NPASS Compound

Natural Product: NPC100639

Natural Product ID	NPC100639
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kalopanaxsaponin C
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-10-[(2S,3R,4S,5S)-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	Kalopanaxsaponin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1910841
PubChem CID	21626540
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 202212 0 0 0 0 0 0 0 0999 V2000 12.2384 2.9291 -3.1546 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0294 3.0054 -2.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1967 3.2156 -0.9922 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9491 3.3076 -0.4256 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4068 2.0973 0.0319 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1220 1.2582 -1.0220 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7280 1.0515 -1.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2662 0.2425 -0.0001 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8663 0.1124 0.0105 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4421 -0.5281 1.1376 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3947 -1.4546 0.9099 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1978 -1.4165 1.6526 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1241 -0.5316 2.5308 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1120 -2.3941 1.3729 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8012 -3.7558 1.2510 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2299 -3.9379 -0.1797 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9849 -4.2226 -1.0106 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8030 -3.4135 -0.4590 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3637 -2.1354 0.1182 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3089 -1.0684 0.2628 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1993 -0.1899 -0.6960 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7812 0.9395 -0.7360 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8090 0.6401 0.2713 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1800 0.3208 1.6114 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5614 -1.0541 1.4826 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2875 -1.3419 2.7149 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2081 -2.4990 2.5589 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5463 -2.1636 1.3352 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0094 1.2590 1.8875 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1238 0.2994 2.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5126 0.7618 2.5727 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9926 0.7530 1.1630 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9798 1.5683 0.3839 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6143 2.8430 1.1018 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 1.9571 -0.9929 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8309 2.6066 -0.9364 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7421 1.4865 -0.4426 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4208 1.0454 0.9332 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0402 1.9337 1.9979 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1467 -0.3054 1.1299 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6359 -1.2272 0.1942 O 0 0 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0 0 0 0 0 0 0 -11.1956 0.7927 2.5824 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9893 -0.0676 3.3417 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.8193 0.7807 4.2811 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6243 1.6672 3.5958 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0226 -0.8964 4.2002 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8172 -1.2608 3.3399 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2164 -1.2185 1.8611 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.2053 -2.1514 1.6054 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8232 -0.3225 3.5845 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7212 -2.0148 4.6219 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2849 3.4555 0.3936 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6795 -5.6824 -0.8885 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2822 -3.7937 -2.4273 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5153 -1.2419 1.9319 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6027 -1.8717 1.1444 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7541 -1.2172 -0.1886 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0469 -1.1732 -0.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3861 -3.2593 0.9951 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0223 -0.4003 2.9472 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2067 1.5255 1.1495 C 0 0 1 0 0 0 0 0 0 0 0 0 11.6164 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-0.1987 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2419 -3.6405 1.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4747 -0.5041 3.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3578 0.4512 1.0010 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5254 3.1689 1.4878 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7555 1.1286 -0.6987 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2089 0.3159 -1.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2349 2.6622 0.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 17.2909 0.9320 1.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6829 1.2553 2.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7387 2.6531 1.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 17.7684 1.2358 -0.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7397 0.8668 -2.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8377 2.3107 -2.4680 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5815 -0.1855 -2.8180 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6736 -1.1145 -2.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 17.5640 3.4693 -0.8525 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9500 1.0503 2.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1950 2.2769 2.9897 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 1 0 10 11 1 0 11 12 1 0 12 13 2 0 14 12 1 1 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 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 6 24 29 1 1 24 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 1 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 1 38 40 1 0 40 41 1 0 37 42 1 0 42 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 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 52 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 55 58 1 0 54 59 1 0 47 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 67 70 1 0 66 71 1 0 46 72 1 0 17 73 1 0 17 74 1 0 10 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 76 79 1 0 75 80 1 0 5 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 87 89 1 0 89 90 1 0 90 91 1 0 91 92 1 0 90 93 1 0 89 94 1 0 82 95 1 0 81 96 1 0 83 3 1 0 91 85 1 0 77 8 1 0 27 14 1 0 38 32 1 0 48 43 1 0 56 50 1 0 68 61 1 0 19 14 1 0 25 20 1 0 33 23 1 0 1 97 1 0 2 98 1 0 2 99 1 0 3100 1 6 5101 1 1 7102 1 0 7103 1 0 8104 1 1 10105 1 1 15106 1 0 15107 1 0 16108 1 0 16109 1 0 18110 1 0 18111 1 0 19112 1 6 21113 1 0 22114 1 0 22115 1 0 23116 1 6 26117 1 0 26118 1 0 27119 1 0 27120 1 0 28121 1 0 28122 1 0 28123 1 0 29124 1 0 29125 1 0 29126 1 0 30127 1 0 30128 1 0 31129 1 0 31130 1 0 32131 1 6 34132 1 0 34133 1 0 34134 1 0 35135 1 0 35136 1 0 36137 1 0 36138 1 0 37139 1 6 39140 1 0 39141 1 0 39142 1 0 40143 1 0 40144 1 0 41145 1 0 43146 1 6 45147 1 0 45148 1 0 46149 1 6 47150 1 6 48151 1 1 50152 1 1 52153 1 6 53154 1 0 53155 1 0 53156 1 0 54157 1 6 55158 1 1 56159 1 1 57160 1 0 58161 1 0 59162 1 0 61163 1 6 63164 1 6 64165 1 0 64166 1 0 65167 1 0 66168 1 1 67169 1 1 68170 1 6 69171 1 0 70172 1 0 71173 1 0 72174 1 0 73175 1 0 73176 1 0 73177 1 0 74178 1 0 74179 1 0 74180 1 0 75181 1 1 76182 1 1 77183 1 6 78184 1 0 79185 1 0 80186 1 0 81187 1 6 82188 1 1 83189 1 6 85190 1 6 87191 1 1 88192 1 0 88193 1 0 88194 1 0 89195 1 1 90196 1 6 91197 1 6 92198 1 0 93199 1 0 94200 1 0 95201 1 0 96202 1 0 M END

