NPASS Compound

Natural Product: NPC271580

Natural Product ID	NPC271580
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UPNUGXGHDWZCLI-NOOOHJCFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	23304979
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 113120 0 0 0 0 0 0 0 0999 V2000 11.0772 -1.2148 0.8606 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7918 0.1714 0.3654 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8646 0.9458 1.2965 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5804 0.2050 1.3696 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9932 -0.2082 0.0645 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9517 0.8104 -0.3378 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4421 1.7673 -1.3886 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8672 -0.0345 -0.9632 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4960 0.3513 -0.5280 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6663 1.0332 -1.5856 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2706 1.1834 -1.0152 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6528 -0.1690 -0.7707 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1972 -0.1037 -0.4487 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1074 1.2305 0.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6323 -0.1352 -1.7285 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5992 -1.2756 -1.7630 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5035 -1.2648 -0.5353 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7020 -1.2778 0.7566 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2716 -1.2532 0.3607 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5040 -2.2521 0.7393 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9274 -2.3091 0.3812 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4703 -0.9217 0.2568 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4421 -0.2826 1.6186 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8448 -1.0135 -0.3164 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8736 -1.7124 0.4834 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1249 -1.3803 -0.3492 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2734 -1.3888 0.3407 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2323 -0.0915 -0.5675 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6002 -0.3233 -0.6888 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2745 0.2618 0.5322 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8117 1.7000 0.6591 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4200 2.2498 -0.6732 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1885 1.6186 -1.8105 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6856 2.2400 -3.1125 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3652 1.9050 -3.3578 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1093 0.2480 -1.8531 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7631 3.6128 -0.6775 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6930 1.6893 1.5045 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6467 0.1868 0.2984 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3383 -0.5618 1.2227 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3624 0.3065 1.8993 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5526 0.5716 1.0018 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1501 -0.7227 0.5430 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2233 -1.8707 0.8851 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6832 -3.1007 0.1405 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9165 -1.6294 0.5385 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4978 -0.7181 -0.7964 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4693 1.3261 1.7504 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7232 -0.1477 3.1476 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8685 -0.5146 -0.9300 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0555 0.1328 -0.9689 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1698 -1.4580 0.7178 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7772 -1.3387 1.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5541 -1.9592 0.1922 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7427 0.6956 0.1913 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3542 0.8911 2.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7990 1.9741 0.9150 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7890 0.7855 1.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7564 -0.6895 2.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5682 1.3986 0.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1338 2.5425 -0.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5489 2.3361 -1.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8462 1.2555 -2.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9149 -0.0456 -2.0703 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5659 0.9350 0.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6529 0.3964 -2.4777 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0570 2.0539 -1.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3522 1.7396 -0.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 1.7574 -1.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7637 -0.7461 -1.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6104 1.5268 0.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1397 1.9796 -0.6359 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1172 1.2569 0.6568 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1701 0.8034 -1.9159 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0659 -0.2738 -2.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0918 -2.2484 -1.8696 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2572 -1.1322 -2.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1783 -2.1462 -0.6092 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9869 -0.4702 1.4326 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9644 -2.2362 1.2873 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0762 -3.0508 1.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5467 -2.8547 1.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0873 -2.8334 -0.5953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1824 -0.8680 2.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7728 0.7521 1.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4854 -0.3842 2.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7708 -1.4865 -1.3173 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0409 -1.1683 1.4558 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7433 -2.7837 0.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1526 -2.1448 -1.1601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7558 -1.4179 -0.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0510 -0.3171 1.4335 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5900 2.3274 1.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3166 2.2273 -0.8365 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2509 1.9827 -1.7028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3306 1.8990 -3.9590 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7584 3.3402 -3.0837 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7665 2.6409 -3.0441 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6542 3.7519 -1.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3574 2.6053 1.6541 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6573 -0.9700 1.9988 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8736 1.3114 2.0537 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2313 1.1747 0.1330 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0816 -0.8858 1.1313 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3408 -2.0698 1.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0964 -3.1919 -0.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4096 -3.9810 0.7746 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7692 -3.0702 -0.0864 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7916 -1.1085 -1.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0119 1.8595 1.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0669 0.5552 3.7310 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7391 -0.4504 -1.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0563 1.1559 -1.3533 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 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 17 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 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 43 47 1 0 42 48 1 0 41 49 1 0 5 50 1 6 50 51 1 0 51 2 1 0 27 5 1 0 36 29 1 0 46 40 1 0 26 8 1 0 24 9 1 0 22 12 1 0 19 13 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 6 3 56 1 0 3 57 1 0 4 58 1 0 4 59 1 0 6 60 1 1 7 61 1 0 7 62 1 0 7 63 1 0 8 64 1 6 9 65 1 1 10 66 1 0 10 67 1 0 11 68 1 0 11 69 1 0 12 70 1 6 14 71 1 0 14 72 1 0 14 73 1 0 15 74 1 0 15 75 1 0 16 76 1 0 16 77 1 0 17 78 1 6 18 79 1 0 18 80 1 0 20 81 1 0 21 82 1 0 21 83 1 0 23 84 1 0 23 85 1 0 23 86 1 0 24 87 1 6 25 88 1 0 25 89 1 0 26 90 1 6 29 91 1 6 30 92 1 1 31 93 1 1 32 94 1 6 33 95 1 1 34 96 1 0 34 97 1 0 35 98 1 0 37 99 1 0 38100 1 0 40101 1 1 41102 1 1 42103 1 6 43104 1 1 44105 1 1 45106 1 0 45107 1 0 45108 1 0 47109 1 0 48110 1 0 49111 1 0 51112 1 0 51113 1 0 M END

