NPASS Compound

Natural Product: NPC292465

Natural Product ID	NPC292465
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KIAIAZNJHWWAFM-LZUXFAODSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21630154
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 93 99 0 0 0 0 0 0 0 0999 V2000 9.0876 -0.3772 -1.5352 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8787 -0.0682 -0.6572 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2744 1.2250 -1.0970 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8596 1.4112 -0.5868 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0815 0.0927 -0.6838 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7115 0.3063 -1.2922 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7455 -0.0827 -2.7338 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8535 -0.6821 -0.5176 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6237 -0.7690 0.7778 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8005 0.1810 1.6680 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4531 -0.3050 1.3069 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2656 0.4153 1.8005 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3005 0.5719 3.2746 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8579 0.0247 3.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0632 -0.2019 3.4163 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1336 -0.7592 4.2587 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4478 -0.9726 3.6038 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5274 0.0271 2.4730 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4440 -0.3530 1.4196 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1513 0.1459 1.9761 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1435 1.6572 1.7727 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9156 -0.4723 1.3676 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9584 -0.6524 -0.1044 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3697 -1.0252 -0.7111 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4780 -0.1698 -0.2154 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2583 1.2376 -0.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9072 0.2616 0.2798 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3204 -0.5425 -0.7433 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8302 -0.5103 -0.9514 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0602 -0.9790 -2.3758 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5606 0.1586 -3.2644 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1535 0.4645 -2.8284 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0230 1.9202 -2.4115 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6342 -0.4083 -1.9157 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3614 1.2651 -2.9830 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3871 -1.2831 -2.6179 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4899 -1.4192 -0.1254 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4851 -0.7388 4.4860 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8970 -0.3733 0.5876 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7993 -0.8444 -1.4151 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9092 -1.2050 -0.6567 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7695 -1.0595 -0.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8258 -0.9045 -2.4522 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6683 0.5518 -1.7008 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2968 0.0026 0.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8864 2.0462 -0.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3594 1.4048 -2.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3941 2.2105 -1.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9377 1.7459 0.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4546 1.3558 -1.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3956 -0.9951 -2.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2014 0.6815 -3.3727 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7401 -0.3975 -3.0622 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8524 -1.6435 -1.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5186 -1.7811 1.2498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0817 0.0416 2.7259 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0455 1.1988 1.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3974 -1.3877 1.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2075 1.4277 1.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5201 1.6340 3.5741 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2020 0.0134 3.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7664 -0.2237 5.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3063 -0.0707 5.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8121 -1.7762 4.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5115 -1.9905 3.1407 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5173 0.1130 2.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2650 1.0042 2.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3941 -1.4606 1.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6274 2.1229 2.6287 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1581 2.0895 1.6757 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 1.9036 0.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7565 -1.4577 1.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6439 -1.4903 -0.3371 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3923 0.2538 -0.5738 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5998 -2.0750 -0.4838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2282 -0.9742 -1.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5447 1.2427 -1.7743 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7996 1.9997 -0.1011 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2022 1.5036 -0.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1509 -1.6072 -0.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2398 0.5075 -0.8761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4056 -1.8586 -2.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6528 -0.0952 -4.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5179 0.3725 -3.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2363 2.5198 -3.3276 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9765 2.1110 -2.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7461 2.2218 -1.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3316 1.0364 -3.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5777 -2.2542 -2.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1718 -2.3227 -0.3406 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0731 -0.0506 4.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5569 -1.4945 0.3538 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4113 -2.1172 -1.0816 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 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 19 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 32 34 1 0 31 35 1 0 30 36 1 0 29 37 1 0 17 38 1 0 9 39 1 0 5 40 1 6 40 41 1 0 41 2 1 0 39 5 1 0 25 8 1 0 34 28 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 1 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 6 50 1 6 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 6 9 55 1 1 10 56 1 0 10 57 1 0 11 58 1 6 12 59 1 6 13 60 1 0 13 61 1 0 14 62 1 0 16 63 1 0 16 64 1 0 17 65 1 6 18 66 1 0 18 67 1 0 19 68 1 6 21 69 1 0 21 70 1 0 21 71 1 0 22 72 1 1 23 73 1 0 23 74 1 0 24 75 1 0 24 76 1 0 26 77 1 0 26 78 1 0 26 79 1 0 28 80 1 1 29 81 1 6 30 82 1 6 31 83 1 6 32 84 1 6 33 85 1 0 33 86 1 0 33 87 1 0 35 88 1 0 36 89 1 0 37 90 1 0 38 91 1 0 41 92 1 0 41 93 1 0 M END

