NPASS Compound

Natural Product: NPC277431

Natural Product ID	NPC277431
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NCIZYLQHZNMNLA-FOAHKCLGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	72722317
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 10.5285 3.3447 0.4413 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3442 1.8618 0.7509 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2333 1.1283 -0.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8526 1.2263 -1.1217 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8497 0.8211 -0.0958 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0874 -0.4461 -0.5010 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8057 -1.6804 0.0008 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8370 -0.2835 0.3172 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8645 1.1519 0.7943 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4574 1.7096 0.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6660 0.4645 0.4443 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2717 0.5750 -0.0432 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5092 1.4264 0.9666 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0560 1.3207 0.7914 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4692 0.2480 0.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9464 0.1695 0.1079 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5456 -1.0780 0.6446 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6596 -2.2375 0.8691 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -2.1066 0.6343 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2680 -0.9632 -0.1916 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1631 -1.2007 -1.6342 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7402 -0.8676 -0.0433 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5420 -1.6398 -1.0489 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9755 -1.7407 -0.5419 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5718 -0.3653 -0.4620 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6563 0.2387 -1.8289 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5084 -1.4886 -0.3156 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7943 -1.4427 0.1566 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6179 -0.6201 -0.8172 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3195 -1.5400 -1.8247 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3230 -2.4132 -1.0820 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7135 -2.7376 0.2692 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0932 -4.1376 0.7303 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6528 -5.0220 -0.2642 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3326 -2.7310 0.1354 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5368 -1.7304 -0.9365 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3264 -2.3931 -2.3293 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6028 0.0811 -0.1592 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5128 1.4482 -0.4459 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7818 1.8457 -1.1689 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9750 1.8658 -0.2367 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6316 2.3635 1.1355 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3293 1.8036 1.6572 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0319 2.4796 2.9759 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3341 2.1327 0.7350 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6377 1.9973 2.0074 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9069 2.7461 -0.8065 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5587 3.0639 -1.7863 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8143 1.7774 0.0291 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3866 0.5794 1.2099 N 0 0 0 0 0 0 0 0 0 0 0 0 9.1401 1.7380 1.6339 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5287 3.7282 0.1680 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8460 3.8471 1.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2538 3.4655 -0.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2558 1.5076 1.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5945 0.0826 -0.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9317 1.6344 -1.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8036 0.4942 -1.9764 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6858 2.2420 -1.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9315 -0.5063 -1.5761 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8918 -1.6357 -0.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3214 -2.5582 -0.4732 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5843 -1.7728 1.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7667 -1.0048 1.1604 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1644 1.2466 1.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4153 2.3748 -0.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1670 2.2323 1.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6540 -0.0518 1.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1315 1.0515 -1.0153 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7903 1.0401 1.9737 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8979 2.4422 0.8743 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5724 2.1484 1.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1248 0.2897 -0.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4541 1.0551 0.5577 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1620 -0.8231 1.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7743 -2.5042 1.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0593 -3.1900 0.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3931 -2.1277 1.5875 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1514 -3.0391 0.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1375 -1.7111 -1.6766 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5543 -1.8297 -2.1875 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3158 -0.1961 -2.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0445 -1.2656 0.9710 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1325 -2.6691 -1.0959 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4985 -1.2243 -2.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9595 -2.2524 0.4252 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5454 -2.3332 -1.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6599 0.4496 -2.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2529 1.1605 -1.8662 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1278 -0.4853 -2.5236 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8765 -1.0939 1.1998 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9845 0.0647 -1.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7708 -0.9011 -2.5816 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4913 -3.3250 -1.6598 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9931 -1.9745 1.0210 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4477 -4.3525 1.6196 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1647 -4.2443 0.9514 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7689 -5.4142 -0.0569 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0756 -2.2709 -0.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5188 -3.3439 -2.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6765 1.6861 -1.1328 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9865 1.0626 -1.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4730 0.8622 -0.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5552 3.4752 1.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4355 0.7040 1.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5716 3.4446 3.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9504 2.6995 3.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3447 1.8631 3.8546 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4593 1.8212 1.5172 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3138 2.3566 -1.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3300 2.8918 -2.7484 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0070 -0.2347 1.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4779 2.6280 1.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4281 1.5406 2.7043 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 30 37 1 0 29 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 1 0 43 45 1 0 42 46 1 0 41 47 1 0 40 48 1 0 9 49 1 0 5 50 1 0 50 51 1 0 51 2 1 0 5 49 1 1 25 8 1 0 35 28 1 0 45 39 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 6 32 95 1 1 33 96 1 0 33 97 1 0 34 98 1 0 36 99 1 0 37100 1 0 39101 1 6 40102 1 6 41103 1 1 42104 1 6 43105 1 1 44106 1 0 44107 1 0 44108 1 0 46109 1 0 47110 1 0 48111 1 0 50112 1 0 51113 1 0 51114 1 0 M END

Standard InCHIKey	NCIZYLQHZNMNLA-FOAHKCLGSA-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)48-36-34(32(45)30(43)27(17-41)49-36)50-35-33(46)31(44)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]1CC[C@@]2([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)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)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:	3.031 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.696 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.847 ? 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:	6.295	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:	0.872	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.02

