NPASS Compound

Natural Product: NPC75318

Natural Product ID	NPC75318
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-[Alpha-L-Arabinopyranosyl(1_>6)]-2-Acetamido-2-Deoxy-Beta-D-Glucopyranosyl Echinocystic Acid
IUPAC Name	(4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1765595
PubChem CID	14217288
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 126132 0 0 0 0 0 0 0 0999 V2000 4.9167 -4.5860 1.2955 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8747 -3.5553 2.3612 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9076 -2.2998 2.0911 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9868 -1.8042 0.7483 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1885 -0.5537 0.5084 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0095 0.4069 -0.1363 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9366 0.7846 0.8328 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9749 -0.2971 0.9311 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4332 -1.5676 0.3184 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4290 -1.4058 -1.0630 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4103 -0.5034 2.2372 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5314 2.1440 0.5342 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1673 2.0993 -0.6873 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6996 3.3687 -0.9287 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2071 3.8039 -2.1558 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1670 2.6826 -2.9910 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4848 1.9853 -3.0825 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6077 2.7033 -2.3958 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2056 3.2772 -1.0570 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6879 4.6026 -0.9633 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6259 1.7595 -2.1536 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3869 0.6623 -2.6181 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0503 -0.8076 -0.2118 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8668 -0.3744 0.4367 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3131 0.7114 -0.4143 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1613 0.9384 -0.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9306 -0.3952 -0.4756 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4608 -1.2033 0.6729 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9936 -1.5541 0.6888 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2764 -2.0071 2.1251 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3263 -2.7390 -0.1919 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3325 -2.4108 0.9689 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6591 -1.7960 1.4461 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2546 -1.1254 0.2332 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3884 -0.1219 -0.4184 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0050 0.1830 -1.7635 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4750 0.2337 -1.6593 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2150 0.0001 -0.5872 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5168 -0.3578 0.6737 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1782 0.8646 1.4738 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3775 -1.2645 1.5036 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7603 -0.8088 1.7098 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4167 -0.0273 0.6177 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7170 0.1073 -0.6662 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9434 1.4065 -1.4052 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2638 2.0531 -1.2121 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2687 1.6762 -2.2991 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0571 3.5679 -1.4154 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8089 1.9033 0.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7328 1.4013 1.1103 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7525 -0.6305 0.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0405 -1.1125 -0.7041 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6572 -0.6458 1.4269 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9039 -0.0487 2.8999 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7592 -2.2318 -0.6660 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5022 -0.8803 -1.8281 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7977 -3.9798 3.6785 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8157 -4.4910 0.6537 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9342 -5.6003 1.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0447 -4.4989 0.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6150 -2.6199 0.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9415 -0.0583 1.4851 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3937 0.8976 1.8118 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8672 -0.0002 0.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0609 -2.4434 0.5611 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6323 -1.7923 -1.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4648 -1.4466 2.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1952 2.4799 1.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7043 2.8709 0.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4811 4.0766 -0.0981 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7802 2.9803 -3.9779 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4239 1.9814 -2.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7637 1.8971 -4.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0345 3.4954 -3.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6303 2.6967 -0.2036 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7307 4.8000 0.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4879 1.2982 -1.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2588 0.2203 -2.5920 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2364 0.0735 1.4067 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6544 0.6192 -1.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7962 1.6778 -0.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3817 1.3274 0.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4521 1.6536 -1.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5962 -0.5426 1.5884 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4607 -1.7415 2.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2378 -1.5906 2.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3728 -3.1093 2.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1706 -2.5277 -0.8881 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6864 -3.6315 0.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4237 -3.1358 -0.7264 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9190 -2.9301 1.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4716 -3.0735 0.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3413 -2.5997 1.7565 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4114 -1.0797 2.2285 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5047 0.8399 0.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6902 1.2378 -2.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6572 -0.5237 -2.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9916 0.4979 -2.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9720 1.0896 2.2465 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2434 0.7718 2.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1747 1.7982 0.8366 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3734 -2.3169 1.1235 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8784 -1.3394 2.5148 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3686 -1.7343 1.9598 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1131 -0.7001 -1.3531 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1440 2.1604 -1.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8672 1.1950 -2.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9665 0.6963 -2.7737 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3064 1.6364 -1.9050 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2778 2.4001 -3.1398 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7437 3.6679 -2.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3035 3.9463 -0.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0390 4.0804 -1.3555 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6963 1.2700 0.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1581 2.8725 0.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8550 2.0486 1.0083 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0724 1.3915 2.1457 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5609 -1.0998 1.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3478 -0.4011 3.6216 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5013 -3.2363 -0.2495 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8509 -2.1775 -0.8619 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2946 -2.2329 -1.6734 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6912 -0.0197 -2.5384 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5787 -1.0595 -1.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0240 -1.7343 -2.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4388 -3.3897 4.4235 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 1 0 8 11 1 0 7 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 18 21 1 0 17 22 1 0 5 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 28 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 1 1 39 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 46 48 1 0 46 49 1 0 49 50 1 0 43 51 1 6 51 52 2 0 51 53 1 0 42 54 1 0 34 55 1 6 27 56 1 6 2 57 1 0 9 4 1 0 19 14 1 0 29 24 1 0 39 34 1 0 50 43 1 0 35 27 1 0 44 38 1 0 1 58 1 0 1 59 1 0 1 60 1 0 4 61 1 6 5 62 1 1 7 63 1 1 8 64 1 6 9 65 1 6 10 66 1 0 11 67 1 0 12 68 1 0 12 69 1 0 14 70 1 1 16 71 1 0 16 72 1 0 17 73 1 6 18 74 1 6 19 75 1 1 20 76 1 0 21 77 1 0 22 78 1 0 24 79 1 1 25 80 1 0 25 81 1 0 26 82 1 0 26 83 1 0 28 84 1 1 30 85 1 0 30 86 1 0 30 87 1 0 31 88 1 0 31 89 1 0 31 90 1 0 32 91 1 0 32 92 1 0 33 93 1 0 33 94 1 0 35 95 1 1 36 96 1 0 36 97 1 0 37 98 1 0 40 99 1 0 40100 1 0 40101 1 0 41102 1 0 41103 1 0 42104 1 1 44105 1 6 45106 1 0 45107 1 0 47108 1 0 47109 1 0 47110 1 0 48111 1 0 48112 1 0 48113 1 0 49114 1 0 49115 1 0 50116 1 0 50117 1 0 53118 1 0 54119 1 0 55120 1 0 55121 1 0 55122 1 0 56123 1 0 56124 1 0 56125 1 0 57126 1 0 M END