Standard InCHIKey	UPNUGXGHDWZCLI-NOOOHJCFSA-N
Standard InCHI	InChI=1S/C39H62O12/c1-18-8-13-39(46-17-18)19(2)28-23-6-7-27-37(4)12-10-22(14-21(37)9-11-38(27,5)24(23)15-25(28)51-39)48-36-34(32(44)30(42)26(16-40)49-36)50-35-33(45)31(43)29(41)20(3)47-35/h9,18-20,22-36,40-45H,6-8,10-17H2,1-5H3/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]4CC[C@@H]5[C@@]6(C)CC[C@@H](CC6=CC[C@@]5(C)[C@@H]4C[C@@H]3O2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@@H](C)O2)O)O)O)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	722.42	Volume:	717.494 ? Van der Waals volume.
Dense:	1.007	LogP:	2.866 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.592 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.3 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.229	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.406	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:	0.795	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:	0.15	Promiscuous compounds:	0.016

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.119	MDCK Permeability:	-5.099
Pgp-inhibitor:	0.001	Pgp-substrate:	0.128
PAMPA:	0.994 ? 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):	0.001
20% Bioavailability (F20%):	0.287	30% Bioavailability (F30%):	0.743
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.061
Plasma Protein Binding (PPB):	70.067%	Volume Distribution (VD):	-0.384
Fu:	25.238% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.161
BSEP inhibitor:	0.747

ADMET: Metabolism

CYP1A2-inhibitor:	0.347	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.976	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.111	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.018	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.846
HLM stability:	0.454 ? 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):

1.467

Half-life (T1/2):

