NPASS Compound

Natural Product: NPC215408

Natural Product ID	NPC215408
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Filiasparoside B
IUPAC Name	n.a.
Synonyms	filiasparoside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL251512
PubChem CID	23624757
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 111118 0 0 0 0 0 0 0 0999 V2000 -9.9696 1.2785 -1.0230 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4955 -0.0743 -0.6304 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1057 -0.4535 0.7781 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0307 -1.5031 0.8318 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9953 -1.1585 -0.2392 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7664 -2.0510 -0.0777 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9562 -3.3683 -0.7931 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6948 -1.2074 -0.7070 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2563 0.1914 -0.5640 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2196 0.9534 0.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9690 0.2401 -0.1758 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7670 0.5161 0.6252 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3749 1.9863 0.5590 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2023 2.1325 1.4989 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0562 1.3548 0.8665 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2579 1.7207 1.5055 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3580 1.0179 0.7536 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1113 -0.5053 0.8155 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7802 -0.8258 0.1748 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3602 -0.1200 0.8619 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4918 -0.7024 2.2356 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6338 -0.3172 0.0679 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9356 -1.7553 -0.1071 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3306 -2.0203 -0.5542 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5233 -2.8876 -1.3750 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 -1.2023 0.0383 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5323 -1.5950 1.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6206 1.2148 1.2689 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5532 1.6571 0.3390 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9938 3.0809 0.6014 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8731 3.1240 1.8445 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3562 1.7005 2.1308 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6928 1.0256 0.8120 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4901 -0.2480 1.0714 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8890 -0.8982 -0.0575 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7031 -0.2232 -0.9237 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9700 -0.9721 -1.2647 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7483 -1.8425 -2.4874 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5477 -0.8867 -3.6657 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8327 0.3325 -3.1423 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9846 -0.0541 -2.1081 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7765 -1.4874 -4.6596 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6570 -2.6807 -2.3339 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0032 -0.0875 -1.5671 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5602 0.7766 0.1059 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4907 1.6940 2.9388 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2476 3.6177 2.9586 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7345 3.5847 -0.4569 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4552 0.0751 0.1181 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5245 -1.1775 -1.5047 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8945 -1.1001 -1.5673 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7366 1.9169 -0.1461 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7801 1.7940 -1.6024 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1265 1.1915 -1.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6016 -0.1155 -0.7760 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7466 0.4462 1.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0130 -0.7812 1.3668 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5056 -1.3875 1.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4122 -2.5352 0.6966 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6672 -2.1807 1.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9614 -3.3546 -1.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8792 -4.2457 -0.1210 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2300 -3.4990 -1.6217 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5946 -1.5072 -1.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4041 0.6195 -1.5882 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4495 0.8554 1.2990 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2136 2.0347 -0.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8252 0.3976 -1.2608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9680 0.3269 1.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2289 2.5458 0.9880 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1765 2.3275 -0.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 1.6881 2.4714 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8727 3.1862 1.5977 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0132 1.6838 -0.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2746 1.5391 2.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3475 2.8289 1.3907 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2490 1.2585 -0.3134 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9961 -0.7540 1.8903 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9423 -1.0818 0.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8506 -0.6087 -0.8903 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6601 -1.9356 0.2729 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2294 -1.8002 2.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2514 -0.2702 2.9520 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4666 -0.6035 2.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4286 0.1076 -0.9502 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2561 -2.1831 -0.8723 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7092 -2.3552 0.8215 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2965 -1.0707 2.0421 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7744 -2.7013 1.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5131 -1.5939 1.9586 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9701 1.7241 -0.6351 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1514 3.7691 0.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7674 3.7243 1.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5704 1.1269 2.6576 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3505 1.7856 0.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3337 -0.0250 1.7924 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8119 -0.9197 1.6350 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9538 0.8185 -0.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3298 -1.5971 -0.4227 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6343 -2.4629 -2.7021 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5331 -0.6646 -4.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1639 0.7813 -3.9308 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5176 1.1610 -2.8648 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0201 -2.4348 -4.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3081 -2.7436 -1.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9923 0.6783 -0.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3950 2.2494 3.7399 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7156 2.9087 3.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7348 2.9957 -1.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1532 -0.8624 -2.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4013 -2.0663 -1.3629 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 2 0 24 26 1 0 26 27 1 1 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 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 33 45 1 0 32 46 1 0 31 47 1 0 30 48 1 0 9 49 1 0 5 50 1 6 50 51 1 0 51 2 1 0 49 5 1 0 26 8 1 0 45 29 1 0 26 11 1 0 41 36 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 1 7 61 1 0 7 62 1 0 7 63 1 0 8 64 1 6 9 65 1 6 10 66 1 0 10 67 1 0 11 68 1 6 12 69 1 1 13 70 1 0 13 71 1 0 14 72 1 0 14 73 1 0 15 74 1 6 16 75 1 0 16 76 1 0 17 77 1 6 18 78 1 0 18 79 1 0 19 80 1 0 19 81 1 0 21 82 1 0 21 83 1 0 21 84 1 0 22 85 1 6 23 86 1 0 23 87 1 0 27 88 1 0 27 89 1 0 27 90 1 0 29 91 1 6 30 92 1 1 31 93 1 6 32 94 1 1 33 95 1 6 34 96 1 0 34 97 1 0 36 98 1 1 37 99 1 1 38100 1 6 39101 1 6 40102 1 0 40103 1 0 42104 1 0 43105 1 0 44106 1 0 46107 1 0 47108 1 0 48109 1 0 51110 1 0 51111 1 0 M END

