NPASS Compound

Natural Product: NPC473481

Natural Product ID	NPC473481
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1S,2R,4As,6Ar,6Ar,6Br,8Ar,10S,12Ar,14Bs)-1,2,6B,9,9,12A-Hexamethyl-10-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-6A-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxycarbonyl-2,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydro-1H-Picene-4A-Carboxylic Acid
IUPAC Name	(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL443103
PubChem CID	44567120
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 123129 0 0 0 0 0 0 0 0999 V2000 -6.8592 -2.5226 -0.9309 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6883 -3.1683 -0.2413 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0505 -3.4413 1.1770 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0260 -2.8172 2.1131 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6796 -3.3412 1.6787 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6005 -3.0039 2.6138 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9375 -1.6703 2.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7651 -1.1083 1.1334 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0262 -2.2444 0.2641 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0648 -2.7897 -0.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3486 -2.3532 -0.4554 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6676 -1.1750 0.3724 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4283 -0.4459 1.0489 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5574 0.9721 0.4231 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7476 1.7274 0.4587 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9504 0.8948 0.2673 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5618 -0.2981 -0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8591 -1.0977 -0.7483 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9524 -0.6847 0.1831 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3715 0.7795 -0.0493 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1619 1.6341 -0.2303 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3308 2.8485 0.6957 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0747 2.1483 -1.6147 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2706 0.8606 -1.0806 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5347 1.1339 -0.6186 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1988 2.3426 -1.2168 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5176 2.5409 -0.4552 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3288 1.2841 -0.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4978 0.0491 -0.2685 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3328 0.0270 -0.9968 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3199 -1.1636 -0.5983 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5237 -1.1880 0.1209 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3313 1.3385 0.4327 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2021 2.7992 0.8737 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4593 3.4987 -0.9683 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9936 -0.0567 -1.8761 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0190 -0.1069 2.4841 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3565 -2.8932 0.2532 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5024 -2.1747 -0.3340 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2753 -2.0030 -1.8136 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7727 -0.0289 0.9355 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4602 0.3906 1.9446 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0669 0.5952 -0.2318 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0026 1.6203 -0.4195 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2558 2.8233 -0.9313 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2215 3.9418 -1.1189 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6334 3.6592 -0.7451 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0808 2.2571 -1.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0618 1.3623 -1.2250 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9263 1.8136 0.1262 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4767 0.5645 -0.0610 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8923 4.0186 0.5985 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7911 5.0102 -0.2945 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5929 2.5220 -2.1201 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8235 -4.8459 1.7250 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6374 -5.4808 0.6682 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1470 -5.5391 2.8685 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6353 -2.2115 -0.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5217 -1.5987 -1.4266 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3178 -3.1863 -1.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4450 -4.0816 -0.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9627 -4.5522 1.3518 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0820 -3.1845 1.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1074 -1.7380 2.1673 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2215 -3.3138 3.1109 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0392 -3.0795 3.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8473 -3.8492 2.6254 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9724 -1.8360 3.0623 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 -0.9627 3.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3468 -3.6472 -1.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6739 -2.3132 -1.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9320 -3.2647 -0.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4151 -1.5022 1.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2114 1.5046 1.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9435 0.9391 -0.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6609 2.4684 -0.4049 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8828 2.3893 1.3329 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3184 0.4685 1.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2388 -0.9298 -1.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6792 -2.1709 -0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8478 -1.3041 -0.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8025 -0.9095 1.2366 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9375 1.0161 0.9061 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9920 2.5130 1.6981 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4133 3.0681 0.7994 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7433 3.7007 0.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2389 2.8689 -1.7787 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1695 1.3857 -2.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9878 2.7970 -1.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5841 1.2548 0.5009 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4155 2.2213 -2.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0890 3.3698 -0.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7990 1.1615 -1.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2858 0.0219 0.8173 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7735 -2.0886 -0.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5801 -1.2129 -1.6852 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1849 -1.7758 -0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1002 0.8218 1.2338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5169 2.0927 1.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7345 3.9372 -0.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8303 1.0064 -2.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6581 -0.4391 -2.7155 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0246 -0.5503 -2.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9156 0.1101 3.1384 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4953 0.9038 2.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7032 -0.7979 2.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3212 -3.8647 -0.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8831 -1.2955 0.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1627 -1.8585 -1.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4894 -2.9613 -2.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7419 -1.1371 -2.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4120 1.8315 0.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4811 3.0559 -0.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1071 4.3332 -2.1549 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2815 4.3453 -1.3439 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7361 2.2329 -1.9440 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3764 1.8942 1.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7633 2.5676 0.2509 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0164 -0.0381 0.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2079 4.6145 0.9437 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2459 5.6637 -0.7870 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0522 1.8476 -2.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1823 -6.5666 2.8792 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 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 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 1 0 29 31 1 0 31 32 1 0 28 33 1 0 27 34 1 0 26 35 1 0 17 36 1 0 13 37 1 0 9 38 1 0 38 39 1 0 39 40 1 0 8 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 47 52 1 0 46 53 1 0 45 54 1 0 5 55 1 0 55 56 2 0 55 57 1 0 39 2 1 0 38 5 1 0 13 8 1 0 17 12 1 0 21 16 1 0 30 25 1 0 49 44 1 0 1 58 1 0 1 59 1 0 1 60 1 0 2 61 1 0 3 62 1 0 3 63 1 0 4 64 1 0 4 65 1 0 6 66 1 0 6 67 1 0 7 68 1 0 7 69 1 0 10 70 1 0 11 71 1 0 11 72 1 0 12 73 1 0 14 74 1 0 14 75 1 0 15 76 1 0 15 77 1 0 16 78 1 0 18 79 1 0 18 80 1 0 19 81 1 0 19 82 1 0 20 83 1 0 22 84 1 0 22 85 1 0 22 86 1 0 23 87 1 0 23 88 1 0 23 89 1 0 25 90 1 0 26 91 1 0 27 92 1 0 28 93 1 0 29 94 1 0 31 95 1 0 31 96 1 0 32 97 1 0 33 98 1 0 34 99 1 0 35100 1 0 36101 1 0 36102 1 0 36103 1 0 37104 1 0 37105 1 0 37106 1 0 38107 1 0 39108 1 0 40109 1 0 40110 1 0 40111 1 0 44112 1 0 45113 1 0 46114 1 0 47115 1 0 48116 1 0 50117 1 0 50118 1 0 51119 1 0 52120 1 0 53121 1 0 54122 1 0 57123 1 0 M END