Standard InCHIKey	WPOFJVWZECLVLS-SLQVDRJLSA-N
Standard InCHI	InChI=1S/C65H106O31/c1-25-36(70)40(74)45(79)54(87-25)94-51-31(21-67)90-53(49(83)44(51)78)86-23-32-39(73)43(77)48(82)57(91-32)96-59(84)65-17-15-60(3,4)19-28(65)27-9-10-34-61(5)13-12-35(62(6,24-68)33(61)11-14-64(34,8)63(27,7)16-18-65)92-58-52(95-55-46(80)41(75)37(71)26(2)88-55)50(29(69)22-85-58)93-56-47(81)42(76)38(72)30(20-66)89-56/h9,25-26,28-58,66-83H,10-24H2,1-8H3/t25-,26-,28-,29-,30+,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-,56-,57-,58-,61-,62-,63+,64+,65-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@@]34CCC(C[C@H]4C4=CC[C@H]5[C@@]([C@@]4(CC3)C)(C)CC[C@@H]3[C@]5(C)CC[C@@H]([C@@]3(C)CO)O[C@@H]3OC[C@@H]([C@@H]([C@H]3O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)O)(C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1382.67	Volume:	1305.899 ? Van der Waals volume.
Dense:	1.059	LogP:	-0.004 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.916 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.109 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	63.0
TPSA:	491.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	31.0
H-Bond Donor:	18.0	Rings:	11.0
Heavy Atoms:	31.0

MedChem Properties

QED Drug-Likeness Score:	0.039	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.749	Fsp³:	0.954
MCE-18:	239.717 ? 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:	0.714	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.375	Promiscuous compounds:	0.069

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.33	MDCK Permeability:	-4.869
Pgp-inhibitor:	0.0	Pgp-substrate:	0.289
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):	0.974
20% Bioavailability (F20%):	0.255	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.001
Plasma Protein Binding (PPB):	57.352%	Volume Distribution (VD):	-0.219
Fu:	22.685% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.011
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.658
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):

-1.562

Half-life (T1/2):

5.855

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.499	Drug-induced Liver Injury (DILI):	0.917
AMES Toxicity:	0.981	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.432	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.086	RPMI-8226 Immunitoxicity:	0.573
A549 Cytotoxicity:	0.962	Hek293 Cytotoxicity:	0.598
BCF:	1.254 ? 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:	3.438 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.732 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.814 ? 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
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21870831]
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	stem bark	Purchased from an herbal market at Kumsan, Chungnam, Korea	2009-AUG	PMID[21870831]
NPO30412	Kalopanax pictus	Species	Araliaceae	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	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	3900.0	nM	PMID[21870831]

