NPASS Compound

Natural Product: NPC316841

Natural Product ID	NPC316841
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CAEARXJBKWWZOC-VWBQBHFSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1813071
PubChem CID	56683154
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

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 118124 0 0 0 0 0 0 0 0999 V2000 -0.2805 4.5379 -4.4032 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1042 3.9775 -3.0172 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3421 4.6675 -2.0090 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3088 2.7326 -2.8910 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5947 1.7891 -1.9486 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5079 1.1045 -1.1858 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3476 0.4713 -2.2711 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7351 0.4573 -1.9959 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6916 1.0708 -2.7811 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2942 1.6789 -3.8077 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1556 1.0288 -2.4446 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9700 -0.8641 -2.7726 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1675 -1.5917 -3.0989 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3893 -2.0753 -4.3750 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5260 -1.8739 -5.2685 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6046 -2.8261 -4.7464 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2098 -1.7661 -1.8545 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7042 -1.2648 -0.4787 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1287 -0.0432 -0.3451 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3257 -0.2924 -1.0193 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2262 -1.4447 -1.7242 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9730 -1.4718 -3.0674 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0524 -2.4456 -0.8965 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3244 -1.7607 -0.8485 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3651 -2.3716 -0.2197 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1645 -3.4979 0.2918 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7269 -1.8631 -0.0693 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6591 -2.5971 -0.8144 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9734 -2.2572 -0.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4005 -1.1843 -0.0494 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4714 -0.5171 0.6447 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1565 -0.8148 0.6636 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2811 0.0251 1.5308 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2188 1.4697 1.0983 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3969 2.2687 2.0490 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9843 1.9263 2.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 1.3958 3.2603 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0328 2.1224 1.2133 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6487 1.7533 1.3942 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3386 2.6334 0.8006 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1837 2.0759 -0.3187 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3170 1.5441 0.3990 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5487 2.1496 0.3731 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6556 3.2227 -0.3191 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7358 1.6991 1.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9254 2.3807 0.9680 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0723 1.9235 1.6248 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0077 0.7599 2.3687 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8287 0.0706 2.4548 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7056 0.5468 1.7934 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1680 3.2112 1.8119 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2255 4.5327 2.1330 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5110 5.3362 1.5175 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1600 4.9581 3.2266 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4613 0.3004 1.0415 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3994 -0.2913 2.1350 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7353 -0.2583 1.4017 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0716 2.1431 3.4233 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5093 -2.3297 0.3462 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5600 -3.0342 0.8958 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -2.6726 0.6179 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3073 -4.1562 1.7660 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3836 -4.8452 2.2888 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1893 -5.9267 3.1300 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9275 -6.3366 3.4616 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1524 -5.6730 2.9586 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0512 -4.5798 2.1081 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7207 4.6024 -4.8504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8374 5.4760 -4.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 3.7666 -4.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2721 2.3588 -1.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2924 1.0701 -2.4309 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3048 1.1137 -3.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3091 0.4065 -1.5405 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7122 0.5279 -3.2712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5493 2.0368 -2.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4058 -0.8354 -3.7291 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3802 -3.8550 -5.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2875 -2.9339 -3.8810 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1391 -2.2263 -5.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4577 -2.8062 -2.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7999 -1.0819 -0.5682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0668 -1.2513 -2.8840 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9714 -2.4969 -3.4955 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5736 -0.8086 -3.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7097 -2.6239 0.0964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1466 -3.3902 -1.4507 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2635 -3.4536 -1.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6836 -2.8416 -1.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4417 -0.8924 -0.0223 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2947 -0.4661 1.5044 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6359 -0.0480 2.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7278 1.4692 0.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2404 1.8829 1.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4458 3.3677 1.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5569 1.8835 2.5273 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2090 3.5337 0.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6215 2.9499 -0.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0445 3.2995 0.4026 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0128 2.4677 1.5605 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9011 0.3852 2.8914 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8174 -0.8347 3.0467 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8003 -0.0045 1.8727 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6636 5.5996 3.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6445 4.0974 3.6860 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9458 5.5819 2.7407 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0429 -1.2092 2.6030 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4541 -0.3773 1.9303 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3497 0.4194 3.0193 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6672 -1.0723 1.9050 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6094 1.3173 4.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1693 2.0363 3.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8910 3.0834 3.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4091 -4.5702 2.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0624 -6.4458 3.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8009 -7.1872 4.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1739 -5.9728 3.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8234 -4.0862 1.7360 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 6 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 7 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 40 51 1 0 51 52 1 0 52 53 2 0 52 54 1 0 39 55 1 0 55 56 1 0 55 57 1 1 35 58 1 0 18 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 62 63 2 0 63 64 1 0 64 65 2 0 65 66 1 0 66 67 2 0 41 6 1 0 50 45 1 0 67 62 1 0 19 6 1 0 32 27 1 0 21 17 1 0 55 19 1 0 1 68 1 0 1 69 1 0 1 70 1 0 5 71 1 0 5 72 1 0 7 73 1 6 11 74 1 0 11 75 1 0 11 76 1 0 12 77 1 6 16 78 1 0 16 79 1 0 16 80 1 0 17 81 1 6 18 82 1 6 22 83 1 0 22 84 1 0 22 85 1 0 23 86 1 0 23 87 1 0 28 88 1 0 29 89 1 0 30 90 1 0 33 91 1 0 33 92 1 0 34 93 1 0 34 94 1 0 35 95 1 6 39 96 1 1 40 97 1 6 41 98 1 6 46 99 1 0 47100 1 0 48101 1 0 49102 1 0 50103 1 0 54104 1 0 54105 1 0 54106 1 0 56107 1 0 56108 1 0 56109 1 0 57110 1 0 58111 1 0 58112 1 0 58113 1 0 63114 1 0 64115 1 0 65116 1 0 66117 1 0 67118 1 0 M END