Standard InCHIKey	PBSNQNFMNFWRCH-DTJUAWDLSA-N
Standard InCHI	InChI=1S/C42H66O15/c1-19-9-14-41(36(51)52)15-16-42(37(53)57-35-33(50)31(48)29(46)23(18-44)55-35)21(27(41)20(19)2)7-8-25-39(5)12-11-26(38(3,4)24(39)10-13-40(25,42)6)56-34-32(49)30(47)28(45)22(17-43)54-34/h7,19-20,22-35,43-50H,8-18H2,1-6H3,(H,51,52)/t19-,20+,22-,23-,24+,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,39+,40-,41+,42-/m1/s1
SMILES	CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)C)C2C1C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	810.44	Volume:	799.037 ? Van der Waals volume.
Dense:	1.014	LogP:	1.932 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.828 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.97 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	40.0
TPSA:	253.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	15.0

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:	5.92	Fsp³:	0.905
MCE-18:	151.25 ? 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:	0.153	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.332 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.43	MDCK Permeability:	-5.014
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
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):	0.986
20% Bioavailability (F20%):	0.041	30% Bioavailability (F30%):	0.972
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	1.0
Plasma Protein Binding (PPB):	56.347%	Volume Distribution (VD):	-0.419
Fu:	29.452% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.216	BCRP inhibitor:	0.0
BSEP inhibitor:	0.025

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.966	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	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:	0.0
HLM stability:	0.0 ? 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):

0.405

Half-life (T1/2):

2.652

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.139
Human Hepatotoxicity (H-HT):	0.466	Drug-induced Liver Injury (DILI):	0.239
AMES Toxicity:	0.079	Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.42	Skin Sensitization:	0.012
Carcinogencity:	0.043	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.109	Ototoxicity:	1.0
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	0.05
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.028	Hek293 Cytotoxicity:	0.322
BCF:	0.509 ? 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:	4.177 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.182 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.292 ? 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
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919590]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25311	Guettarda platypoda	Species	Rubiaceae	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
MIC50	1

Activity Type	# Activity
Organism	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
NPT2516	Organism	Vesicular stomatitis Indiana virus	Vesicular stomatitis Indiana virus	MIC50	=	87000.0	nM	PMID[16441083]