Standard InCHIKey	LRMCXUYYLPHGOS-CJXDOCFZSA-N
Standard InCHI	InChI=1S/C43H69NO13/c1-21(45)44-30-33(50)32(49)25(20-55-36-34(51)31(48)24(46)19-54-36)56-35(30)57-29-12-13-40(6)26(39(29,4)5)11-14-41(7)27(40)10-9-22-23-17-38(2,3)15-16-43(23,37(52)53)28(47)18-42(22,41)8/h9,23-36,46-51H,10-20H2,1-8H3,(H,44,45)(H,52,53)/t23-,24-,25+,26-,27+,28+,29-,30+,31-,32+,33+,34+,35-,36-,40-,41+,42+,43+/m0/s1
SMILES	CC(=N[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)C[C@H]([C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)O)C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	807.48	Volume:	809.749 ? Van der Waals volume.
Dense:	0.997	LogP:	1.887 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.516 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.506 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	40.0
TPSA:	228.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.08	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.088	Fsp³:	0.907
MCE-18:	152.976 ? 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:	0.935	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.014	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.818	MDCK Permeability:	-5.195
Pgp-inhibitor:	0.0	Pgp-substrate:	0.04
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):	0.309
20% Bioavailability (F20%):	0.575	30% Bioavailability (F30%):	0.971
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015	MRP1:	0.152
Plasma Protein Binding (PPB):	76.401%	Volume Distribution (VD):	-0.473
Fu:	16.888% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.02
BSEP inhibitor:	0.005

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:	0.996	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.498
HLM stability:	0.001 ? 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):

0.286

Half-life (T1/2):

2.301

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.996	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.892	Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.019	Skin Sensitization:	1.0
Carcinogencity:	0.574	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.171
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.97
Hematotoxicity:	0.718	Drug-induced Nephrotoxicity:	0.959
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.051
A549 Cytotoxicity:	0.515	Hek293 Cytotoxicity:	0.313
BCF:	1.11 ? 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:	3.997 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.849 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.887 ? 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
NPO17211	Albizia inundata	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21314099]
NPO17211	Albizia inundata	Species	Fabaceae	Eukaryota	aerial parts	Primavera, Department Patino, Province of Formosa, Argentina (lat. 27S, long. 58W)	1999-AUG	PMID[21314099]
NPO17211	Albizia inundata	Species	Fabaceae	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	4

