NPASS Compound

Structure

CID43300 OpenBabel06191715372D 31 35 0 0 1 0 0 0 0 0999 V2000 5.7003 0.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1706 0.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4389 1.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9480 0.5688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4598 -2.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0242 1.9073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8680 -1.4481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6391 0.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8193 1.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0977 -1.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6382 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6396 2.8380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2793 -1.8914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8201 2.3655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8190 -0.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6399 -1.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8201 -1.4189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7661 0.1970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0975 -0.4721 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6394 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6385 0.9460 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9465 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4586 2.3645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4592 -0.4725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4580 1.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4595 -1.4184 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8195 1.4195 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8198 -0.4730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3083 2.8545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 2 0 0 0 0 25 27 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.37
Volume:	488.171
LogP:	6.496
LogD:	6.014
LogS:	-6.382
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	4.643
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.24
MDCK Permeability:	1.9369883375475183e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.334
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	93.61042022705078%
Volume Distribution (VD):	1.233
Pgp-substrate:	1.7330877780914307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.734
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.976
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.434
CYP3A4-substrate:	0.466

ADMET: Excretion

Clearance (CL):	4.198
Half-life (T1/2):	0.232

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.727
Skin Sensitization:	0.214
Carcinogencity:	0.004
Eye Corrosion:	0.976
Eye Irritation:	0.927
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC43300

