NPASS Compound

Natural Product: NPC474399

Natural Product ID	NPC474399
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Aspaoligonin A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL466365
PubChem CID	44583985
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 117124 0 0 0 0 0 0 0 0999 V2000 -9.7525 1.3262 0.6197 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2324 -0.0762 0.3247 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8133 -0.9740 1.4513 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4439 -1.5451 1.3242 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5501 -0.8977 0.3341 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3616 -1.7663 -0.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4068 -1.6110 0.9661 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7825 -0.2499 1.5765 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9014 0.1773 0.9407 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6226 0.6298 1.0880 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4760 -0.3356 1.3632 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9638 -1.6796 0.8721 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3662 -1.9121 -0.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8542 -1.9350 -0.4511 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2233 -0.8433 0.3222 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1973 0.1670 0.8268 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3846 1.3374 -0.1438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0891 2.0964 -0.1730 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1291 1.2515 0.0059 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0520 -0.1888 -0.3693 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2509 -0.8588 0.1062 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4710 -0.3066 -0.5068 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5177 1.1343 -0.8247 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2362 1.8908 -0.7574 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5513 1.7924 -0.1140 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5346 2.3003 -0.9158 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9172 1.7423 -0.6726 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9152 2.8304 -1.0965 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7759 4.0643 -0.2347 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3597 4.0835 0.2934 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5166 3.6911 -0.7165 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0169 5.5407 0.6148 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2263 6.2674 -0.5555 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6330 4.0008 0.8797 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6324 3.2381 -2.4165 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0870 0.6032 -1.4350 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4593 -0.5005 -0.6807 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8465 -1.0027 -1.1117 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2370 -2.0405 -0.0764 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1994 -3.0996 0.0908 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7895 -2.6487 -0.0824 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5963 -1.5489 -0.8725 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0692 -2.5754 1.2635 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4627 -1.5089 2.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5236 -4.1760 -0.7374 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4369 -2.6200 -0.4527 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7726 -1.5567 -2.3818 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0541 -0.4240 -1.8710 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3122 -2.7206 1.8001 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7768 -2.5239 2.0025 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1219 -1.4444 -1.5034 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1919 -0.3286 -0.7539 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5027 -0.6499 -0.8991 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9968 1.6071 -0.1375 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6169 2.0135 0.5338 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2771 1.3834 1.6201 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3126 -0.1041 0.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6125 -1.7613 1.5484 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9377 -0.3656 2.3970 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5993 -2.6468 1.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9961 -1.5279 2.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7982 -2.8145 -0.0875 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8193 -0.2635 2.6627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5300 1.5361 1.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7270 0.8057 0.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4612 -0.4167 2.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6487 -1.1123 -1.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6667 -2.9378 -0.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4594 -2.9174 -0.1112 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5614 -1.9247 -1.5453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7875 -1.3147 1.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6703 0.6759 1.7000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6257 1.0408 -1.1582 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1318 2.0239 0.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0058 2.7092 -1.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0699 2.8702 0.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4352 1.2560 1.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2158 -1.9384 -0.0452 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2807 -0.6724 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3136 -0.5155 0.2225 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7541 -0.9643 -1.3841 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8568 1.2257 -1.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8551 2.2278 -1.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4294 2.8807 -0.2389 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2922 2.0629 -1.9906 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0937 1.5157 0.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9641 2.4841 -0.9906 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9608 4.9902 -0.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2152 3.4273 1.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6434 5.8759 1.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9264 5.5548 0.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5002 6.9118 -0.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5341 4.2256 0.5864 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3888 2.9731 -2.9783 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5527 -0.2904 0.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6010 -0.2192 -1.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4042 -1.5190 0.8871 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3020 -3.4946 1.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2617 -3.5003 -0.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3458 -3.5090 1.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9827 -2.6369 1.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3703 -1.6561 2.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4369 -4.1334 -1.0997 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1271 -1.9712 -0.6652 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1005 -1.0340 -2.8805 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7183 0.2667 -2.2993 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9822 -0.1728 -2.3726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3406 -1.4408 -2.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8595 -3.5519 1.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5923 -2.2604 2.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0658 -3.2208 2.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9428 -3.3774 1.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1541 -1.5165 -1.9889 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8452 -0.3919 -1.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5533 -2.1991 -2.0797 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9125 -0.1248 -1.7644 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7149 -1.7416 -0.8820 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 8 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 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 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 30 32 1 0 32 33 1 0 29 34 1 0 28 35 1 0 27 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 43 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 20 48 1 0 12 49 1 0 7 50 1 0 6 51 1 0 5 52 1 0 52 53 1 0 53 2 1 0 9 5 1 0 12 7 1 0 16 11 1 0 20 15 1 0 24 19 1 0 31 26 1 0 42 37 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 0 3 58 1 0 3 59 1 0 4 60 1 0 4 61 1 0 6 62 1 0 8 63 1 0 10 64 1 0 10 65 1 0 11 66 1 0 13 67 1 0 13 68 1 0 14 69 1 0 14 70 1 0 15 71 1 0 16 72 1 0 17 73 1 0 17 74 1 0 18 75 1 0 18 76 1 0 19 77 1 0 21 78 1 0 21 79 1 0 22 80 1 0 22 81 1 0 23 82 1 0 24 83 1 0 24 84 1 0 26 85 1 0 27 86 1 0 28 87 1 0 29 88 1 0 30 89 1 0 32 90 1 0 32 91 1 0 33 92 1 0 34 93 1 0 35 94 1 0 37 95 1 0 38 96 1 0 39 97 1 0 40 98 1 0 41 99 1 0 43100 1 0 43101 1 0 44102 1 0 45103 1 0 46104 1 0 47105 1 0 48106 1 0 48107 1 0 48108 1 0 49109 1 0 49110 1 0 49111 1 0 50112 1 0 51113 1 0 51114 1 0 51115 1 0 53116 1 0 53117 1 0 M END