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.944	MDCK Permeability:	-5.137
Pgp-inhibitor:	0.0	Pgp-substrate:	0.673
PAMPA:	0.971 ? 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%):	0.021	30% Bioavailability (F30%):	0.691
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038	MRP1:	0.048
Plasma Protein Binding (PPB):	66.707%	Volume Distribution (VD):	-0.371
Fu:	28.236% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.467
BSEP inhibitor:	0.083

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.046	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.123	CYP3A4-substrate:	0.99
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.181
HLM stability:	0.391 ? 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):

1.642

Half-life (T1/2):

2.392

ADMET: Toxicity

hERG Blockers:	0.089	hERG Blockers (10um):	0.218
Human Hepatotoxicity (H-HT):	0.486	Drug-induced Liver Injury (DILI):	0.812
AMES Toxicity:	0.789	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.066	Skin Sensitization:	0.999
Carcinogencity:	0.137	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.986
Hematotoxicity:	0.167	Drug-induced Nephrotoxicity:	0.546
Genotoxicity:	0.036	RPMI-8226 Immunitoxicity:	0.208
A549 Cytotoxicity:	0.737	Hek293 Cytotoxicity:	0.729
BCF:	2.015 ? 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:	3.59 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.768 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.231 ? 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
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21524113]
NPO7703	Xanthorrhoea preissii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8173	Lupinus multiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6023	Neurolaena venturana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6023	Neurolaena venturana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7703	Xanthorrhoea preissii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2383	Mimosa acacioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5425	Polygala nyikensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10340	Crepis rubra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8173	Lupinus multiflorus	Species	Fabaceae	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 NPC277431 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	24304
0.1-0.2	22065
0.2-0.3	2657
0.3-0.4	675
0.4-0.5	80
0.5-0.6	59
0.6-0.7	8
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8404	Intermediate Similarity	NPC122819
0.8229	Intermediate Similarity	NPC150057
0.8229	Intermediate Similarity	NPC147753
0.7957	Intermediate Similarity	NPC15249
0.7957	Intermediate Similarity	NPC25455
0.7524	Intermediate Similarity	NPC287885
0.6765	Remote Similarity	NPC98696
0.6733	Remote Similarity	NPC305423
0.6733	Remote Similarity	NPC113044
0.6733	Remote Similarity	NPC283829
0.6733	Remote Similarity	NPC161676
0.6154	Remote Similarity	NPC485606
0.6058	Remote Similarity	NPC94272
0.6019	Remote Similarity	NPC600456
0.5943	Remote Similarity	NPC470748
0.5943	Remote Similarity	NPC600116
0.5934	Remote Similarity	NPC147835
0.5934	Remote Similarity	NPC253645
0.5934	Remote Similarity	NPC85001
0.5934	Remote Similarity	NPC95920
0.5872	Remote Similarity	NPC477809
0.5856	Remote Similarity	NPC73243
0.5856	Remote Similarity	NPC244086
0.5856	Remote Similarity	NPC84956
0.5766	Remote Similarity	NPC480555
0.5766	Remote Similarity	NPC150372
0.5752	Remote Similarity	NPC247037
0.5714	Remote Similarity	NPC102016
0.5714	Remote Similarity	NPC95051
0.5688	Remote Similarity	NPC486388
0.5641	Remote Similarity	NPC480553
0.5636	Remote Similarity	NPC470433
0.5636	Remote Similarity	NPC46190
0.5636	Remote Similarity	NPC171073
0.5625	Remote Similarity	NPC475182
0.5607	Remote Similarity	NPC306991
0.5603	Remote Similarity	NPC249265
0.5603	Remote Similarity	NPC480554
0.56	Remote Similarity	NPC296686
0.5586	Remote Similarity	NPC248746
0.5556	Remote Similarity	NPC23808
0.5556	Remote Similarity	NPC141433
0.5556	Remote Similarity	NPC87998
0.5545	Remote Similarity	NPC40440
0.5536	Remote Similarity	NPC42171
0.5536	Remote Similarity	NPC300557
0.5517	Remote Similarity	NPC194207
0.5517	Remote Similarity	NPC22779
0.5505	Remote Similarity	NPC14704
0.5495	Remote Similarity	NPC602423
0.547	Remote Similarity	NPC218571
0.547	Remote Similarity	NPC487615
0.5398	Remote Similarity	NPC6806
0.537	Remote Similarity	NPC295980
0.5345	Remote Similarity	NPC269297
0.5345	Remote Similarity	NPC222202
0.534	Remote Similarity	NPC181845
0.5321	Remote Similarity	NPC470432
0.5321	Remote Similarity	NPC230507
0.5299	Remote Similarity	NPC475333
0.5299	Remote Similarity	NPC13193
0.5299	Remote Similarity	NPC224098
0.5299	Remote Similarity	NPC309278
0.5299	Remote Similarity	NPC208383
0.5289	Remote Similarity	NPC232054
0.5285	Remote Similarity	NPC480556
0.5243	Remote Similarity	NPC165439
0.5207	Remote Similarity	NPC308140
0.5143	Remote Similarity	NPC272015
0.5133	Remote Similarity	NPC197231
0.5085	Remote Similarity	NPC475550
0.5047	Remote Similarity	NPC477451
0.5044	Remote Similarity	NPC19888

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC277431 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7535
0.1-0.2	1534
0.2-0.3	71
0.3-0.4	8
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8404	Intermediate Similarity	NPD8449	Approved
0.8229	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