Natural Product ID:	NPC43300
*Common Name:**	Lupenone
IUPAC Name:	(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms:	Lupenone; Lupeone
Standard InCHIKey:	GRBHNQFQFHLCHO-BHMAJAPKSA-N
Standard InCHI:	InChI=1S/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1
SMILES:	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486393
PubChem CID:	92158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO809	Leitneria floridana	Species	Simaroubaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11141127]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713421]
NPO7294	Cunninghamella echinulata	Species	Cunninghamellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12740180]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[14510598]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[14738378]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15595606]
NPO17857	Leptogorgia alba	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844963]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124753]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562827]
NPO24639	Streptomyces filamentosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17284073]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	roots	Phitsanulok Province, Thailand	2004-MAY	PMID[17480099]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17480099]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20509707]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO19556	Clathrina clathrus	Species	Clathrinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590100]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20939540]
NPO4756	Mesua elegans	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20943395]
NPO31410	Cupania cinerea	Species	Sapindaceae	Eukaryota	n.a.	bark	n.a.	PMID[21438586]
NPO10224	Operculina turpethum	Species	Convolvulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21866900]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22817615]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO546	Candida albicans	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23902158]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964677]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195447]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark	Urubamba, Cusco, Peru	n.a.	PMID[25927586]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	Gum resin	n.a.	n.a.	PMID[26457560]
NPO40286	Phoradendron vernicosum	Species	Viscaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29120172]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO5710	Michelia rajaniana	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3236012]
NPO20288	Polytolypa hystricis	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691217]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22978	Morus tinctoria	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19139	Senecio polyodon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20453	Cayratia japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13459	Nitraria tangutorum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15736	Liatris spicata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1792	Terminalia calamansanay	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20453	Cayratia japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22978	Morus tinctoria	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19139	Senecio polyodon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22294	Pteris inaequalis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13459	Nitraria tangutorum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO878	Hannoa undulata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15736	Liatris spicata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23706	Breea segeta	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26656	Heliotropium hirsutissimum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11127	Inulanthera calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6557	Lotus villosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12097	Prumnopitys ferruginea	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4757	Pinus montezumae	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21368	Tricholoma batschii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16555	Acanthoscelides obtectus	Species	Chrysomelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3215	Phora atra	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9318	Stevia serrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22871	Aster alpinus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29440	Sarcomyxa serotina	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO809	Leitneria floridana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7856	Streptomyces halstedii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15736	Liatris spicata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15875	Scolopia chinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO546	Candida albicans	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1490	Goldfussia yunnanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10224	Operculina turpethum	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12482	Strobilomyces floccopus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10009	Oxylobus arbutifolius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2076	Coffea bengalensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5515	Cephalocroton cordofanus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22711	Athanasia dregeana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21822	Berberis crataegina	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11244	Chrysolaena propinqua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9881	Petrosia hebes	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17136	Centaurea coronopifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21951	Paramignya griffithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9830	Arum maximum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2480	Amoora rohituka	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2633	Baccharis minutiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8198	Podocarpus montanus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5348	Colletotrichum acutatum	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20592	Rhodoglossum japonicum	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4442	Artemisia austriaca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12990	Umbelopsis vinacea	Species	Umbelopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25530	Daphne blagayana	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3357	Alnus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7011	Chamomilla recutita	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO924	Russula subnigricans	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4756	Mesua elegans	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17674	Bishopanthus soliceps	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28383	Vernonia tufnellae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21530	Arnica viscosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19556	Clathrina clathrus	Species	Clathrinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22650	Helenium quadridentatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22978	Morus tinctoria	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22927	Xanthoparmelia pokornyi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3651	Ajania achilleoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21101	Felicia amelloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6338	Chilo auricilius	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28627.1	Coptis trifolia subsp. groenlandica	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19139	Senecio polyodon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13751	Eupatorium leptophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO81	Erythrina orientalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8807	Laurentia longiflora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9944	Salisaeta longa	Species	Rhodothermaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8378	Fagara heitzii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22766	Lophanthus chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22599	Crataegus pontica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18684	Calophyllum thwaitesii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22647	Araucaria araucana	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1296	Tichocarpus crinitus	Species	Tichocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9750	Dysoxylum malabaricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23353	[polyangium] brachysporum	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13489	Mahonia nepalensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4372	Halimium halimifolium	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23952	Phlomoides medicinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9469	Digitalis obscura	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9045	Aegiceras majus	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1572.1	Artemisia dracunculus var. glauca	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22529	Calceolaria thyrsiflora	Species	Calceolariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24639	Streptomyces filamentosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25475	Syphonota geographica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4628	Aloe deltoideodonta	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5060	Onychopetalum amazonicum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7294	Cunninghamella echinulata	Species	Cunninghamellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4061	Trollius europaeus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2455	Thermopsis mollis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9714	Symphyopappus compressus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21582	Manihot esculenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13374	Primula grandiflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4382	Elmerrillia papuana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20453	Cayratia japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1792	Terminalia calamansanay	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO878	Hannoa undulata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6828	Purpura aperta	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12152	Nicotiana raimondii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26652	Soroseris hookeriana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11064	Haemanthus toxicarius	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4668	Sideritis flavovirens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20801	Antrodia sinuosa	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28078	Melaleuca decora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20015	Echinocystis lobata	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9608	Lepraria citrina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5710	Michelia rajaniana	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20288	Polytolypa hystricis	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17857	Leptogorgia alba	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22812	Acacia cambagei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16711	Baccharis solieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13459	Nitraria tangutorum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1288	Phora scalaris	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7674	Tragopogon orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8977	0tholaena aschenborniana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10661	Senecio fulgens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12571	Monanthotaxis congoensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22294	Pteris inaequalis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23025	Roccellaria mollis	Species	Roccellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7127	Artemisia alba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22090	Aframomum alboviolaceum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23989	Cyclamen neapolitanum	Species	Primulaceae	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