Standard InCHIKey	FMWZYCJVASHAKM-MWJXEZMLSA-N
Standard InCHI	InChI=1S/C39H64O14/c1-18-7-12-38(48-17-18)19(2)39(47)27(53-38)14-24-22-6-5-20-13-21(8-10-36(20,3)23(22)9-11-37(24,39)4)49-35-33(31(45)29(43)26(16-41)51-35)52-34-32(46)30(44)28(42)25(15-40)50-34/h18-35,40-47H,5-17H2,1-4H3/t18-,19+,20+,21-,22+,23-,24-,25-,26+,27-,28-,29+,30-,31-,32+,33+,34-,35+,36-,37-,38+,39+/m0/s1
SMILES	CC1CCC2(C(C3(C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)O)C)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.43	Volume:	737.711 ? Van der Waals volume.
Dense:	1.025	LogP:	1.067 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.96 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.451 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	42.0
TPSA:	217.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	8.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.174	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.329	Fsp³:	1.0
MCE-18:	207.692 ? 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:	0.004	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.042 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.14 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.244	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.566	MDCK Permeability:	-4.82
Pgp-inhibitor:	0.0	Pgp-substrate:	0.455
PAMPA:	0.998 ? 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):	0.875
20% Bioavailability (F20%):	0.087	30% Bioavailability (F30%):	0.968
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16	MRP1:	1.0
Plasma Protein Binding (PPB):	61.906%	Volume Distribution (VD):	-0.41
Fu:	26.286% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.05	BCRP inhibitor:	0.002
BSEP inhibitor:	0.504

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.866	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.019	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.017	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

1.704

Half-life (T1/2):

3.201

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.514
Human Hepatotoxicity (H-HT):	0.602	Drug-induced Liver Injury (DILI):	0.2
AMES Toxicity:	0.363	Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.36	Skin Sensitization:	0.041
Carcinogencity:	0.195	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.04
Drug-induced Neurotoxicity:	0.422	Ototoxicity:	0.999
Hematotoxicity:	0.015	Drug-induced Nephrotoxicity:	0.012
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.11
A549 Cytotoxicity:	0.072	Hek293 Cytotoxicity:	0.746
BCF:	1.595 ? 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:	4.095 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.784 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.701 ? 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
NPO32947	asparagus oligoclonos	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[15921426]

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	5

Activity Type	# Activity
Cell line	5

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
NPT81	Cell line	A549	Homo sapiens	IC50	=	2.25	ug.mL-1	PMID[19856955]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	2.66	ug.mL-1	PMID[21084196]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	=	2.53	ug.mL-1	PMID[23357036]
NPT574	Cell line	XF498	Homo sapiens	IC50	=	2.84	ug.mL-1	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	2.59	ug.mL-1	PubChem BioAssay data set

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 NPC474399 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	27383
0.1-0.2	19181
0.2-0.3	2585
0.3-0.4	532
0.4-0.5	131
0.5-0.6	33
0.6-0.7	4
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
0.734	Intermediate Similarity	NPC40440
0.7292	Intermediate Similarity	NPC274200
0.7159	Intermediate Similarity	NPC297348
0.7159	Intermediate Similarity	NPC249204
0.7159	Intermediate Similarity	NPC48339
0.7159	Intermediate Similarity	NPC141769
0.7159	Intermediate Similarity	NPC477547
0.6813	Remote Similarity	NPC477451
0.6458	Remote Similarity	NPC107962
0.6421	Remote Similarity	NPC211354
0.6117	Remote Similarity	NPC124677
0.5979	Remote Similarity	NPC206003
0.5979	Remote Similarity	NPC473610
0.59	Remote Similarity	NPC6295
0.5865	Remote Similarity	NPC92890
0.5833	Remote Similarity	NPC294686
0.5833	Remote Similarity	NPC291203
0.5833	Remote Similarity	NPC217205
0.5825	Remote Similarity	NPC42482
0.5784	Remote Similarity	NPC160426
0.567	Remote Similarity	NPC234352
0.5657	Remote Similarity	NPC128123
0.56	Remote Similarity	NPC19400
0.5577	Remote Similarity	NPC475351
0.5567	Remote Similarity	NPC325828
0.5566	Remote Similarity	NPC469348
0.5556	Remote Similarity	NPC292467
0.5556	Remote Similarity	NPC222731
0.5472	Remote Similarity	NPC469347
0.5463	Remote Similarity	NPC128572
0.5405	Remote Similarity	NPC475625
0.5333	Remote Similarity	NPC113044
0.5333	Remote Similarity	NPC283829
0.5333	Remote Similarity	NPC161676
0.5327	Remote Similarity	NPC475643
0.5294	Remote Similarity	NPC107188
0.5273	Remote Similarity	NPC184617
0.5149	Remote Similarity	NPC210157
0.5143	Remote Similarity	NPC125324
0.5135	Remote Similarity	NPC97700
0.5135	Remote Similarity	NPC30856
0.5128	Remote Similarity	NPC167183
0.5094	Remote Similarity	NPC141433
0.5089	Remote Similarity	NPC475319

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474399 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7863
0.1-0.2	1213
0.2-0.3	61
0.3-0.4	10
0.4-0.5	1
0.5-0.6	1
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
0.5567	Remote Similarity	NPD8171	Phase 2

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