NPASS Compound

Natural Product: NPC477014

Natural Product ID	NPC477014
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Plagioneurin B
IUPAC Name	[(1S)-1,8-dihydroxy-1-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]-15-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]pentadecan-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44583896
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 117118 0 0 0 0 0 0 0 0999 V2000 10.6275 -1.8753 2.3602 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7591 -0.3829 2.5805 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8853 0.1062 1.6792 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4265 -0.2471 0.2477 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4323 0.1757 -0.7551 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1984 -0.2022 -2.1307 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0940 0.1046 -3.0037 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7219 -0.3249 -2.9036 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7655 -0.0546 -1.8582 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4424 1.3902 -1.5826 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4497 1.4308 -0.4485 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1640 0.7333 -0.6874 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4113 1.3335 -1.8841 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1315 0.5427 -1.9983 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3749 -0.8629 -2.4004 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3276 -1.6373 -1.6140 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9090 -0.6781 -0.5601 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5656 0.5241 -0.7245 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3949 -0.4510 -0.4948 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1527 0.2455 0.8197 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2638 0.5935 1.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2280 -0.5410 1.1488 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6024 0.0560 1.4436 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6903 -0.9678 1.5122 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0058 -0.2566 1.7997 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1300 -1.2914 1.8634 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3932 -0.5422 2.1435 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6269 -1.3583 2.2492 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0088 -2.1267 1.0202 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2517 -1.2360 -0.1793 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3772 -0.2783 0.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5654 0.5890 -1.0771 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6545 1.5825 -0.8351 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9410 0.9121 -0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6270 1.0595 0.5927 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8434 0.2458 0.5377 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.8112 -0.3842 -0.7111 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.6668 -0.0054 -1.3919 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3127 -0.3861 -2.5536 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.8395 -0.8338 1.6066 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2182 -1.9197 0.6315 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7395 1.5466 0.1621 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1171 2.8045 0.6122 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0469 3.1204 1.8434 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6136 3.7953 -0.3807 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 -1.7436 -0.3500 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1469 2.6534 -1.4908 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7321 -2.1175 1.7309 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5485 -2.2915 1.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4987 -2.3382 3.3566 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9982 -0.1260 3.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8103 0.1365 2.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9158 1.2075 1.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8127 -0.4093 1.9170 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0186 -1.2479 0.1686 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5506 0.4773 0.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6974 1.2752 -0.6253 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4248 -0.3050 -0.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1574 0.1433 -2.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4256 -1.3630 -2.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1755 1.2344 -3.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4359 -0.2864 -4.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1974 -0.0773 -3.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7384 -1.4827 -3.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7523 -0.4530 -2.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8173 -0.5941 -0.9021 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3131 1.9971 -1.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9673 1.8070 -2.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1937 2.5266 -0.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9237 1.1503 0.5231 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4986 0.9850 0.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2075 -0.3494 -0.7155 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0406 1.2692 -2.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4347 1.0641 -2.7124 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1139 -0.9657 -3.4948 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3829 -1.2519 -2.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8238 -2.5121 -1.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4947 -1.9327 -2.2582 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1829 -1.0477 0.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0208 0.0954 -1.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6017 -0.4185 1.5994 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8008 1.1598 0.7976 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2723 1.0531 2.1363 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9990 -1.2426 1.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3041 -1.0204 0.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8725 0.7984 0.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5818 0.6134 2.4011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8329 -1.5032 0.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4768 -1.6696 2.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2079 0.5100 1.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9915 0.2285 2.7930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8976 -2.0043 2.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3089 0.0614 3.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4717 0.2394 1.3291 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5242 -0.7583 2.5478 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4609 -2.1407 3.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9604 -2.6637 1.2752 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2890 -2.9028 0.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5981 -1.8791 -1.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3667 -0.6578 -0.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2796 -0.8695 0.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0717 0.4106 0.9728 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7856 -0.0943 -1.9386 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6114 1.0822 -1.2685 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7645 2.2272 -1.7360 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3434 2.2334 -0.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3251 1.6880 1.4189 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7528 0.8672 0.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8814 -1.0420 1.8815 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3014 -0.4367 2.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3870 -1.7777 1.2127 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7983 -1.3455 -0.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6285 4.7971 0.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6252 3.4796 -0.6606 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9324 3.7434 -1.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2949 -2.1017 0.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2465 2.9473 -1.7846 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 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 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 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 36 40 1 0 26 41 1 0 21 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 19 46 1 0 13 47 1 0 18 14 1 0 38 34 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 2 52 1 0 3 53 1 0 3 54 1 0 4 55 1 0 4 56 1 0 5 57 1 0 5 58 1 0 6 59 1 0 6 60 1 0 7 61 1 0 7 62 1 0 8 63 1 0 8 64 1 0 9 65 1 0 9 66 1 0 10 67 1 0 10 68 1 0 11 69 1 0 11 70 1 0 12 71 1 0 12 72 1 0 13 73 1 6 14 74 1 6 15 75 1 0 15 76 1 0 16 77 1 0 16 78 1 0 17 79 1 1 19 80 1 6 20 81 1 0 20 82 1 0 21 83 1 0 22 84 1 0 22 85 1 0 23 86 1 0 23 87 1 0 24 88 1 0 24 89 1 0 25 90 1 0 25 91 1 0 26 92 1 0 27 93 1 0 27 94 1 0 28 95 1 0 28 96 1 0 29 97 1 0 29 98 1 0 30 99 1 0 30100 1 0 31101 1 0 31102 1 0 32103 1 0 32104 1 0 33105 1 0 33106 1 0 35107 1 0 36108 1 6 40109 1 0 40110 1 0 40111 1 0 41112 1 0 45113 1 0 45114 1 0 45115 1 0 46116 1 0 47117 1 0 M END