Activity Type	# Activity
EC50	3
ED50	1
IC50	20
Others	15

Activity Type	# Activity
Cell Line	27
Individual Protein	6
NON-MOLECULAR	2
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	>	10.0	ug ml-1	PMID[466052]
NPT319	Cell Line	B16	Mus musculus	ED50	=	0.35	uM	PMID[466054]
NPT319	Cell Line	B16	Mus musculus	IC50	=	25400.0	nM	PMID[466054]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[466055]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[466055]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	10.0	ug.mL-1	PMID[466055]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	0.0	nM	PMID[466056]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	400.0	nM	PMID[466057]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90000.0	nM	PMID[466058]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	2.1	ug.mL-1	PMID[466059]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	38500.0	nM	PMID[466062]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	89.6	%	PMID[466062]
NPT2245	Cell Line	SiHa	Homo sapiens	CC50	>	500000.0	nM	PMID[466064]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	>	500000.0	nM	PMID[466064]
NPT83	Cell Line	MCF7	Homo sapiens	CC50	>	500000.0	nM	PMID[466064]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	CC50	>	500000.0	nM	PMID[466064]
NPT90	Cell Line	DU-145	Homo sapiens	CC50	>	500000.0	nM	PMID[466064]
NPT91	Cell Line	KB	Homo sapiens	CC50	>	500000.0	nM	PMID[466064]
NPT1171	Cell Line	HEp-2	Homo sapiens	CC50	>	500000.0	nM	PMID[466064]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	500000.0	nM	PMID[466064]
NPT71	Cell Line	HEK293	Homo sapiens	CC50	>	500000.0	nM	PMID[466064]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	500000.0	nM	PMID[466064]
NPT2245	Cell Line	SiHa	Homo sapiens	IC50	>	500000.0	nM	PMID[466064]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	500000.0	nM	PMID[466064]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	500000.0	nM	PMID[466064]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	500000.0	nM	PMID[466064]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	500000.0	nM	PMID[466064]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	500000.0	nM	PMID[466064]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	500000.0	nM	PMID[466064]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	500000.0	nM	PMID[466064]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	-2.4	%	PMID[466053]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	>	10000.0	nM	PMID[466056]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Efficacy	=	0.0	%	PMID[466056]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	4700.0	nM	PMID[466058]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	>	90000.0	nM	PMID[466058]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	77000.0	nM	PMID[466061]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	38800.0	nM	PMID[466062]
NPT27	Others	Unspecified		Activity	=	87.72	%	PMID[466062]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[466063]