Standard InCHIKey	KIAIAZNJHWWAFM-LZUXFAODSA-N
Standard InCHI	InChI=1S/C33H52O8/c1-16-8-11-33(38-15-16)17(2)26-24(41-33)14-23-21-7-6-19-12-20(34)13-25(32(19,5)22(21)9-10-31(23,26)4)40-30-29(37)28(36)27(35)18(3)39-30/h6,16-18,20-30,34-37H,7-15H2,1-5H3/t16-,17-,18+,20+,21+,22-,23-,24-,25+,26-,27-,28-,29+,30-,31-,32-,33+/m0/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](C[C@H]([C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@H]([C@@H](C)O3)O)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.37	Volume:	587.114 ? Van der Waals volume.
Dense:	0.982	LogP:	4.215 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.15 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.649 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	36.0
TPSA:	117.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.369	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.91	Fsp³:	0.939
MCE-18:	171.562 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.768	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? 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:	0.177	Promiscuous compounds:	0.016

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.528	MDCK Permeability:	-5.044
Pgp-inhibitor:	0.005	Pgp-substrate:	0.962
PAMPA:	0.97 ? 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%):	0.275	30% Bioavailability (F30%):	0.815
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.221
Plasma Protein Binding (PPB):	62.418%	Volume Distribution (VD):	-0.293
Fu:	34.613% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.961
BSEP inhibitor:	0.313

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.966	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.985
HLM stability:	0.1 ? 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):

6.574

Half-life (T1/2):