2.077

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.064
Human Hepatotoxicity (H-HT):	0.499	Drug-induced Liver Injury (DILI):	0.966
AMES Toxicity:	0.896	Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.03	Skin Sensitization:	1.0
Carcinogencity:	0.332	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.993
Hematotoxicity:	0.322	Drug-induced Nephrotoxicity:	0.925
Genotoxicity:	0.017	RPMI-8226 Immunitoxicity:	0.187
A549 Cytotoxicity:	0.886	Hek293 Cytotoxicity:	0.841
BCF:	2.189 ? 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:	3.867 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.088 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.514 ? 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
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13117	Asparagus setaceus	Species	Asparagaceae	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 NPC271580 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	23495
0.1-0.2	22693
0.2-0.3	2851
0.3-0.4	623
0.4-0.5	122
0.5-0.6	43
0.6-0.7	25
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	Natural Product ID
0.7579	Intermediate Similarity	NPC113044
0.7579	Intermediate Similarity	NPC283829
0.7579	Intermediate Similarity	NPC161676
0.6939	Remote Similarity	NPC141433
0.6737	Remote Similarity	NPC477451
0.6476	Remote Similarity	NPC480555
0.6476	Remote Similarity	NPC150372
0.6442	Remote Similarity	NPC477809
0.6354	Remote Similarity	NPC297348
0.6354	Remote Similarity	NPC249204
0.6354	Remote Similarity	NPC48339
0.6354	Remote Similarity	NPC141769
0.6354	Remote Similarity	NPC477547
0.6346	Remote Similarity	NPC470433
0.6346	Remote Similarity	NPC46190
0.6346	Remote Similarity	NPC171073
0.625	Remote Similarity	NPC40440
0.6226	Remote Similarity	NPC300557
0.6214	Remote Similarity	NPC305423
0.619	Remote Similarity	NPC602423
0.6162	Remote Similarity	NPC222731
0.6161	Remote Similarity	NPC480553
0.6126	Remote Similarity	NPC480554
0.6091	Remote Similarity	NPC13193
0.6082	Remote Similarity	NPC181845
0.6058	Remote Similarity	NPC14704
0.6	Remote Similarity	NPC269297
0.6	Remote Similarity	NPC222202
0.5946	Remote Similarity	NPC475333
0.5946	Remote Similarity	NPC224098
0.5946	Remote Similarity	NPC208383
0.5865	Remote Similarity	NPC470432
0.5865	Remote Similarity	NPC230507
0.5833	Remote Similarity	NPC248746
0.58	Remote Similarity	NPC294686
0.5794	Remote Similarity	NPC98696
0.5769	Remote Similarity	NPC107962
0.5763	Remote Similarity	NPC480556
0.5752	Remote Similarity	NPC194207
0.5752	Remote Similarity	NPC22779
0.5728	Remote Similarity	NPC211354
0.5714	Remote Similarity	NPC6295
0.5577	Remote Similarity	NPC306131
0.5577	Remote Similarity	NPC200802
0.5577	Remote Similarity	NPC19400
0.5526	Remote Similarity	NPC309278
0.5508	Remote Similarity	NPC232054
0.5495	Remote Similarity	NPC42171
0.5455	Remote Similarity	NPC224314
0.5421	Remote Similarity	NPC485595
0.5413	Remote Similarity	NPC19888
0.5405	Remote Similarity	NPC92890
0.5364	Remote Similarity	NPC197231
0.5357	Remote Similarity	NPC6806
0.5347	Remote Similarity	NPC485594
0.5278	Remote Similarity	NPC306991
0.5259	Remote Similarity	NPC32361
0.5238	Remote Similarity	NPC474399
0.5229	Remote Similarity	NPC195297
0.5225	Remote Similarity	NPC486388
0.5221	Remote Similarity	NPC124677
0.5189	Remote Similarity	NPC206003
0.5189	Remote Similarity	NPC473610
0.5182	Remote Similarity	NPC160426
0.5175	Remote Similarity	NPC475182
0.5172	Remote Similarity	NPC475550
0.5161	Remote Similarity	NPC477808
0.514	Remote Similarity	NPC54619
0.5083	Remote Similarity	NPC477811
0.5048	Remote Similarity	NPC234352
0.5045	Remote Similarity	NPC600116

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC271580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7601
0.1-0.2	1486
0.2-0.3	54
0.3-0.4	5
0.4-0.5	4
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