NPASS Compound

Natural Product: NPC177834

Natural Product ID	NPC177834
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Filiasparoside D
IUPAC Name	n.a.
Synonyms	filiasparoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL400885
PubChem CID	23624759
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 112119 0 0 0 0 0 0 0 0999 V2000 -11.2895 -0.1964 -2.2367 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4008 -0.9505 -1.2385 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1143 -1.2576 -1.9755 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1219 -0.1755 -1.6009 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7574 -0.4279 -0.1351 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9089 0.6657 0.4439 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6809 1.5497 1.3962 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8956 -0.1184 1.2900 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8293 -1.4108 0.4658 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6825 -1.0337 -0.4916 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7253 -0.5640 0.5143 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4720 0.0776 0.1492 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6042 -0.5848 -0.8629 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5611 0.4707 -1.2658 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1207 1.2872 -0.1051 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3070 1.7099 -0.2956 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2856 0.5873 -0.2154 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7205 -0.6760 0.3904 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7432 -0.4581 1.4758 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2864 0.6057 1.2401 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0033 1.7114 2.2709 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6640 0.1089 1.4617 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4024 0.7828 2.5677 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8668 0.5821 2.6098 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5473 0.4868 1.2827 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4757 1.8354 0.6202 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5122 0.9258 0.3479 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5752 0.8224 -0.5199 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3676 2.1027 -0.6601 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6951 2.5784 0.7287 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0753 1.4217 1.6203 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4457 0.2329 0.7442 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8840 -0.9030 1.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2830 -2.0310 1.0004 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3609 -1.8811 0.1676 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4179 -2.9594 0.3562 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0269 -3.3385 -1.0012 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1791 -2.0573 -1.7838 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8009 -1.4752 -1.9982 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8780 -2.0806 -1.1483 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7240 -2.3486 -3.0336 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0698 -4.1145 -1.6703 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4278 -2.4495 1.1399 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3995 -0.1878 -0.0327 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2486 1.7860 2.2967 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4930 3.1065 1.2539 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4701 1.9089 -1.4646 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0181 -1.5982 -0.1340 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9209 -0.5030 0.5945 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0459 -0.0431 -0.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7430 0.7077 -2.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4694 -0.8226 -3.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2632 0.0482 -1.7475 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9188 -1.8576 -0.8964 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7378 -2.2292 -1.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2672 -1.3162 -3.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1982 -0.3805 -2.2167 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4926 0.8304 -1.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4336 1.2020 -0.3837 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1678 1.6632 2.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8135 2.5262 0.8847 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6783 1.0871 1.6545 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3260 -0.2848 2.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4899 -2.2009 1.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0206 -0.1994 -1.1279 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3580 -1.9257 -1.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5316 -1.4013 1.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5716 1.1628 -0.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1873 -0.8543 -1.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0735 -1.4255 -0.4164 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1469 1.1624 -1.9456 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2248 0.0557 -1.8975 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7180 2.2446 -0.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4953 2.5354 0.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3437 2.2222 -1.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5293 0.3081 -1.2774 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3302 -1.3933 -0.3474 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6113 -1.2033 0.8469 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2899 -0.3259 2.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1899 -1.4306 1.6236 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3569 2.6898 1.9056 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1240 1.7944 2.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2961 1.4432 3.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5965 -0.9841 1.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1931 1.8710 2.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9928 0.3512 3.5319 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3241 1.3898 3.2245 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1050 -0.3721 3.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6436 2.4252 1.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4112 2.3926 0.9222 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4841 1.7994 -0.4710 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2871 0.5013 -1.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7481 2.8864 -1.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4601 3.3843 0.7103 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3285 1.1714 2.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3578 0.5362 0.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6982 -0.5388 2.3488 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0527 -1.1776 2.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8019 -0.8647 0.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0033 -3.8749 0.7816 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9613 -3.8622 -0.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8552 -1.3427 -1.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8803 -0.3777 -1.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4874 -1.4949 -3.0571 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1761 -1.5534 -3.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4831 -4.4412 -2.5067 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1316 -2.5268 2.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1160 1.8418 3.2691 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6491 3.9058 1.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2445 2.0219 -2.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9632 1.0242 -0.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8828 -0.0454 0.6714 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 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 1 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 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 37 42 1 0 36 43 1 0 32 44 1 0 31 45 1 0 30 46 1 0 29 47 1 0 9 48 1 0 5 49 1 1 49 50 1 0 50 2 1 0 48 5 1 0 25 8 1 0 44 28 1 0 25 11 1 0 40 35 1 0 22 12 1 0 20 15 1 0 1 51 1 0 1 52 1 0 1 53 1 0 2 54 1 1 3 55 1 0 3 56 1 0 4 57 1 0 4 58 1 0 6 59 1 6 7 60 1 0 7 61 1 0 7 62 1 0 8 63 1 1 9 64 1 1 10 65 1 0 10 66 1 0 11 67 1 1 12 68 1 6 13 69 1 0 13 70 1 0 14 71 1 0 14 72 1 0 15 73 1 1 16 74 1 0 16 75 1 0 17 76 1 6 18 77 1 0 18 78 1 0 19 79 1 0 19 80 1 0 21 81 1 0 21 82 1 0 21 83 1 0 22 84 1 1 23 85 1 0 23 86 1 0 24 87 1 0 24 88 1 0 26 89 1 0 26 90 1 0 26 91 1 0 28 92 1 6 29 93 1 6 30 94 1 6 31 95 1 1 32 96 1 6 33 97 1 0 33 98 1 0 35 99 1 6 36100 1 1 37101 1 1 38102 1 1 39103 1 0 39104 1 0 41105 1 0 42106 1 0 43107 1 0 45108 1 0 46109 1 0 47110 1 0 50111 1 0 50112 1 0 M END

