NPASS Compound

Natural Product: NPC470517

Natural Product ID	NPC470517
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sorbifoliaside F
IUPAC Name	[(2R,3R,4R,5R,6R)-2-[[(3S,4aR,6aR,6bS,8aR,9R,10R,12aS,14aR,14bR)-8a-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-9,10-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-acetyloxy-3-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms	sorbifoliaside F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2058432
PubChem CID	66552845
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 206215 0 0 0 0 0 0 0 0999 V2000 11.3183 2.9542 0.2829 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2575 3.6306 -0.5963 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2688 3.4839 -1.8972 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3383 4.2773 -2.6695 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3433 2.6928 -2.6787 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5337 2.6361 -3.9458 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2665 1.9759 -2.2923 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3664 1.2003 -2.9788 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9426 1.6506 -2.9382 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4971 1.8280 -1.4208 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2893 1.0146 -0.6532 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4632 -0.2491 -1.1939 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3336 -0.2527 -2.4219 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5908 -0.8034 -2.2712 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0296 -1.8538 -3.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2609 -2.2948 -3.9555 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3942 -2.4063 -2.8560 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7445 -1.2729 -0.1736 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8872 -1.0724 0.5862 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1401 -2.1062 1.4647 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1863 -1.8294 2.9057 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5764 -2.1514 3.4181 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5651 -1.4392 2.5194 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4323 -1.9523 1.0923 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2858 -2.7441 0.9923 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5955 -2.8897 0.8387 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8200 -2.1859 0.9185 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8359 -1.7776 2.9683 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7999 -3.5007 3.4716 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3182 -2.6622 3.6481 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2602 1.6483 -1.2560 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0412 1.9242 -1.2540 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6212 2.6064 0.0991 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1682 2.7921 0.1882 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3576 1.4771 0.1239 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7598 0.8501 -1.1362 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1988 0.7114 -1.4591 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3162 0.1219 -2.8547 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7226 -0.4432 -0.5695 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1338 1.5871 -2.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6438 1.4626 -2.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0160 1.5269 -0.9860 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8853 1.7246 0.2109 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2938 1.0974 1.4359 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2294 1.1447 1.4868 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8863 0.8219 0.4081 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0334 0.4464 -0.7805 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0551 0.5523 -1.9378 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0133 -0.5796 -1.6995 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8893 -0.3178 -0.4869 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3573 0.8031 0.3504 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9532 0.8711 1.7066 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0714 -0.4024 2.4379 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5752 -1.6113 1.6901 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0595 -1.5957 0.3035 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6113 -2.6644 -0.4797 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2722 -1.9121 1.9461 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3003 -0.3535 3.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5209 -0.6672 2.8688 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2635 -0.0114 -1.0320 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2631 0.2092 -0.0979 O 0 0 0 0 0 0 0 0 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0 0 0 0 0 0 0 0 0 0 0 0 14.3040 3.8094 -2.5313 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3408 5.3424 -2.2844 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9760 4.3226 -3.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6891 1.1267 -4.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2431 0.9024 -3.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8073 2.8674 -1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4241 -0.4925 -1.5858 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7958 -0.8019 -3.2264 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3597 -3.2594 -2.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0557 -1.6447 -2.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7852 -2.8148 -3.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8398 -1.4254 0.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9006 -2.3103 -0.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2994 -2.8567 1.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0227 -0.7569 3.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6733 -1.6376 4.4165 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3934 -0.3392 2.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4791 -1.1485 0.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6513 -3.6808 1.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5404 -3.4565 -0.0860 H 0 0 0 0 0 0 0 0 0 0 0 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0.9243 -1.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6434 -0.8720 -1.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2311 0.2078 -1.9074 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1537 1.5052 -0.9858 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5737 -0.9200 0.5983 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0812 -0.4353 -2.3610 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0965 -1.4665 -2.7372 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2648 -3.5901 -2.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6314 -3.7311 -1.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7096 -5.5888 -0.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2519 -4.8564 -1.1018 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8012 -6.3418 1.3317 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7706 -3.6955 2.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9058 -3.1112 1.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8900 -4.1443 3.7686 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1035 -2.8791 2.7580 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3833 -1.6431 3.9140 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3696 -4.8289 4.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9036 -4.5506 -0.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2055 -7.2716 0.0562 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1236 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0 0 0 0 0 0 0 0 0 0 2.4892 1.5184 2.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5682 3.3961 -3.6964 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 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 12 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 23 28 1 0 22 29 1 0 21 30 1 0 10 31 1 0 31 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 1 0 37 39 1 0 36 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 53 59 1 0 50 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 66 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 74 76 1 0 76 77 1 0 73 78 1 0 72 79 1 0 71 80 1 0 65 81 1 0 64 82 1 0 63 83 1 0 83 84 1 0 84 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 88 89 1 0 88 90 1 0 90 91 1 0 87 92 1 0 86 93 1 0 85 94 1 0 47 95 1 0 42 96 1 0 35 97 1 0 9 98 1 0 13 8 1 0 89 84 1 0 25 20 1 0 37 32 1 0 43 35 1 0 47 42 1 0 51 46 1 0 55 50 1 0 67 62 1 0 75 70 1 0 1 99 1 0 1100 1 0 1101 1 0 2102 1 0 4103 1 0 4104 1 0 4105 1 0 8106 1 0 9107 1 0 10108 1 0 12109 1 0 13110 1 0 17111 1 0 17112 1 0 17113 1 0 18114 1 0 18115 1 0 20116 1 0 21117 1 0 22118 1 0 23119 1 0 24120 1 0 26121 1 0 26122 1 0 27123 1 0 28124 1 0 29125 1 0 30126 1 0 32127 1 0 33128 1 0 33129 1 0 34130 1 0 34131 1 0 36132 1 0 38133 1 0 38134 1 0 38135 1 0 39136 1 0 39137 1 0 39138 1 0 40139 1 0 40140 1 0 41141 1 0 41142 1 0 43143 1 0 44144 1 0 44145 1 0 45146 1 0 48147 1 0 48148 1 0 49149 1 0 49150 1 0 51151 1 0 52152 1 0 52153 1 0 54154 1 0 55155 1 0 56156 1 0 57157 1 0 58158 1 0 58159 1 0 58160 1 0 59161 1 0 59162 1 0 59163 1 0 60164 1 0 60165 1 0 62166 1 0 63167 1 0 64168 1 0 65169 1 0 66170 1 0 68171 1 0 68172 1 0 70173 1 0 71174 1 0 72175 1 0 73176 1 0 74177 1 0 76178 1 0 76179 1 0 77180 1 0 78181 1 0 79182 1 0 80183 1 0 81184 1 0 82185 1 0 84186 1 0 85187 1 0 86188 1 0 87189 1 0 88190 1 0 90191 1 0 90192 1 0 91193 1 0 92194 1 0 93195 1 0 94196 1 0 95197 1 0 95198 1 0 95199 1 0 96200 1 0 96201 1 0 96202 1 0 97203 1 0 97204 1 0 97205 1 0 98206 1 0 M END