Standard InCHIKey	VIGZEOWQMKUZQP-NKWRIIGESA-N
Standard InCHI	InChI=1S/C39H70O8/c1-4-5-6-7-8-9-10-11-15-18-25-35(42)37-26-27-38(47-37)36(43)29-34(46-31(3)40)24-20-19-23-33(41)22-17-14-12-13-16-21-32-28-30(2)45-39(32)44/h28,30,33-38,41-43H,4-27,29H2,1-3H3/t30-,33?,34?,35-,36-,37+,38+/m0/s1
SMILES	CCCCCCCCCCCC[C@@H]([C@H]1CC[C@@H](O1)[C@H](CC(CCCCC(CCCCCCCC2=C[C@@H](OC2=O)C)O)OC(=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.51	Volume:	728.399 ? Van der Waals volume.
Dense:	0.915	LogP:	6.115 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.975 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.14 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	30.0	Rigid Bonds:	12.0
TPSA:	122.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.054	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.764	Fsp³:	0.897
MCE-18:	34.162 ? 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:	0.84	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.057 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.444	Promiscuous compounds:	0.204

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.286	MDCK Permeability:	-4.83
Pgp-inhibitor:	0.226	Pgp-substrate:	0.903
PAMPA:	0.002 ? 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):	0.962
20% Bioavailability (F20%):	0.993	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	97.456%	Volume Distribution (VD):	0.439
Fu:	2.305% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.776
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.955
BSEP inhibitor:	0.948

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.048	CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.972
CYP3A4-inhibitor:	0.007	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.685 ? 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):

5.161

Half-life (T1/2):

1.404

ADMET: Toxicity

hERG Blockers:	0.532	hERG Blockers (10um):	0.862
Human Hepatotoxicity (H-HT):	0.708	Drug-induced Liver Injury (DILI):	0.25
AMES Toxicity:	0.136	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.907	Skin Sensitization:	1.0
Carcinogencity:	0.271	Eye Corrosion:	0.004
Eye Irritation:	0.57	Respiratory Toxicity:	0.875
Drug-induced Neurotoxicity:	0.041	Ototoxicity:	0.887
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.978
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.092
A549 Cytotoxicity:	0.819	Hek293 Cytotoxicity:	0.121
BCF:	0.716 ? 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:	5.176 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.704 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.936 ? 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
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	leaves	Tam Kim, Cao Bang Province, in North Vietnam	2000-JUN	PMID[16989521]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	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	1

Activity Type	# Activity
Cell line	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
NPT91	Cell line	KB	Homo sapiens	IC50	=	6.5	nM	PMID[16989521]

