NPASS Compound

Structure

NPC66356 OpenBabel06302215422D 78 86 0 0 1 0 0 0 0 0999 V2000 11.0524 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1190 -3.6347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4357 -4.3180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5024 -4.0679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2523 -3.1345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9355 -2.4512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8689 -2.7013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6854 -1.5179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3687 -0.8346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3021 -1.0847 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9854 -0.4014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7353 0.5320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.4185 1.2152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3519 0.9651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0352 1.6484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.9685 1.3983 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 14.6518 2.0816 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.4017 3.0149 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.4683 3.2650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7851 2.5818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.0850 3.6982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.0183 3.4481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.7016 4.1314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.2684 2.5148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5852 1.8315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2186 0.4649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8019 0.7820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1186 0.0988 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1853 0.3489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6851 2.2156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8183 2.7158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3683 2.8989 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2052 3.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2052 4.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3683 4.8315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8852 5.6683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8515 5.6683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5315 4.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5315 3.3820 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6947 2.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8578 3.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0210 2.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0210 1.9326 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1842 1.4494 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1842 2.4157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3473 1.9326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5105 1.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5105 0.4831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3473 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8305 -0.8368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8642 -0.8368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8979 -0.8368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1842 0.4831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0210 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8578 0.4831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8578 1.4494 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5315 0.4831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6947 1.9326 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6947 0.9663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5315 1.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3683 1.9326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6737 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8368 0.4831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8368 1.4494 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9326 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8368 1.4494 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8368 0.4831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6737 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5105 0.4831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6737 1.9326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.8989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6737 1.9326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9187 -0.6515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5522 -2.0181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3189 -2.8844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8191 -4.7511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6858 -5.2513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 4 1 0 0 0 0 3 78 1 6 0 0 0 4 5 1 0 0 0 0 4 77 1 1 0 0 0 5 6 1 0 0 0 0 5 76 1 1 0 0 0 6 7 1 0 0 0 0 6 8 1 6 0 0 0 9 8 1 1 0 0 0 9 10 1 0 0 0 0 9 28 1 0 0 0 0 10 11 1 0 0 0 0 10 75 1 6 0 0 0 11 12 1 0 0 0 0 11 74 1 1 0 0 0 12 13 1 6 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 15 14 1 6 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 21 1 1 0 0 0 19 20 1 0 0 0 0 21 22 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 27 28 1 0 0 0 0 28 29 1 6 0 0 0 29 30 1 0 0 0 0 30 31 2 0 0 0 0 32 30 1 1 0 0 0 32 61 1 0 0 0 0 32 33 1 0 0 0 0 32 39 1 0 0 0 0 33 34 1 0 0 0 0 34 35 1 0 0 0 0 35 36 1 0 0 0 0 35 37 1 0 0 0 0 35 38 1 0 0 0 0 39 38 1 6 0 0 0 39 40 1 0 0 0 0 40 58 1 0 0 0 0 40 41 2 0 0 0 0 41 42 1 0 0 0 0 43 42 1 1 0 0 0 43 44 1 0 0 0 0 43 56 1 0 0 0 0 44 53 1 0 0 0 0 44 45 1 1 0 0 0 44 46 1 0 0 0 0 46 47 1 0 0 0 0 47 48 1 0 0 0 0 48 49 1 0 0 0 0 48 62 1 1 0 0 0 49 50 1 1 0 0 0 49 51 1 0 0 0 0 49 53 1 0 0 0 0 51 52 1 0 0 0 0 53 54 1 1 0 0 0 54 55 1 0 0 0 0 55 56 1 0 0 0 0 56 57 1 1 0 0 0 56 58 1 0 0 0 0 58 59 1 6 0 0 0 58 60 1 0 0 0 0 60 61 1 0 0 0 0 63 62 1 6 0 0 0 63 64 1 0 0 0 0 63 70 1 0 0 0 0 64 65 1 0 0 0 0 64 73 1 1 0 0 0 65 66 1 0 0 0 0 65 72 1 6 0 0 0 66 67 1 0 0 0 0 66 71 1 1 0 0 0 67 68 1 6 0 0 0 67 70 1 0 0 0 0 68 69 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	326.404
LogP:	4.85
LogD:	3.678
LogS:	-3.912
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	5.585
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.01
MDCK Permeability:	9.073396540770773e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.779
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	86.11798858642578%
Volume Distribution (VD):	0.88
Pgp-substrate:	7.857698917388916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.413
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.843
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.286
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	14.979
Half-life (T1/2):	0.148

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.577
Drug-inuced Liver Injury (DILI):	0.125
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.646
Carcinogencity:	0.776
Eye Corrosion:	0.032
Eye Irritation:	0.09
Respiratory Toxicity:	0.901

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC66356

Natural Product ID:	NPC66356
*Common Name:**	FIKNNHYPIMPJBP-GQYWHWDKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FIKNNHYPIMPJBP-GQYWHWDKSA-N
Standard InCHI:	InChI=1S/C55H88O23/c1-24-34(59)38(63)42(67)46(72-24)77-44-40(65)36(61)30(22-71-45-41(66)37(62)29(21-70-45)73-25(2)58)75-48(44)78-49(69)55-17-15-50(3,4)19-27(55)26-9-10-32-51(5)13-12-33(76-47-43(68)39(64)35(60)28(20-56)74-47)52(6,23-57)31(51)11-14-54(32,8)53(26,7)16-18-55/h9,24,27-48,56-57,59-68H,10-23H2,1-8H3/t24-,27-,28+,29+,30+,31+,32+,33-,34-,35+,36+,37-,38+,39-,40-,41+,42+,43+,44+,45-,46-,47-,48-,51-,52-,53+,54+,55-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)OC(=O)C)O)O)O[C@H]1OC(=O)[C@@]12CCC(C)(C)C[C@H]2C2=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]2(C)CC1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	72945099
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11735581]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5155	Peritassa compta	Species	Celastraceae	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	NP ID	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC66356 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	1737
0.2-0.3	5108
0.3-0.4	11934
0.4-0.5	10269
0.5-0.6	6164
0.6-0.7	3984
0.7-0.8	1930
0.8-0.85	607
0.85-0.9	291
0.9-0.95	169
0.95-1	243

Similarity Score	Similarity Level	Natural Product ID

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66356 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	2042
0.2-0.3	3876
0.3-0.4	1952
0.4-0.5	598
0.5-0.6	266
0.6-0.7	142
0.7-0.8	21
0.8-0.85	8
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

Bioactivity similarity: Similar Natural Products in NPASS

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