NPASS Compound

Natural Product: NPC88369

Natural Product ID	NPC88369
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KRQDMAXNTWLTDZ-FXQMNGNYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	73606
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal 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 114121 0 0 0 0 0 0 0 0999 V2000 -11.7994 0.5659 -0.2880 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1210 -0.7212 0.1900 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2077 -0.3625 1.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9488 0.2526 0.7292 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2244 -0.7973 -0.0505 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1598 -0.2124 -0.9638 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6912 0.7128 -1.9907 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2699 0.4380 0.0795 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3704 -0.6150 1.1940 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9798 -1.2775 1.1762 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1509 -0.0820 0.9112 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7013 -0.3068 0.5981 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0518 -0.9912 1.7545 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7461 -0.4585 2.1597 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0581 0.4394 1.4691 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2372 0.9151 1.9525 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1342 1.2735 0.8069 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4677 2.1968 -0.1486 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0114 2.3186 -0.0377 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6455 0.9572 0.2132 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3324 0.0584 -0.9445 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1156 1.0927 0.4653 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7929 1.8924 -0.5984 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2894 1.8893 -0.4997 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8299 0.5123 -0.3100 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5420 -0.2780 -1.5652 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4400 0.0762 0.1252 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8178 -0.1664 0.1255 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1474 -1.5196 0.7273 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5664 -1.9321 0.3897 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3460 -0.8359 -0.2976 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5235 -0.2062 -1.4147 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9369 1.2313 -1.6661 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6320 2.0781 -0.6077 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1737 -0.2550 -1.2194 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4401 -1.4385 -0.9360 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6656 -0.9051 -0.5401 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6275 -1.9741 -0.0938 C 0 0 1 0 0 0 0 0 0 0 0 0 11.0130 -1.3863 -0.0823 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0548 0.1050 -0.1972 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1964 0.6243 -1.3251 C 0 0 1 0 0 0 0 0 0 0 0 0 11.0045 1.0319 -2.5321 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2140 -0.3014 -1.6790 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7159 0.7483 0.9877 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8597 -2.0195 -0.9905 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2906 -2.5197 1.1476 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2576 -2.3216 1.5328 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8825 -1.5893 2.0878 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3815 -1.4746 0.8648 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0578 -1.7675 -0.6716 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.3987 -1.3595 -0.9496 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9017 0.4876 -0.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5215 1.4335 0.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4856 0.7708 -1.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9284 -1.3623 0.6118 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7237 0.4032 1.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9355 -1.2425 1.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1951 1.1539 0.1317 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3446 0.6073 1.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6784 -1.1010 -1.4383 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7714 0.9407 -1.8924 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5853 0.2720 -3.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0841 1.6493 -2.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7115 1.3861 0.3783 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4670 -0.1510 2.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9146 -2.0772 0.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7789 -1.7355 2.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2138 0.6261 1.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 -0.9301 -0.2920 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9036 -2.0849 1.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7196 -0.9787 2.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3149 -0.8152 3.0746 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7269 0.1824 2.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0966 1.8860 2.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1131 1.6999 1.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7814 1.9657 -1.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8936 3.2302 0.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3425 3.0711 0.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4078 2.6609 -1.0336 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0115 -0.9313 -0.6145 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2376 -0.1334 -1.5799 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4398 0.4969 -1.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2544 1.6215 1.4319 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4130 1.6507 -1.6249 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4727 2.9663 -0.4462 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6804 2.3393 -1.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6028 2.5366 0.3446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2961 0.0836 -2.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5633 -1.3604 -1.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5755 0.0155 -1.9745 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3767 0.6040 0.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4679 -2.2455 0.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5711 -2.7980 -0.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6503 -0.0554 0.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7173 -0.7522 -2.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0196 1.3103 -1.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3959 1.6511 -2.5507 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4632 2.3999 -0.1374 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4845 -0.1364 0.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6365 -2.8046 -0.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4542 -1.6276 0.9300 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1023 0.3860 -0.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6700 1.5228 -0.9557 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6720 2.0264 -2.8897 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0043 0.2718 -3.3404 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0742 1.1538 -2.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8847 0.0677 1.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2959 -2.2511 -1.7957 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1125 -3.0348 1.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7955 -1.5582 1.8393 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4295 -0.9681 2.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0878 -2.6893 -0.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9712 -2.2997 -1.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4848 -0.7412 -1.8848 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 6 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 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 32 35 1 0 31 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 40 44 1 0 39 45 1 0 38 46 1 0 30 47 1 0 29 48 1 0 9 49 1 0 5 50 1 0 50 51 1 0 51 2 1 0 49 5 1 0 25 8 1 0 35 28 1 0 43 37 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 1 3 56 1 0 3 57 1 0 4 58 1 0 4 59 1 0 6 60 1 6 7 61 1 0 7 62 1 0 7 63 1 0 8 64 1 1 9 65 1 1 10 66 1 0 10 67 1 0 11 68 1 1 12 69 1 6 13 70 1 0 13 71 1 0 14 72 1 0 16 73 1 0 16 74 1 0 17 75 1 1 18 76 1 0 18 77 1 0 19 78 1 0 19 79 1 0 21 80 1 0 21 81 1 0 21 82 1 0 22 83 1 1 23 84 1 0 23 85 1 0 24 86 1 0 24 87 1 0 26 88 1 0 26 89 1 0 26 90 1 0 28 91 1 1 29 92 1 6 30 93 1 6 31 94 1 1 32 95 1 6 33 96 1 0 33 97 1 0 34 98 1 0 37 99 1 1 38100 1 6 39101 1 1 40102 1 6 41103 1 1 42104 1 0 42105 1 0 42106 1 0 44107 1 0 45108 1 0 46109 1 0 47110 1 0 48111 1 0 50112 1 0 51113 1 0 51114 1 0 M END