Standard InCHIKey	FCNOIVRGSFYSAL-KTBMJHRNSA-N
Standard InCHI	InChI=1S/C38H60O13/c1-17-7-10-38(48-14-17)18(2)28-25(51-38)12-23-21-6-5-19-11-20(8-9-36(19,3)22(21)13-27(40)37(23,28)4)49-35-33(45)31(43)30(42)26(50-35)16-47-34-32(44)29(41)24(39)15-46-34/h17-26,28-35,39,41-45H,5-16H2,1-4H3/t17-,18+,19+,20+,21-,22+,23+,24+,25+,26-,28+,29+,30-,31+,32-,33-,34+,35-,36+,37-,38-/m1/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(=O)[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:	724.4	Volume:	708.989 ? Van der Waals volume.
Dense:	1.022	LogP:	2.201 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.921 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.037 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	43.0
TPSA:	193.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.222	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.299	Fsp³:	0.974
MCE-18:	200.373 ? 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:	0.723	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? 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:	0.144	Promiscuous compounds:	0.139

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.833	MDCK Permeability:	-5.094
Pgp-inhibitor:	0.017	Pgp-substrate:	0.465
PAMPA:	0.958 ? 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):	0.005
20% Bioavailability (F20%):	0.031	30% Bioavailability (F30%):	0.906
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.026
Plasma Protein Binding (PPB):	51.085%	Volume Distribution (VD):	-0.478
Fu:	45.048% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.914
BSEP inhibitor:	0.766

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.351	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.827 ? 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):

1.448

Half-life (T1/2):

2.213

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.239
Human Hepatotoxicity (H-HT):	0.589	Drug-induced Liver Injury (DILI):	0.982
AMES Toxicity:	0.914	Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.163	Skin Sensitization:	1.0
Carcinogencity:	0.186	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.031
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.978
Hematotoxicity:	0.176	Drug-induced Nephrotoxicity:	0.685
Genotoxicity:	0.017	RPMI-8226 Immunitoxicity:	0.272
A549 Cytotoxicity:	0.932	Hek293 Cytotoxicity:	0.933
BCF:	1.823 ? 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:	4.647 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.143 ? 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	=	16.4	ug.mL-1	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	16.8	ug.mL-1	PMID[20346682]

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 NPC215408 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	23562
0.1-0.2	23284
0.2-0.3	2558
0.3-0.4	293
0.4-0.5	104
0.5-0.6	41
0.6-0.7	10
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	Natural Product ID
0.8352	Intermediate Similarity	NPC202898
0.8235	Intermediate Similarity	NPC177834
0.73	Intermediate Similarity	NPC475319
0.7048	Intermediate Similarity	NPC233433
0.69	Remote Similarity	NPC92890
0.6789	Remote Similarity	NPC94086
0.6789	Remote Similarity	NPC473817
0.6757	Remote Similarity	NPC220836
0.6542	Remote Similarity	NPC108072
0.6458	Remote Similarity	NPC250393
0.6263	Remote Similarity	NPC264101
0.6162	Remote Similarity	NPC211354
0.6132	Remote Similarity	NPC128572
0.6	Remote Similarity	NPC107188
0.5962	Remote Similarity	NPC475351
0.5918	Remote Similarity	NPC234352
0.5909	Remote Similarity	NPC161035
0.5909	Remote Similarity	NPC170438
0.5816	Remote Similarity	NPC297348
0.5816	Remote Similarity	NPC325828
0.5816	Remote Similarity	NPC249204
0.5816	Remote Similarity	NPC48339
0.5816	Remote Similarity	NPC141769
0.5816	Remote Similarity	NPC477547
0.578	Remote Similarity	NPC97700
0.578	Remote Similarity	NPC30856
0.57	Remote Similarity	NPC477451
0.5625	Remote Similarity	NPC475625
0.5596	Remote Similarity	NPC471464
0.5577	Remote Similarity	NPC107962
0.5575	Remote Similarity	NPC232037
0.5566	Remote Similarity	NPC160426
0.5565	Remote Similarity	NPC132080
0.5437	Remote Similarity	NPC206003
0.5437	Remote Similarity	NPC473610
0.5385	Remote Similarity	NPC19400
0.5351	Remote Similarity	NPC116756
0.5328	Remote Similarity	NPC15918
0.5323	Remote Similarity	NPC305771
0.5323	Remote Similarity	NPC94072
0.5323	Remote Similarity	NPC169816
0.5315	Remote Similarity	NPC51172
0.5315	Remote Similarity	NPC49032
0.5234	Remote Similarity	NPC6295
0.5231	Remote Similarity	NPC329807
0.5169	Remote Similarity	NPC92297
0.5167	Remote Similarity	NPC470866
0.5152	Remote Similarity	NPC481418
0.5149	Remote Similarity	NPC485594
0.5135	Remote Similarity	NPC475643
0.5088	Remote Similarity	NPC184617
0.5075	Remote Similarity	NPC329727
0.5045	Remote Similarity	NPC473601
0.5044	Remote Similarity	NPC249553
0.5044	Remote Similarity	NPC182900

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC215408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7387
0.1-0.2	1701
0.2-0.3	55
0.3-0.4	3
0.4-0.5	2
0.5-0.6	2
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
0.5816	Remote Similarity	NPD8171	Phase 2
0.5524	Remote Similarity	NPD8170	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