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 NPC473481 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	17920
0.1-0.2	25787
0.2-0.3	4491
0.3-0.4	1124
0.4-0.5	412
0.5-0.6	99
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC108748
0.8764	High Similarity	NPC258885
0.7326	Intermediate Similarity	NPC57362
0.6818	Remote Similarity	NPC274507
0.6556	Remote Similarity	NPC606107
0.6421	Remote Similarity	NPC30397
0.6289	Remote Similarity	NPC235841
0.6289	Remote Similarity	NPC297208
0.6186	Remote Similarity	NPC211798
0.6129	Remote Similarity	NPC177246
0.6064	Remote Similarity	NPC31839
0.6044	Remote Similarity	NPC484195
0.5914	Remote Similarity	NPC204407
0.5882	Remote Similarity	NPC157868
0.5865	Remote Similarity	NPC124296
0.5859	Remote Similarity	NPC164194
0.5825	Remote Similarity	NPC475171
0.581	Remote Similarity	NPC40775
0.581	Remote Similarity	NPC159309
0.581	Remote Similarity	NPC180550
0.581	Remote Similarity	NPC35405
0.581	Remote Similarity	NPC86222
0.5784	Remote Similarity	NPC127056
0.5773	Remote Similarity	NPC128925
0.5769	Remote Similarity	NPC192791
0.5769	Remote Similarity	NPC75417
0.5758	Remote Similarity	NPC90856
0.5758	Remote Similarity	NPC214484
0.5747	Remote Similarity	NPC485589
0.566	Remote Similarity	NPC251768
0.5644	Remote Similarity	NPC48499
0.5631	Remote Similarity	NPC109079
0.5607	Remote Similarity	NPC475591
0.5607	Remote Similarity	NPC236870
0.5596	Remote Similarity	NPC281148
0.5596	Remote Similarity	NPC114484
0.5577	Remote Similarity	NPC472949
0.5556	Remote Similarity	NPC209894
0.5534	Remote Similarity	NPC235405
0.5534	Remote Similarity	NPC25605
0.5534	Remote Similarity	NPC475516
0.5524	Remote Similarity	NPC22956
0.5495	Remote Similarity	NPC485586
0.5495	Remote Similarity	NPC485588
0.5481	Remote Similarity	NPC249848
0.5481	Remote Similarity	NPC107966
0.5446	Remote Similarity	NPC204458
0.5437	Remote Similarity	NPC136877
0.5429	Remote Similarity	NPC473884
0.5429	Remote Similarity	NPC39211
0.5421	Remote Similarity	NPC114304
0.5413	Remote Similarity	NPC257468
0.5392	Remote Similarity	NPC270667
0.5392	Remote Similarity	NPC1046
0.5392	Remote Similarity	NPC78046
0.5377	Remote Similarity	NPC80843
0.537	Remote Similarity	NPC11551
0.5364	Remote Similarity	NPC79718
0.5364	Remote Similarity	NPC64715
0.5361	Remote Similarity	NPC88744
0.5361	Remote Similarity	NPC283849
0.5357	Remote Similarity	NPC488564
0.5333	Remote Similarity	NPC58448
0.5327	Remote Similarity	NPC223301
0.5327	Remote Similarity	NPC171544
0.531	Remote Similarity	NPC187290
0.53	Remote Similarity	NPC471967
0.53	Remote Similarity	NPC256798
0.5287	Remote Similarity	NPC274330
0.5283	Remote Similarity	NPC488561
0.5278	Remote Similarity	NPC30735
0.5269	Remote Similarity	NPC230151
0.5268	Remote Similarity	NPC301449
0.5268	Remote Similarity	NPC324875
0.5268	Remote Similarity	NPC292677
0.5268	Remote Similarity	NPC601290
0.5263	Remote Similarity	NPC62725
0.5248	Remote Similarity	NPC607754
0.5238	Remote Similarity	NPC59804
0.5234	Remote Similarity	NPC161674
0.5225	Remote Similarity	NPC119794
0.5221	Remote Similarity	NPC480474
0.5196	Remote Similarity	NPC161434
0.5185	Remote Similarity	NPC242840
0.5185	Remote Similarity	NPC112352
0.5182	Remote Similarity	NPC148417
0.5182	Remote Similarity	NPC235438
0.5169	Remote Similarity	NPC482135
0.5146	Remote Similarity	NPC475472
0.5135	Remote Similarity	NPC31193
0.513	Remote Similarity	NPC11242
0.51	Remote Similarity	NPC286347
0.51	Remote Similarity	NPC110139
0.51	Remote Similarity	NPC108709
0.5098	Remote Similarity	NPC475633
0.5094	Remote Similarity	NPC56713
0.5093	Remote Similarity	NPC469946
0.5091	Remote Similarity	NPC10607
0.5091	Remote Similarity	NPC46665
0.5091	Remote Similarity	NPC480475
0.5088	Remote Similarity	NPC480473
0.5056	Remote Similarity	NPC51700
0.5056	Remote Similarity	NPC88716
0.5056	Remote Similarity	NPC68160
0.5052	Remote Similarity	NPC485585
0.5051	Remote Similarity	NPC485882
0.505	Remote Similarity	NPC242611
0.5047	Remote Similarity	NPC114441
0.5047	Remote Similarity	NPC473373
0.5045	Remote Similarity	NPC63159
0.5044	Remote Similarity	NPC104372

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473481 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5906
0.1-0.2	3146
0.2-0.3	84
0.3-0.4	13
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