Standard InCHIKey	KRQDMAXNTWLTDZ-FXQMNGNYSA-N
Standard InCHI	InChI=1S/C39H63NO11/c1-18-8-13-39(40-16-18)19(2)28-26(51-39)15-25-23-7-6-21-14-22(9-11-37(21,4)24(23)10-12-38(25,28)5)48-36-33(46)31(44)34(27(17-41)49-36)50-35-32(45)30(43)29(42)20(3)47-35/h6,18-20,22-36,40-46H,7-17H2,1-5H3/t18-,19+,20-,22+,23-,24+,25+,26+,27+,28+,29-,30+,31+,32-,33-,34+,35+,36-,37+,38+,39?/m1/s1
SMILES	C[C@@H]1CCC2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](CO)O3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O)O)O)O)O)O2)NC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	721.44	Volume:	719.701 ? Van der Waals volume.
Dense:	1.002	LogP:	3.811 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.159 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.081 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	179.56 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	8.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.206	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.299	Fsp³:	0.949
MCE-18:	198.421 ? 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:	0.86	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:	0.007	Promiscuous compounds:	0.019

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.385	MDCK Permeability:	-5.112
Pgp-inhibitor:	0.0	Pgp-substrate:	0.448
PAMPA:	0.962 ? 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%):	0.003	30% Bioavailability (F30%):	0.114
50% Bioavailability (F50%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307	MRP1:	0.37
Plasma Protein Binding (PPB):	65.123%	Volume Distribution (VD):	-0.306
Fu:	31.753% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.268
BSEP inhibitor:	0.758

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.983	CYP3A4-substrate:	0.93
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.605
HLM stability:	0.627 ? 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):

2.123

Half-life (T1/2):