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 NPC477014 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	17819
0.1-0.2	28961
0.2-0.3	2746
0.3-0.4	94
0.4-0.5	36
0.5-0.6	63
0.6-0.7	90
0.7-0.8	0
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477013
0.8364	Intermediate Similarity	NPC477015
0.8246	Intermediate Similarity	NPC477017
0.8246	Intermediate Similarity	NPC477016
0.8163	Intermediate Similarity	NPC475159
0.8163	Intermediate Similarity	NPC131002
0.8163	Intermediate Similarity	NPC473780
0.8163	Intermediate Similarity	NPC604521
0.7963	Intermediate Similarity	NPC258068
0.7963	Intermediate Similarity	NPC476583
0.7843	Intermediate Similarity	NPC156804
0.7692	Intermediate Similarity	NPC163093
0.7551	Intermediate Similarity	NPC73310
0.7551	Intermediate Similarity	NPC473529
0.7551	Intermediate Similarity	NPC180363
0.7551	Intermediate Similarity	NPC94875
0.7551	Intermediate Similarity	NPC11332
0.7551	Intermediate Similarity	NPC145914
0.7551	Intermediate Similarity	NPC601174
0.7551	Intermediate Similarity	NPC601403
0.7551	Intermediate Similarity	NPC603568
0.7551	Intermediate Similarity	NPC604330
0.7551	Intermediate Similarity	NPC608300
0.7551	Intermediate Similarity	NPC611200
0.7551	Intermediate Similarity	NPC611571
0.7547	Intermediate Similarity	NPC241360
0.7547	Intermediate Similarity	NPC293136
0.7451	Intermediate Similarity	NPC100921
0.7451	Intermediate Similarity	NPC477018
0.7358	Intermediate Similarity	NPC473156
0.7358	Intermediate Similarity	NPC282815
0.7358	Intermediate Similarity	NPC600956
0.7273	Intermediate Similarity	NPC329838
0.7222	Intermediate Similarity	NPC473671
0.7222	Intermediate Similarity	NPC475268
0.7222	Intermediate Similarity	NPC470400
0.7222	Intermediate Similarity	NPC77871
0.7222	Intermediate Similarity	NPC9678
0.7222	Intermediate Similarity	NPC319036
0.7222	Intermediate Similarity	NPC605867
0.7115	Intermediate Similarity	NPC329829
0.7091	Intermediate Similarity	NPC65930
0.7091	Intermediate Similarity	NPC132940
0.7037	Intermediate Similarity	NPC610454
0.7018	Intermediate Similarity	NPC120398
0.7018	Intermediate Similarity	NPC471567
0.6964	Remote Similarity	NPC20533
0.6792	Remote Similarity	NPC107986
0.6792	Remote Similarity	NPC25764
0.6792	Remote Similarity	NPC235809
0.6792	Remote Similarity	NPC223871
0.6792	Remote Similarity	NPC231009
0.6792	Remote Similarity	NPC103284
0.6792	Remote Similarity	NPC110710
0.6792	Remote Similarity	NPC39279
0.6792	Remote Similarity	NPC1083
0.6792	Remote Similarity	NPC39167
0.6792	Remote Similarity	NPC82795
0.6792	Remote Similarity	NPC292809
0.6792	Remote Similarity	NPC286338
0.6792	Remote Similarity	NPC202055
0.6792	Remote Similarity	NPC603931
0.6792	Remote Similarity	NPC604237
0.6792	Remote Similarity	NPC606804
0.6792	Remote Similarity	NPC607425
0.6792	Remote Similarity	NPC608574
0.6727	Remote Similarity	NPC473649
0.6727	Remote Similarity	NPC154097
0.6727	Remote Similarity	NPC144415
0.6727	Remote Similarity	NPC159750
0.6727	Remote Similarity	NPC73248
0.6727	Remote Similarity	NPC470401
0.6727	Remote Similarity	NPC607439
0.6727	Remote Similarity	NPC608157
0.6724	Remote Similarity	NPC473995
0.6667	Remote Similarity	NPC309211
0.6667	Remote Similarity	NPC329615
0.6667	Remote Similarity	NPC20621
0.6667	Remote Similarity	NPC488253
0.6667	Remote Similarity	NPC473669
0.6667	Remote Similarity	NPC318963
0.6667	Remote Similarity	NPC280612
0.6667	Remote Similarity	NPC488251
0.6667	Remote Similarity	NPC477010
0.6667	Remote Similarity	NPC605101
0.661	Remote Similarity	NPC89001
0.6607	Remote Similarity	NPC604764
0.6604	Remote Similarity	NPC606043
0.6545	Remote Similarity	NPC232555
0.6545	Remote Similarity	NPC171174
0.6545	Remote Similarity	NPC182383
0.6545	Remote Similarity	NPC114694
0.6545	Remote Similarity	NPC485248
0.6545	Remote Similarity	NPC142117