Standard InCHIKey	YQPIHQHVTWOTDZ-GFDWXXGQSA-N
Standard InCHI	InChI=1S/C67H108O31/c1-11-27(2)56(86)97-52-50(83)60(95-35(51(52)90-28(3)71)25-88-58-48(81)44(77)40(73)32(22-69)92-58)96-38-15-16-64(8)36(63(38,6)7)14-17-66(10)37(64)13-12-29-30-20-62(4,5)54(84)55(85)67(30,19-18-65(29,66)9)26-89-61-53(98-59-49(82)45(78)41(74)33(23-70)93-59)46(79)42(75)34(94-61)24-87-57-47(80)43(76)39(72)31(21-68)91-57/h11-12,30-55,57-61,68-70,72-85H,13-26H2,1-10H3/b27-11-/t30-,31+,32+,33+,34+,35+,36-,37+,38-,39+,40+,41+,42+,43-,44-,45-,46-,47+,48+,49+,50+,51+,52+,53+,54-,55-,57+,58+,59-,60-,61+,64-,65+,66+,67-/m0/s1
SMILES	CC=C(C)C(=O)OC1C(C(OC(C1OC(=O)C)COC2C(C(C(C(O2)CO)O)O)O)OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(C(C7O)O)(C)C)COC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1408.69	Volume:	1343.774 ? Van der Waals volume.
Dense:	1.048	LogP:	-0.777 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.575 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.958 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	21.0	Rigid Bonds:	59.0
TPSA:	488.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	31.0
H-Bond Donor:	17.0	Rings:	10.0
Heavy Atoms:	31.0