Standard InCHIKey	OSHZDTNWJYPSSP-JSYHJTIVSA-N
Standard InCHI	InChI=1S/C38H62O12/c1-18-7-12-38(47-15-18)19(2)28-26(50-38)14-24-22-6-5-20-13-21(8-10-36(20,3)23(22)9-11-37(24,28)4)48-35-33(44)31(42)30(41)27(49-35)17-46-34-32(43)29(40)25(39)16-45-34/h18-35,39-44H,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+/m0/s1
SMILES	C[C@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC[C@@H]6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]4[C@@H]([C@H]([C@H](CO4)O)O)O)O3)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.42	Volume:	702.835 ? Van der Waals volume.
Dense:	1.011	LogP:	3.359 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.896 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.476 ? 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:	0.23	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.178	Fsp³:	1.0
MCE-18:	197.289 ? 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:	0.738	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.065 ? 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:	0.185	Promiscuous compounds:	0.01

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.861	MDCK Permeability:	-5.049
Pgp-inhibitor:	0.055	Pgp-substrate:	0.427
PAMPA:	0.833 ? 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%):	0.024	30% Bioavailability (F30%):	0.839
50% Bioavailability (F50%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.096
Plasma Protein Binding (PPB):	63.91%	Volume Distribution (VD):	-0.399
Fu:	29.174% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.447
BSEP inhibitor:	0.693

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.036	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.792
HLM stability:	0.003 ? 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):

1.431

Half-life (T1/2):

2.102

ADMET: Toxicity

hERG Blockers:	0.046	hERG Blockers (10um):	0.228
Human Hepatotoxicity (H-HT):	0.556	Drug-induced Liver Injury (DILI):	0.916
AMES Toxicity:	0.844	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.102	Skin Sensitization:	1.0
Carcinogencity:	0.206	Eye Corrosion:	0.0
Eye Irritation:	0.029	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.961
Hematotoxicity:	0.146	Drug-induced Nephrotoxicity:	0.595
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.203
A549 Cytotoxicity:	0.878	Hek293 Cytotoxicity:	0.868
BCF:	2.305 ? 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:	3.702 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.647 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.302 ? 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
NPO4755	Asparagus filicinus	Species	Asparagaceae	Eukaryota	Roots	n.a.	n.a.	PMID[17629328]
NPO4755	Asparagus filicinus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4755	Asparagus filicinus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4755	Asparagus filicinus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4755	Asparagus filicinus	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

Activity Type	# Activity
EC50	2

Activity Type	# Activity
Cell line	2

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	EC50	=	2.4	ug.mL-1	PMID[16124773]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	10.3	ug.mL-1	PMID[26003344]