0.6545	Remote Similarity	NPC480249
0.6545	Remote Similarity	NPC485249
0.6545	Remote Similarity	NPC240695
0.6491	Remote Similarity	NPC178215
0.6429	Remote Similarity	NPC488632
0.6429	Remote Similarity	NPC477011
0.6393	Remote Similarity	NPC473520
0.6333	Remote Similarity	NPC320458
0.6333	Remote Similarity	NPC480082
0.6316	Remote Similarity	NPC219652
0.6316	Remote Similarity	NPC473840
0.629	Remote Similarity	NPC253801
0.6271	Remote Similarity	NPC473478
0.6271	Remote Similarity	NPC473651
0.6271	Remote Similarity	NPC139418
0.6271	Remote Similarity	NPC66346
0.6167	Remote Similarity	NPC283085
0.6167	Remote Similarity	NPC169511
0.6167	Remote Similarity	NPC287164
0.6167	Remote Similarity	NPC234077
0.614	Remote Similarity	NPC93794
0.614	Remote Similarity	NPC134865
0.614	Remote Similarity	NPC473504
0.614	Remote Similarity	NPC103523
0.614	Remote Similarity	NPC81778
0.614	Remote Similarity	NPC40066
0.614	Remote Similarity	NPC488627
0.614	Remote Similarity	NPC47937
0.614	Remote Similarity	NPC488631
0.6129	Remote Similarity	NPC488630
0.6129	Remote Similarity	NPC488625
0.6129	Remote Similarity	NPC488626
0.6102	Remote Similarity	NPC485250
0.6102	Remote Similarity	NPC488250
0.6102	Remote Similarity	NPC605396
0.6034	Remote Similarity	NPC280621
0.6034	Remote Similarity	NPC25703
0.6034	Remote Similarity	NPC48338
0.6034	Remote Similarity	NPC488628
0.6	Remote Similarity	NPC69082
0.6	Remote Similarity	NPC482766
0.6	Remote Similarity	NPC488249
0.5965	Remote Similarity	NPC81045
0.5965	Remote Similarity	NPC39754
0.5965	Remote Similarity	NPC171135
0.5965	Remote Similarity	NPC61257
0.5965	Remote Similarity	NPC320569
0.5965	Remote Similarity	NPC133730
0.5965	Remote Similarity	NPC191929
0.5965	Remote Similarity	NPC100454
0.5965	Remote Similarity	NPC242364
0.5965	Remote Similarity	NPC172821
0.5965	Remote Similarity	NPC274446
0.5965	Remote Similarity	NPC485251
0.5965	Remote Similarity	NPC151403
0.5965	Remote Similarity	NPC261952
0.5965	Remote Similarity	NPC605171
0.5932	Remote Similarity	NPC42598
0.5932	Remote Similarity	NPC473687
0.5932	Remote Similarity	NPC204686
0.5932	Remote Similarity	NPC219498
0.5932	Remote Similarity	NPC308412
0.5932	Remote Similarity	NPC134885
0.5932	Remote Similarity	NPC488247
0.5932	Remote Similarity	NPC210218
0.5932	Remote Similarity	NPC488248
0.5902	Remote Similarity	NPC231096
0.5902	Remote Similarity	NPC475581
0.5902	Remote Similarity	NPC62118
0.5902	Remote Similarity	NPC132496
0.5902	Remote Similarity	NPC107717
0.5902	Remote Similarity	NPC488252
0.5873	Remote Similarity	NPC322529
0.5873	Remote Similarity	NPC91067
0.5862	Remote Similarity	NPC600524
0.5862	Remote Similarity	NPC608355
0.5833	Remote Similarity	NPC602738
0.5806	Remote Similarity	NPC488623
0.5806	Remote Similarity	NPC488624
0.5806	Remote Similarity	NPC233551
0.5806	Remote Similarity	NPC40376
0.5806	Remote Similarity	NPC21208
0.5806	Remote Similarity	NPC488629
0.5781	Remote Similarity	NPC473905
0.5769	Remote Similarity	NPC609415
0.5738	Remote Similarity	NPC477012
0.5692	Remote Similarity	NPC473663
0.5692	Remote Similarity	NPC473723
0.5692	Remote Similarity	NPC475173
0.5645	Remote Similarity	NPC130359
0.5645	Remote Similarity	NPC14901
0.5625	Remote Similarity	NPC480081
0.5574	Remote Similarity	NPC134807
0.5484	Remote Similarity	NPC20339
0.5472	Remote Similarity	NPC608138
0.5469	Remote Similarity	NPC239517
0.5424	Remote Similarity	NPC488234
0.5397	Remote Similarity	NPC606740
0.5397	Remote Similarity	NPC608614
0.5333	Remote Similarity	NPC482767
0.5333	Remote Similarity	NPC475260
0.5333	Remote Similarity	NPC488621
0.5333	Remote Similarity	NPC473775
0.5333	Remote Similarity	NPC488622
0.5294	Remote Similarity	NPC279267

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6707
0.1-0.2	2399
0.2-0.3	44
0.3-0.4	0
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