MedChem Properties

QED Drug-Likeness Score:	0.026	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.823	Fsp³:	0.91
MCE-18:	224.359 ? 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:	0.003	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.343 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.398	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.9	MDCK Permeability:	-5.033
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	1.0
20% Bioavailability (F20%):	0.981	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	36.081%	Volume Distribution (VD):	-0.323
Fu:	27.42% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.002	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.99	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.961	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):

-0.69

Half-life (T1/2):

3.886

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.23
Human Hepatotoxicity (H-HT):	0.212	Drug-induced Liver Injury (DILI):	0.248
AMES Toxicity:	0.586	Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.103	Skin Sensitization:	0.026
Carcinogencity:	0.003	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.358	Ototoxicity:	1.0
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.003
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.105
A549 Cytotoxicity:	0.029	Hek293 Cytotoxicity:	0.957
BCF:	0.157 ? 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:	4.215 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.632 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.276 ? 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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	10

Activity Type	# Activity
Cell line	8
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
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[21641210]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	>	100000.0	nM	PMID[1965654]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	DrugMatrix in vivo data: Biochemistry
NPT306	Cell line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[23317013]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[16872131]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[24904961]
NPT453	Cell line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[22119124]
NPT1171	Cell line	HEp-2	Homo sapiens	IC50	>	100000.0	nM	PMID[11374974]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[22801644]

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 NPC470517 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	22850
0.1-0.2	22726
0.2-0.3	3108
0.3-0.4	652
0.4-0.5	458
0.5-0.6	47
0.6-0.7	3
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8198	Intermediate Similarity	NPC470911
0.8	Intermediate Similarity	NPC470915
0.7885	Intermediate Similarity	NPC470512
0.7593	Intermediate Similarity	NPC173859
0.7523	Intermediate Similarity	NPC470515
0.7273	Intermediate Similarity	NPC148603
0.6696	Remote Similarity	NPC470513
0.6333	Remote Similarity	NPC470516
0.6271	Remote Similarity	NPC470514
0.5902	Remote Similarity	NPC470914
0.5854	Remote Similarity	NPC481079
0.5794	Remote Similarity	NPC185466
0.5565	Remote Similarity	NPC471435
0.5565	Remote Similarity	NPC471434
0.5556	Remote Similarity	NPC48499
0.5528	Remote Similarity	NPC63159
0.5448	Remote Similarity	NPC470518
0.5391	Remote Similarity	NPC207738
0.5385	Remote Similarity	NPC610204
0.5379	Remote Similarity	NPC603137
0.5267	Remote Similarity	NPC607904
0.5255	Remote Similarity	NPC271610
0.5252	Remote Similarity	NPC141600
0.5232	Remote Similarity	NPC220838
0.5231	Remote Similarity	NPC606553
0.5227	Remote Similarity	NPC79643
0.5182	Remote Similarity	NPC265841
0.5166	Remote Similarity	NPC45606
0.5166	Remote Similarity	NPC329878
0.5154	Remote Similarity	NPC609281
0.5149	Remote Similarity	NPC135904
0.5147	Remote Similarity	NPC244296
0.5143	Remote Similarity	NPC11577
0.5118	Remote Similarity	NPC222580
0.5118	Remote Similarity	NPC470913
0.5118	Remote Similarity	NPC123796
0.5113	Remote Similarity	NPC123522
0.5111	Remote Similarity	NPC475140
0.5109	Remote Similarity	NPC484061
0.5109	Remote Similarity	NPC484062
0.5108	Remote Similarity	NPC43550
0.5081	Remote Similarity	NPC76497
0.5081	Remote Similarity	NPC469946
0.5079	Remote Similarity	NPC480475
0.504	Remote Similarity	NPC112352
0.5039	Remote Similarity	NPC148417
0.5038	Remote Similarity	NPC104137
0.5038	Remote Similarity	NPC26626
0.5038	Remote Similarity	NPC610461
0.5037	Remote Similarity	NPC123199
0.5037	Remote Similarity	NPC609305
0.5036	Remote Similarity	NPC71391
0.5036	Remote Similarity	NPC41061
0.5036	Remote Similarity	NPC227551
0.5036	Remote Similarity	NPC82380
0.5033	Remote Similarity	NPC329893

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7609
0.1-0.2	1491
0.2-0.3	44
0.3-0.4	6
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data