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 NPC100639 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	24098
0.1-0.2	21718
0.2-0.3	2682
0.3-0.4	837
0.4-0.5	323
0.5-0.6	107
0.6-0.7	47
0.7-0.8	0
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8972	High Similarity	NPC155410
0.8519	High Similarity	NPC76972
0.8519	High Similarity	NPC469782
0.8519	High Similarity	NPC204414
0.8148	Intermediate Similarity	NPC241909
0.8125	Intermediate Similarity	NPC135904
0.812	Intermediate Similarity	NPC298034
0.812	Intermediate Similarity	NPC71065
0.7949	Intermediate Similarity	NPC65105
0.7925	Intermediate Similarity	NPC46665
0.7857	Intermediate Similarity	NPC60557
0.7857	Intermediate Similarity	NPC67857
0.7788	Intermediate Similarity	NPC192600
0.7739	Intermediate Similarity	NPC475160
0.7739	Intermediate Similarity	NPC473714
0.7731	Intermediate Similarity	NPC202828
0.7731	Intermediate Similarity	NPC119592
0.7593	Intermediate Similarity	NPC102439
0.7583	Intermediate Similarity	NPC305981
0.7583	Intermediate Similarity	NPC481081
0.7521	Intermediate Similarity	NPC261506
0.7521	Intermediate Similarity	NPC4328
0.75	Intermediate Similarity	NPC295823
0.75	Intermediate Similarity	NPC174720
0.75	Intermediate Similarity	NPC104071
0.75	Intermediate Similarity	NPC475467
0.7417	Intermediate Similarity	NPC41061
0.7417	Intermediate Similarity	NPC227551
0.7417	Intermediate Similarity	NPC258617
0.7395	Intermediate Similarity	NPC476068
0.7355	Intermediate Similarity	NPC43550
0.7227	Intermediate Similarity	NPC488560
0.7222	Intermediate Similarity	NPC295371
0.7154	Intermediate Similarity	NPC236638
0.7154	Intermediate Similarity	NPC294453
0.7073	Intermediate Similarity	NPC293330
0.7063	Intermediate Similarity	NPC250247
0.7054	Intermediate Similarity	NPC63159
0.7025	Intermediate Similarity	NPC481080
0.7009	Intermediate Similarity	NPC48499
0.6903	Remote Similarity	NPC148417
0.6847	Remote Similarity	NPC161674
0.6833	Remote Similarity	NPC165204
0.6818	Remote Similarity	NPC473373
0.6786	Remote Similarity	NPC112352
0.6759	Remote Similarity	NPC29069
0.675	Remote Similarity	NPC79643
0.6609	Remote Similarity	NPC68175
0.6504	Remote Similarity	NPC123199
0.6462	Remote Similarity	NPC220160
0.6429	Remote Similarity	NPC57484
0.6404	Remote Similarity	NPC263756
0.6393	Remote Similarity	NPC475287
0.6387	Remote Similarity	NPC481079
0.6379	Remote Similarity	NPC101744
0.6345	Remote Similarity	NPC469775
0.6333	Remote Similarity	NPC469777
0.6328	Remote Similarity	NPC475514
0.6327	Remote Similarity	NPC469774
0.6293	Remote Similarity	NPC309714
0.6271	Remote Similarity	NPC475504
0.625	Remote Similarity	NPC110633
0.6239	Remote Similarity	NPC10607
0.6218	Remote Similarity	NPC134835
0.6209	Remote Similarity	NPC469772
0.62	Remote Similarity	NPC100925
0.6198	Remote Similarity	NPC80986
0.619	Remote Similarity	NPC470218
0.6186	Remote Similarity	NPC475591
0.6186	Remote Similarity	NPC236870
0.6148	Remote Similarity	NPC36831
0.6148	Remote Similarity	NPC187290
0.614	Remote Similarity	NPC235405
0.6129	Remote Similarity	NPC469773
0.6121	Remote Similarity	NPC473343
0.6119	Remote Similarity	NPC480417
0.6107	Remote Similarity	NPC136768
0.609	Remote Similarity	NPC224381
0.6087	Remote Similarity	NPC249848
0.6087	Remote Similarity	NPC107966
0.6063	Remote Similarity	NPC471550
0.605	Remote Similarity	NPC235438
0.6033	Remote Similarity	NPC73318
0.6016	Remote Similarity	NPC481078
0.6015	Remote Similarity	NPC70809
0.6	Remote Similarity	NPC475516
0.6	Remote Similarity	NPC268184
0.5983	Remote Similarity	NPC469946
0.5966	Remote Similarity	NPC473459
0.596	Remote Similarity	NPC469778
0.5935	Remote Similarity	NPC96641
0.5935	Remote Similarity	NPC163183
0.5926	Remote Similarity	NPC237503