Activity Type	# Activity
Cell line	2
Non-molecular	2

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
NPT169	Cell line	B16-F10	Mus musculus	IC50	=	5100.0	nM	PMID[21314099]
NPT170	Cell line	SK-MEL-28	Homo sapiens	IC50	=	9200.0	nM	PMID[21314099]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2800.0	nM	PMID[21314099]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1800.0	nM	PMID[21314099]

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 NPC75318 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	21650
0.1-0.2	24123
0.2-0.3	2919
0.3-0.4	840
0.4-0.5	250
0.5-0.6	44
0.6-0.7	16
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8687	High Similarity	NPC145899
0.8485	Intermediate Similarity	NPC73829
0.8061	Intermediate Similarity	NPC488516
0.785	Intermediate Similarity	NPC200788
0.7706	Intermediate Similarity	NPC243680
0.7664	Intermediate Similarity	NPC280941
0.7664	Intermediate Similarity	NPC235772
0.7579	Intermediate Similarity	NPC242611
0.7551	Intermediate Similarity	NPC76999
0.7524	Intermediate Similarity	NPC119794
0.7431	Intermediate Similarity	NPC288205
0.7431	Intermediate Similarity	NPC51465
0.7358	Intermediate Similarity	NPC488515
0.7255	Intermediate Similarity	NPC480424
0.7064	Intermediate Similarity	NPC291903
0.6952	Remote Similarity	NPC80843
0.672	Remote Similarity	NPC120667
0.672	Remote Similarity	NPC278272
0.66	Remote Similarity	NPC31839
0.6522	Remote Similarity	NPC475119
0.6466	Remote Similarity	NPC473824
0.6348	Remote Similarity	NPC475486
0.6346	Remote Similarity	NPC191410
0.6239	Remote Similarity	NPC488561
0.6238	Remote Similarity	NPC283849
0.6228	Remote Similarity	NPC37134
0.6161	Remote Similarity	NPC104400
0.6161	Remote Similarity	NPC10320
0.6154	Remote Similarity	NPC210729
0.6154	Remote Similarity	NPC82931
0.6102	Remote Similarity	NPC172365
0.5982	Remote Similarity	NPC469945
0.5856	Remote Similarity	NPC127056
0.5776	Remote Similarity	NPC481082
0.5776	Remote Similarity	NPC164419
0.5766	Remote Similarity	NPC56713
0.5726	Remote Similarity	NPC79718
0.57	Remote Similarity	NPC601365
0.5645	Remote Similarity	NPC166422
0.5619	Remote Similarity	NPC28198
0.5619	Remote Similarity	NPC476123
0.56	Remote Similarity	NPC475140
0.5526	Remote Similarity	NPC6377
0.5526	Remote Similarity	NPC208381
0.552	Remote Similarity	NPC219180
0.5508	Remote Similarity	NPC257468
0.5495	Remote Similarity	NPC164194
0.5472	Remote Similarity	NPC606107
0.5463	Remote Similarity	NPC100383
0.5462	Remote Similarity	NPC484832
0.5398	Remote Similarity	NPC136877
0.5372	Remote Similarity	NPC324875
0.5372	Remote Similarity	NPC292677
0.5351	Remote Similarity	NPC25605
0.5351	Remote Similarity	NPC59804
0.5328	Remote Similarity	NPC488564
0.5259	Remote Similarity	NPC472949
0.5253	Remote Similarity	NPC228784
0.5253	Remote Similarity	NPC324341
0.5253	Remote Similarity	NPC601810
0.5225	Remote Similarity	NPC284807
0.5217	Remote Similarity	NPC174679
0.5217	Remote Similarity	NPC279554
0.5214	Remote Similarity	NPC22956
0.5197	Remote Similarity	NPC323341
0.5185	Remote Similarity	NPC482010
0.5172	Remote Similarity	NPC109079
0.5126	Remote Similarity	NPC114304
0.512	Remote Similarity	NPC62725
0.5113	Remote Similarity	NPC161717
0.5091	Remote Similarity	NPC286347
0.5081	Remote Similarity	NPC488209
0.5041	Remote Similarity	NPC139044
0.504	Remote Similarity	NPC207738
0.5039	Remote Similarity	NPC251263

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC75318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6252
0.1-0.2	2832
0.2-0.3	62
0.3-0.4	3
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