2.248

ADMET: Toxicity

hERG Blockers:	0.115	hERG Blockers (10um):	0.289
Human Hepatotoxicity (H-HT):	0.368	Drug-induced Liver Injury (DILI):	0.805
AMES Toxicity:	0.835	Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.132	Skin Sensitization:	0.998
Carcinogencity:	0.161	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.054
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.984
Hematotoxicity:	0.158	Drug-induced Nephrotoxicity:	0.537
Genotoxicity:	0.022	RPMI-8226 Immunitoxicity:	0.203
A549 Cytotoxicity:	0.788	Hek293 Cytotoxicity:	0.741
BCF:	1.708 ? 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:	3.496 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.758 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.108 ? 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
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	Whole plant	n.a.	steroidal saponins	PMID[16933867]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2211	Solanum nigrum	Species	Solanaceae	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

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

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 NPC88369 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	23480
0.1-0.2	23080
0.2-0.3	2688
0.3-0.4	472
0.4-0.5	70
0.5-0.6	50
0.6-0.7	9
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC15249
1.0	High Similarity	NPC25455
0.8478	Intermediate Similarity	NPC122819
0.7917	Intermediate Similarity	NPC150057
0.7917	Intermediate Similarity	NPC147753
0.7573	Intermediate Similarity	NPC287885
0.6735	Remote Similarity	NPC470432
0.6735	Remote Similarity	NPC230507
0.6452	Remote Similarity	NPC486114
0.6442	Remote Similarity	NPC6806
0.6364	Remote Similarity	NPC485606
0.6136	Remote Similarity	NPC147835
0.6136	Remote Similarity	NPC253645
0.6136	Remote Similarity	NPC85001
0.6136	Remote Similarity	NPC95920
0.5769	Remote Similarity	NPC94272
0.5648	Remote Similarity	NPC470433
0.5648	Remote Similarity	NPC46190
0.5648	Remote Similarity	NPC171073
0.5625	Remote Similarity	NPC247037
0.5625	Remote Similarity	NPC269297
0.5625	Remote Similarity	NPC222202
0.5596	Remote Similarity	NPC248746
0.5596	Remote Similarity	NPC477809
0.5586	Remote Similarity	NPC73243
0.5586	Remote Similarity	NPC244086
0.5586	Remote Similarity	NPC84956
0.5565	Remote Similarity	NPC23808
0.5565	Remote Similarity	NPC87998
0.5545	Remote Similarity	NPC42171
0.5514	Remote Similarity	NPC14704
0.5495	Remote Similarity	NPC480555
0.5495	Remote Similarity	NPC150372
0.5455	Remote Similarity	NPC296686
0.5364	Remote Similarity	NPC602423
0.5351	Remote Similarity	NPC475550
0.5347	Remote Similarity	NPC181845
0.5345	Remote Similarity	NPC249265
0.5345	Remote Similarity	NPC480554
0.531	Remote Similarity	NPC102016
0.531	Remote Similarity	NPC95051
0.5304	Remote Similarity	NPC475333
0.5304	Remote Similarity	NPC224098
0.5304	Remote Similarity	NPC208383
0.5273	Remote Similarity	NPC98696
0.5268	Remote Similarity	NPC300557
0.5259	Remote Similarity	NPC194207
0.5259	Remote Similarity	NPC22779
0.5254	Remote Similarity	NPC480553
0.5254	Remote Similarity	NPC477811
0.5248	Remote Similarity	NPC165439
0.5246	Remote Similarity	NPC224314
0.5234	Remote Similarity	NPC295980
0.5229	Remote Similarity	NPC305423
0.5229	Remote Similarity	NPC113044
0.5229	Remote Similarity	NPC283829
0.5229	Remote Similarity	NPC161676
0.5221	Remote Similarity	NPC475182
0.521	Remote Similarity	NPC308140
0.5089	Remote Similarity	NPC265275
0.5085	Remote Similarity	NPC218571
0.5085	Remote Similarity	NPC487615
0.5043	Remote Similarity	NPC309278
0.5041	Remote Similarity	NPC232054
0.5041	Remote Similarity	NPC480556

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC88369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7436
0.1-0.2	1626
0.2-0.3	78
0.3-0.4	6
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD8449	Approved
0.7917	Intermediate Similarity	NPD8450	Suspended

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