Standard InCHIKey	CAEARXJBKWWZOC-VWBQBHFSSA-N
Standard InCHI	InChI=1S/C48H51NO18/c1-25-20-21-33-32(19-14-22-49-33)44(57)60-23-45(6)34-35(61-27(3)51)39(63-29(5)53)47(24-59-26(2)50)40(66-43(56)31-17-12-9-13-18-31)36(62-28(4)52)38(65-41(25)54)46(7,58)48(47,67-45)37(34)64-42(55)30-15-10-8-11-16-30/h8-19,22,25,34-40,58H,20-21,23-24H2,1-7H3/t25-,34+,35+,36-,37+,38-,39+,40-,45-,46-,47-,48-/m0/s1
SMILES	CC(=O)OC[C@]12[C@H](OC(=O)C)[C@H](OC(=O)C)[C@@H]3[C@H]([C@]42O[C@@]3(C)COC(=O)c2cccnc2CC[C@@H](C(=O)O[C@@H]([C@@H]([C@@H]1OC(=O)c1ccccc1)OC(=O)C)[C@]4(C)O)C)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	929.31	Volume:	903.27 ? Van der Waals volume.
Dense:	1.029	LogP:	1.617 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.878 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.692 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	50.0
TPSA:	252.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	1.0	Rings:	7.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.238	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.552	Fsp³:	0.479
MCE-18:	234.394 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.635	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.333 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.013	Promiscuous compounds:	0.072

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.442	MDCK Permeability:	-4.859
Pgp-inhibitor:	0.999	Pgp-substrate:	0.891
PAMPA:	0.963 ? 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):	0.0
20% Bioavailability (F20%):	0.001	30% Bioavailability (F30%):	0.054
50% Bioavailability (F50%):	0.512

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	80.975%	Volume Distribution (VD):	-0.263
Fu:	19.339% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.942	BCRP inhibitor:	0.0
BSEP inhibitor:	0.983

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:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.832 ? 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):

0.959

Half-life (T1/2):