2.0

ADMET: Toxicity

hERG Blockers:	0.078	hERG Blockers (10um):	0.248
Human Hepatotoxicity (H-HT):	0.618	Drug-induced Liver Injury (DILI):	0.791
AMES Toxicity:	0.53	Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.811	Skin Sensitization:	0.999
Carcinogencity:	0.651	Eye Corrosion:	0.0
Eye Irritation:	0.058	Respiratory Toxicity:	0.105
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.93
Hematotoxicity:	0.161	Drug-induced Nephrotoxicity:	0.64
Genotoxicity:	0.022	RPMI-8226 Immunitoxicity:	0.226
A549 Cytotoxicity:	0.681	Hek293 Cytotoxicity:	0.822
BCF:	1.985 ? 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:	3.617 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.73 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.281 ? 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
NPO1287	Coriaria nepalensis	Species	Coriariaceae	Eukaryota	n.a.	root	n.a.	PMID[12016873]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	roots	n.a.	n.a.	PMID[19729316]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9588	Atelopus chiriquiensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22493	Xenia crassa	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25200	Takifugu niphobles	Species	Tetraodontidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22493	Xenia crassa	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9474	Clausena pentaphylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25200	Takifugu niphobles	Species	Tetraodontidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1287	Coriaria nepalensis	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9588	Atelopus chiriquiensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5848	Pimpinella nudicaulis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5594	Notholaena nivea	Species	Pteridaceae	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 NPC292465 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	22309
0.1-0.2	24103
0.2-0.3	2945
0.3-0.4	281
0.4-0.5	103
0.5-0.6	70
0.6-0.7	35
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8875	High Similarity	NPC306131
0.8875	High Similarity	NPC200802
0.8452	Intermediate Similarity	NPC70204
0.7717	Intermediate Similarity	NPC294129
0.7416	Intermediate Similarity	NPC475670
0.7253	Intermediate Similarity	NPC112274
0.7195	Intermediate Similarity	NPC473774
0.7195	Intermediate Similarity	NPC481419
0.7195	Intermediate Similarity	NPC481417
0.6977	Remote Similarity	NPC13190
0.6962	Remote Similarity	NPC473923
0.6804	Remote Similarity	NPC475247
0.679	Remote Similarity	NPC473476
0.6588	Remote Similarity	NPC481420
0.6588	Remote Similarity	NPC481421
0.6582	Remote Similarity	NPC235126
0.6582	Remote Similarity	NPC242419
0.6559	Remote Similarity	NPC470432
0.6559	Remote Similarity	NPC230507
0.6477	Remote Similarity	NPC181845
0.6429	Remote Similarity	NPC144790
0.6429	Remote Similarity	NPC149400
0.6421	Remote Similarity	NPC113044
0.6421	Remote Similarity	NPC283829
0.6421	Remote Similarity	NPC14704
0.6421	Remote Similarity	NPC161676
0.6413	Remote Similarity	NPC476538
0.6413	Remote Similarity	NPC476539
0.6354	Remote Similarity	NPC51154
0.6322	Remote Similarity	NPC24960
0.6304	Remote Similarity	NPC476540
0.6304	Remote Similarity	NPC476541
0.6296	Remote Similarity	NPC177818
0.6292	Remote Similarity	NPC481424
0.6292	Remote Similarity	NPC481422
0.6289	Remote Similarity	NPC11548
0.6224	Remote Similarity	NPC470433
0.6224	Remote Similarity	NPC46190
0.6224	Remote Similarity	NPC171073
0.6224	Remote Similarity	NPC602423
0.61	Remote Similarity	NPC300557
0.604	Remote Similarity	NPC480555
0.604	Remote Similarity	NPC150372
0.6	Remote Similarity	NPC485594
0.5914	Remote Similarity	NPC477451
0.5865	Remote Similarity	NPC269297
0.5865	Remote Similarity	NPC222202
0.5843	Remote Similarity	NPC481418
0.5833	Remote Similarity	NPC486119
0.581	Remote Similarity	NPC475333
0.581	Remote Similarity	NPC32361
0.581	Remote Similarity	NPC224098
0.581	Remote Similarity	NPC208383
0.5806	Remote Similarity	NPC131693
0.5806	Remote Similarity	NPC475436
0.5794	Remote Similarity	NPC229962
0.5761	Remote Similarity	NPC481425
0.5761	Remote Similarity	NPC481426
0.5729	Remote Similarity	NPC19400
0.5701	Remote Similarity	NPC480554
0.5686	Remote Similarity	NPC248746
0.5684	Remote Similarity	NPC222731
0.5648	Remote Similarity	NPC195560
0.5631	Remote Similarity	NPC6806
0.5618	Remote Similarity	NPC277715
0.5596	Remote Similarity	NPC480553
0.5591	Remote Similarity	NPC226642
0.5567	Remote Similarity	NPC475431
0.5556	Remote Similarity	NPC6295
0.5534	Remote Similarity	NPC477809
0.5532	Remote Similarity	NPC297348
0.5532	Remote Similarity	NPC325828
0.5532	Remote Similarity	NPC249204
0.5532	Remote Similarity	NPC48339
0.5532	Remote Similarity	NPC177834
0.5532	Remote Similarity	NPC141769
0.5532	Remote Similarity	NPC477547
0.55	Remote Similarity	NPC141433
0.5474	Remote Similarity	NPC234352
0.5439	Remote Similarity	NPC198325
0.54	Remote Similarity	NPC485595
0.537	Remote Similarity	NPC309278
0.5361	Remote Similarity	NPC473616
0.5351	Remote Similarity	NPC480556
0.5347	Remote Similarity	NPC195297
0.5345	Remote Similarity	NPC207243
0.5333	Remote Similarity	NPC42171
0.5321	Remote Similarity	NPC194207
0.5321	Remote Similarity	NPC22779
0.5312	Remote Similarity	NPC294686
0.5309	Remote Similarity	NPC248944
0.5309	Remote Similarity	NPC7479
0.5309	Remote Similarity	NPC257296
0.5306	Remote Similarity	NPC206003
0.5306	Remote Similarity	NPC473610
0.5304	Remote Similarity	NPC224314
0.5299	Remote Similarity	NPC233391
0.5288	Remote Similarity	NPC475403
0.5253	Remote Similarity	NPC211354
0.5253	Remote Similarity	NPC107188
0.5227	Remote Similarity	NPC176406
0.5204	Remote Similarity	NPC250393
0.5172	Remote Similarity	NPC477807
0.5165	Remote Similarity	NPC88962
0.5149	Remote Similarity	NPC107962
0.514	Remote Similarity	NPC160888
0.5114	Remote Similarity	NPC100451
0.5104	Remote Similarity	NPC481423
0.5091	Remote Similarity	NPC475487
0.5088	Remote Similarity	NPC232054
0.506	Remote Similarity	NPC296734
0.5055	Remote Similarity	NPC473469
0.5046	Remote Similarity	NPC148965
0.5044	Remote Similarity	NPC477811

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC292465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7441
0.1-0.2	1622
0.2-0.3	72
0.3-0.4	11
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
0.5532	Remote Similarity	NPD8171	Phase 2
0.5309	Remote Similarity	NPD6928	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