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 NPC177834 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	25452
0.1-0.2	21278
0.2-0.3	2542
0.3-0.4	357
0.4-0.5	119
0.5-0.6	72
0.6-0.7	23
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	Natural Product ID
0.8235	Intermediate Similarity	NPC215408
0.7765	Intermediate Similarity	NPC250393
0.75	Intermediate Similarity	NPC264101
0.7386	Intermediate Similarity	NPC211354
0.7263	Intermediate Similarity	NPC128572
0.7191	Intermediate Similarity	NPC107188
0.7126	Intermediate Similarity	NPC234352
0.7097	Intermediate Similarity	NPC475351
0.7011	Intermediate Similarity	NPC297348
0.7011	Intermediate Similarity	NPC325828
0.7011	Intermediate Similarity	NPC249204
0.7011	Intermediate Similarity	NPC48339
0.7011	Intermediate Similarity	NPC141769
0.7011	Intermediate Similarity	NPC477547
0.6854	Remote Similarity	NPC477451
0.6842	Remote Similarity	NPC202898
0.6837	Remote Similarity	NPC97700
0.6837	Remote Similarity	NPC30856
0.6667	Remote Similarity	NPC107962
0.6634	Remote Similarity	NPC475625
0.6633	Remote Similarity	NPC471464
0.6632	Remote Similarity	NPC160426
0.6569	Remote Similarity	NPC232037
0.6538	Remote Similarity	NPC132080
0.6522	Remote Similarity	NPC206003
0.6522	Remote Similarity	NPC473610
0.6452	Remote Similarity	NPC19400
0.6311	Remote Similarity	NPC116756
0.63	Remote Similarity	NPC51172
0.63	Remote Similarity	NPC49032
0.625	Remote Similarity	NPC481418
0.625	Remote Similarity	NPC6295
0.6222	Remote Similarity	NPC485594
0.61	Remote Similarity	NPC475643
0.6055	Remote Similarity	NPC470866
0.6019	Remote Similarity	NPC184617
0.6	Remote Similarity	NPC473601
0.5962	Remote Similarity	NPC475319
0.5917	Remote Similarity	NPC329807
0.5909	Remote Similarity	NPC88962
0.5889	Remote Similarity	NPC473774
0.5889	Remote Similarity	NPC481419
0.5889	Remote Similarity	NPC481417
0.5851	Remote Similarity	NPC294686
0.5806	Remote Similarity	NPC181845
0.578	Remote Similarity	NPC233433
0.5758	Remote Similarity	NPC125324
0.5729	Remote Similarity	NPC222731
0.5726	Remote Similarity	NPC329727
0.5688	Remote Similarity	NPC476112
0.5688	Remote Similarity	NPC307534
0.566	Remote Similarity	NPC115165
0.5652	Remote Similarity	NPC24960
0.5645	Remote Similarity	NPC481189
0.56	Remote Similarity	NPC485595
0.5596	Remote Similarity	NPC470864
0.5577	Remote Similarity	NPC92890
0.5575	Remote Similarity	NPC94086
0.5575	Remote Similarity	NPC473817
0.5565	Remote Similarity	NPC220836
0.5556	Remote Similarity	NPC475333
0.5556	Remote Similarity	NPC48463
0.5556	Remote Similarity	NPC144790
0.5556	Remote Similarity	NPC149400
0.5556	Remote Similarity	NPC248944
0.5556	Remote Similarity	NPC7479
0.5556	Remote Similarity	NPC257296
0.5556	Remote Similarity	NPC224098
0.5556	Remote Similarity	NPC208383
0.5545	Remote Similarity	NPC83137
0.5545	Remote Similarity	NPC70204
0.5543	Remote Similarity	NPC481420
0.5543	Remote Similarity	NPC481421
0.549	Remote Similarity	NPC14704
0.5474	Remote Similarity	NPC481423
0.5446	Remote Similarity	NPC470432
0.5446	Remote Similarity	NPC230507
0.5421	Remote Similarity	NPC294129
0.5408	Remote Similarity	NPC312678
0.5408	Remote Similarity	NPC253268
0.5361	Remote Similarity	NPC485591
0.534	Remote Similarity	NPC113044
0.534	Remote Similarity	NPC283829
0.534	Remote Similarity	NPC161676
0.5327	Remote Similarity	NPC151134
0.5326	Remote Similarity	NPC277715
0.5317	Remote Similarity	NPC329820
0.5315	Remote Similarity	NPC108072
0.53	Remote Similarity	NPC306131
0.53	Remote Similarity	NPC200802
0.5285	Remote Similarity	NPC330026
0.5259	Remote Similarity	NPC480556
0.5248	Remote Similarity	NPC485590
0.5243	Remote Similarity	NPC195297
0.5225	Remote Similarity	NPC232611
0.5204	Remote Similarity	NPC131693
0.5204	Remote Similarity	NPC475436
0.5181	Remote Similarity	NPC227260
0.5155	Remote Similarity	NPC481424
0.5155	Remote Similarity	NPC481422
0.5149	Remote Similarity	NPC54619
0.514	Remote Similarity	NPC477809
0.5135	Remote Similarity	NPC473518
0.5102	Remote Similarity	NPC13190
0.5093	Remote Similarity	NPC274200
0.5047	Remote Similarity	NPC470433
0.5047	Remote Similarity	NPC46190
0.5047	Remote Similarity	NPC171073
0.5047	Remote Similarity	NPC602423

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC177834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7646
0.1-0.2	1430
0.2-0.3	60
0.3-0.4	9
0.4-0.5	1
0.5-0.6	3
0.6-0.7	0
0.7-0.8	1
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
0.7011	Intermediate Similarity	NPD8171	Phase 2
0.5918	Remote Similarity	NPD8170	Phase 2
0.5556	Remote Similarity	NPD6928	Phase 2
0.5269	Remote Similarity	NPD7991	Discontinued

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