0.5906	Remote Similarity	NPC469776
0.5906	Remote Similarity	NPC475899
0.5897	Remote Similarity	NPC473884
0.5894	Remote Similarity	NPC32723
0.5882	Remote Similarity	NPC109588
0.5882	Remote Similarity	NPC30735
0.5878	Remote Similarity	NPC473452
0.5868	Remote Similarity	NPC222580
0.5857	Remote Similarity	NPC475368
0.5855	Remote Similarity	NPC481323
0.5833	Remote Similarity	NPC251768
0.582	Remote Similarity	NPC601659
0.5812	Remote Similarity	NPC150400
0.5796	Remote Similarity	NPC295941
0.5789	Remote Similarity	NPC214484
0.5779	Remote Similarity	NPC135334
0.5763	Remote Similarity	NPC39211
0.575	Remote Similarity	NPC117714
0.5742	Remote Similarity	NPC481324
0.5741	Remote Similarity	NPC167383
0.5738	Remote Similarity	NPC297263
0.5683	Remote Similarity	NPC480422
0.5667	Remote Similarity	NPC192791
0.5664	Remote Similarity	NPC256798
0.5645	Remote Similarity	NPC114484
0.5635	Remote Similarity	NPC31838
0.562	Remote Similarity	NPC160415
0.56	Remote Similarity	NPC301449
0.56	Remote Similarity	NPC601290
0.5583	Remote Similarity	NPC76497
0.5583	Remote Similarity	NPC213674
0.5574	Remote Similarity	NPC480475
0.5537	Remote Similarity	NPC223301
0.5537	Remote Similarity	NPC171544
0.553	Remote Similarity	NPC47995
0.552	Remote Similarity	NPC281148
0.552	Remote Similarity	NPC104372
0.5517	Remote Similarity	NPC90856
0.5496	Remote Similarity	NPC475209
0.5478	Remote Similarity	NPC209894
0.5447	Remote Similarity	NPC40775
0.5447	Remote Similarity	NPC473401
0.5447	Remote Similarity	NPC173859
0.5447	Remote Similarity	NPC148603
0.5441	Remote Similarity	NPC161717
0.5433	Remote Similarity	NPC187618
0.5424	Remote Similarity	NPC475208
0.542	Remote Similarity	NPC133818
0.5407	Remote Similarity	NPC286457
0.5385	Remote Similarity	NPC189884
0.5385	Remote Similarity	NPC138334
0.5379	Remote Similarity	NPC480419
0.5378	Remote Similarity	NPC136877
0.5372	Remote Similarity	NPC157868
0.5366	Remote Similarity	NPC471548
0.536	Remote Similarity	NPC609763
0.5333	Remote Similarity	NPC139894
0.5328	Remote Similarity	NPC471385
0.5328	Remote Similarity	NPC471547
0.5323	Remote Similarity	NPC159309
0.5323	Remote Similarity	NPC164389
0.5323	Remote Similarity	NPC86222
0.5312	Remote Similarity	NPC480474
0.531	Remote Similarity	NPC199457
0.5294	Remote Similarity	NPC480418
0.529	Remote Similarity	NPC477463
0.5285	Remote Similarity	NPC242840
0.528	Remote Similarity	NPC139044
0.5263	Remote Similarity	NPC68419
0.5255	Remote Similarity	NPC470876
0.5252	Remote Similarity	NPC302543
0.5235	Remote Similarity	NPC472268
0.5211	Remote Similarity	NPC102505
0.5211	Remote Similarity	NPC488514
0.52	Remote Similarity	NPC11551
0.5197	Remote Similarity	NPC469821
0.5194	Remote Similarity	NPC480473
0.5175	Remote Similarity	NPC306746
0.5168	Remote Similarity	NPC297950
0.5164	Remote Similarity	NPC173583
0.5159	Remote Similarity	NPC162574
0.5154	Remote Similarity	NPC104137
0.5154	Remote Similarity	NPC26626
0.5154	Remote Similarity	NPC473826
0.5152	Remote Similarity	NPC313110
0.5143	Remote Similarity	NPC309223
0.5128	Remote Similarity	NPC128925
0.5122	Remote Similarity	NPC470512
0.5115	Remote Similarity	NPC470915
0.5113	Remote Similarity	NPC123522
0.5111	Remote Similarity	NPC283417
0.5111	Remote Similarity	NPC200049
0.5111	Remote Similarity	NPC191827
0.5096	Remote Similarity	NPC472269
0.5079	Remote Similarity	NPC305267
0.5078	Remote Similarity	NPC486563
0.5074	Remote Similarity	NPC54636
0.5072	Remote Similarity	NPC13998
0.5039	Remote Similarity	NPC114692
0.5037	Remote Similarity	NPC251263
0.5036	Remote Similarity	NPC85154

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC100639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7676
0.1-0.2	1415
0.2-0.3	52
0.3-0.4	7
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