1.354

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.225
Human Hepatotoxicity (H-HT):	0.199	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.888	Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.652	Skin Sensitization:	1.0
Carcinogencity:	0.743	Eye Corrosion:	0.0
Eye Irritation:	0.037	Respiratory Toxicity:	0.048
Drug-induced Neurotoxicity:	0.543	Ototoxicity:	0.398
Hematotoxicity:	0.537	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.983	RPMI-8226 Immunitoxicity:	0.315
A549 Cytotoxicity:	0.529	Hek293 Cytotoxicity:	0.357
BCF:	0.55 ? 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:	3.469 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.855 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.496 ? 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
NPO30152	Maytenus mekongensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21634414]

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
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
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2500.0	nM	PMID[21634414]

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 NPC316841 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	17860
0.1-0.2	30474
0.2-0.3	1144
0.3-0.4	251
0.4-0.5	58
0.5-0.6	25
0.6-0.7	22
0.7-0.8	0
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC328186
0.883	High Similarity	NPC122968
0.883	High Similarity	NPC228377
0.8586	High Similarity	NPC327904
0.837	Intermediate Similarity	NPC250807
0.837	Intermediate Similarity	NPC57797
0.83	Intermediate Similarity	NPC319880
0.83	Intermediate Similarity	NPC320324
0.8218	Intermediate Similarity	NPC38959
0.8081	Intermediate Similarity	NPC475596
0.802	Intermediate Similarity	NPC475406
0.78	Intermediate Similarity	NPC475631
0.7745	Intermediate Similarity	NPC473689
0.7745	Intermediate Similarity	NPC292416
0.7723	Intermediate Similarity	NPC476110
0.7677	Intermediate Similarity	NPC53255
0.7677	Intermediate Similarity	NPC85879
0.767	Intermediate Similarity	NPC244839
0.7525	Intermediate Similarity	NPC475303
0.73	Intermediate Similarity	NPC146824
0.7264	Intermediate Similarity	NPC477787
0.7115	Intermediate Similarity	NPC87152
0.7115	Intermediate Similarity	NPC475600
0.6972	Remote Similarity	NPC327769
0.6733	Remote Similarity	NPC473850
0.6729	Remote Similarity	NPC13603
0.6697	Remote Similarity	NPC475648
0.6667	Remote Similarity	NPC76565
0.6667	Remote Similarity	NPC30456
0.6667	Remote Similarity	NPC488904
0.6667	Remote Similarity	NPC601313
0.6545	Remote Similarity	NPC253482
0.6545	Remote Similarity	NPC600583
0.6545	Remote Similarity	NPC601643
0.6542	Remote Similarity	NPC475301
0.6496	Remote Similarity	NPC482915
0.6372	Remote Similarity	NPC471979
0.6364	Remote Similarity	NPC475644
0.6271	Remote Similarity	NPC483854
0.625	Remote Similarity	NPC237702
0.6204	Remote Similarity	NPC475362
0.619	Remote Similarity	NPC471016
0.6147	Remote Similarity	NPC326930
0.6091	Remote Similarity	NPC607403
0.6018	Remote Similarity	NPC483893
0.5893	Remote Similarity	NPC470486
0.5893	Remote Similarity	NPC477788
0.5877	Remote Similarity	NPC483894
0.5862	Remote Similarity	NPC328928
0.5752	Remote Similarity	NPC328154
0.5752	Remote Similarity	NPC471977
0.5714	Remote Similarity	NPC475426
0.5678	Remote Similarity	NPC483853
0.5678	Remote Similarity	NPC608314
0.5603	Remote Similarity	NPC600607
0.5603	Remote Similarity	NPC611166
0.5556	Remote Similarity	NPC470306
0.5505	Remote Similarity	NPC35208
0.5495	Remote Similarity	NPC475498
0.5431	Remote Similarity	NPC471190
0.536	Remote Similarity	NPC483856
0.5315	Remote Similarity	NPC475137
0.5276	Remote Similarity	NPC483855
0.5259	Remote Similarity	NPC475533
0.5175	Remote Similarity	NPC483892
0.5169	Remote Similarity	NPC324619
0.51	Remote Similarity	NPC472570
0.5042	Remote Similarity	NPC483895
0.5042	Remote Similarity	NPC600224
0.5041	Remote Similarity	NPC600546

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC316841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3739
0.1-0.2	5351
0.2-0.3	58
0.3-0.4	2
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