity	NPC610204
0.5833	Remote Similarity	NPC4749
0.5818	Remote Similarity	NPC232237
0.5804	Remote Similarity	NPC64715
0.5789	Remote Similarity	NPC297950
0.5766	Remote Similarity	NPC105800
0.5736	Remote Similarity	NPC33012
0.5714	Remote Similarity	NPC470513
0.57	Remote Similarity	NPC306746
0.57	Remote Similarity	NPC199457
0.5691	Remote Similarity	NPC470876
0.5688	Remote Similarity	NPC471547
0.5688	Remote Similarity	NPC161674
0.5682	Remote Similarity	NPC489208
0.568	Remote Similarity	NPC309223
0.5676	Remote Similarity	NPC473401
0.5676	Remote Similarity	NPC104400
0.5676	Remote Similarity	NPC10320
0.5662	Remote Similarity	NPC45606
0.566	Remote Similarity	NPC179434
0.5659	Remote Similarity	NPC8524
0.5644	Remote Similarity	NPC68419
0.5636	Remote Similarity	NPC75417
0.5625	Remote Similarity	NPC480417
0.5593	Remote Similarity	NPC300419
0.5593	Remote Similarity	NPC607904
0.5586	Remote Similarity	NPC471548
0.5583	Remote Similarity	NPC219180
0.5575	Remote Similarity	NPC470514
0.5565	Remote Similarity	NPC606145
0.5556	Remote Similarity	NPC302543
0.5556	Remote Similarity	NPC75287
0.5537	Remote Similarity	NPC471550
0.5536	Remote Similarity	NPC305267
0.5528	Remote Similarity	NPC21691
0.5526	Remote Similarity	NPC488515
0.5517	Remote Similarity	NPC469778
0.5508	Remote Similarity	NPC288205
0.5508	Remote Similarity	NPC51465
0.5504	Remote Similarity	NPC102505
0.5504	Remote Similarity	NPC488514
0.55	Remote Similarity	NPC470911
0.5489	Remote Similarity	NPC475368
0.5487	Remote Similarity	NPC68175
0.547	Remote Similarity	NPC473826
0.547	Remote Similarity	NPC609281
0.5462	Remote Similarity	NPC610461
0.5455	Remote Similarity	NPC166422
0.5455	Remote Similarity	NPC469776
0.5455	Remote Similarity	NPC472269
0.5455	Remote Similarity	NPC488561
0.5448	Remote Similarity	NPC32723

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC192227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7214
0.1-0.2	1874
0.2-0.3	53
0.3-0.4	8
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