☑ 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 NPC43300 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	199
0.1-0.2	3660
0.2-0.3	18741
0.3-0.4	8079
0.4-0.5	5944
0.5-0.6	4429
0.6-0.7	1412
0.7-0.8	188
0.8-0.85	35
0.85-0.9	8
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9365	High Similarity	NPC107704
0.9365	High Similarity	NPC96812
0.9365	High Similarity	NPC168824
0.9365	High Similarity	NPC39462
0.9365	High Similarity	NPC189917
0.8971	High Similarity	NPC159497
0.8939	High Similarity	NPC477857
0.8806	High Similarity	NPC214770
0.8806	High Similarity	NPC477856
0.8788	High Similarity	NPC20610
0.8657	High Similarity	NPC182815
0.8571	High Similarity	NPC293803
0.8529	High Similarity	NPC159577
0.8529	High Similarity	NPC35734
0.8529	High Similarity	NPC40574
0.8529	High Similarity	NPC282593
0.8507	High Similarity	NPC296697
0.8507	High Similarity	NPC39157
0.8507	High Similarity	NPC142754
0.8507	High Similarity	NPC82477
0.8472	Intermediate Similarity	NPC63020
0.8406	Intermediate Similarity	NPC470078
0.8406	Intermediate Similarity	NPC115023
0.8382	Intermediate Similarity	NPC286814
0.8361	Intermediate Similarity	NPC184819
0.8358	Intermediate Similarity	NPC220210
0.8358	Intermediate Similarity	NPC20181
0.8356	Intermediate Similarity	NPC192744
0.8356	Intermediate Similarity	NPC201459
0.8286	Intermediate Similarity	NPC474228
0.8286	Intermediate Similarity	NPC251705
0.8286	Intermediate Similarity	NPC303613
0.8261	Intermediate Similarity	NPC307176
0.8226	Intermediate Similarity	NPC151464
0.8226	Intermediate Similarity	NPC143597
0.8209	Intermediate Similarity	NPC323005
0.8143	Intermediate Similarity	NPC190035
0.8143	Intermediate Similarity	NPC234707
0.8133	Intermediate Similarity	NPC474484
0.8133	Intermediate Similarity	NPC103754
0.8116	Intermediate Similarity	NPC139397
0.8082	Intermediate Similarity	NPC68828
0.8082	Intermediate Similarity	NPC91665
0.8056	Intermediate Similarity	NPC255650
0.8033	Intermediate Similarity	NPC127944
0.8028	Intermediate Similarity	NPC474488
0.8028	Intermediate Similarity	NPC470045
0.8028	Intermediate Similarity	NPC470044
0.8	Intermediate Similarity	NPC270042
0.8	Intermediate Similarity	NPC265782
0.8	Intermediate Similarity	NPC251929
0.8	Intermediate Similarity	NPC2634
0.8	Intermediate Similarity	NPC260040
0.8	Intermediate Similarity	NPC474509
0.7945	Intermediate Similarity	NPC69408
0.7937	Intermediate Similarity	NPC474105
0.7922	Intermediate Similarity	NPC472740
0.7922	Intermediate Similarity	NPC475726
0.7922	Intermediate Similarity	NPC472743
0.7922	Intermediate Similarity	NPC175410
0.7917	Intermediate Similarity	NPC255021
0.7917	Intermediate Similarity	NPC309852
0.791	Intermediate Similarity	NPC469662
0.7903	Intermediate Similarity	NPC288296
0.7903	Intermediate Similarity	NPC53245
0.7887	Intermediate Similarity	NPC54123
0.7887	Intermediate Similarity	NPC305501
0.7887	Intermediate Similarity	NPC225467
0.7867	Intermediate Similarity	NPC215843
0.7838	Intermediate Similarity	NPC66105
0.7838	Intermediate Similarity	NPC470557
0.7821	Intermediate Similarity	NPC474233
0.7821	Intermediate Similarity	NPC475745
0.7821	Intermediate Similarity	NPC474482
0.7778	Intermediate Similarity	NPC307063
0.7778	Intermediate Similarity	NPC279241
0.7778	Intermediate Similarity	NPC200258
0.7778	Intermediate Similarity	NPC52667
0.7761	Intermediate Similarity	NPC202118
0.7761	Intermediate Similarity	NPC197238
0.7733	Intermediate Similarity	NPC82635
0.7733	Intermediate Similarity	NPC470052
0.7722	Intermediate Similarity	NPC292553
0.7722	Intermediate Similarity	NPC201655
0.7705	Intermediate Similarity	NPC236623
0.7703	Intermediate Similarity	NPC246445
0.7671	Intermediate Similarity	NPC474797
0.7671	Intermediate Similarity	NPC474796
0.7671	Intermediate Similarity	NPC329866
0.7639	Intermediate Similarity	NPC223187
0.7632	Intermediate Similarity	NPC471475
0.7625	Intermediate Similarity	NPC472738
0.7612	Intermediate Similarity	NPC60565
0.76	Intermediate Similarity	NPC106078
0.76	Intermediate Similarity	NPC212661
0.76	Intermediate Similarity	NPC471035
0.7595	Intermediate Similarity	NPC264665
0.7595	Intermediate Similarity	NPC74595
0.7595	Intermediate Similarity	NPC475509
0.7571	Intermediate Similarity	NPC176107
0.7568	Intermediate Similarity	NPC473171
0.7564	Intermediate Similarity	NPC477858
0.7564	Intermediate Similarity	NPC145143
0.7538	Intermediate Similarity	NPC49575
0.7538	Intermediate Similarity	NPC55004
0.7538	Intermediate Similarity	NPC230823
0.7538	Intermediate Similarity	NPC267626
0.7534	Intermediate Similarity	NPC244708
0.7534	Intermediate Similarity	NPC330659
0.7534	Intermediate Similarity	NPC36310
0.7534	Intermediate Similarity	NPC161187
0.7531	Intermediate Similarity	NPC57469
0.7531	Intermediate Similarity	NPC4643
0.75	Intermediate Similarity	NPC264317
0.75	Intermediate Similarity	NPC469996
0.75	Intermediate Similarity	NPC294438
0.75	Intermediate Similarity	NPC98270
0.75	Intermediate Similarity	NPC472306
0.7467	Intermediate Similarity	NPC20466
0.7465	Intermediate Similarity	NPC473225
0.7439	Intermediate Similarity	NPC472739
0.7439	Intermediate Similarity	NPC474719
0.7436	Intermediate Similarity	NPC147066
0.7429	Intermediate Similarity	NPC92327
0.7424	Intermediate Similarity	NPC127798
0.7407	Intermediate Similarity	NPC2783
0.7407	Intermediate Similarity	NPC98236
0.7407	Intermediate Similarity	NPC269396
0.7407	Intermediate Similarity	NPC12774
0.7403	Intermediate Similarity	NPC90965
0.7403	Intermediate Similarity	NPC170793
0.7375	Intermediate Similarity	NPC181743
0.7375	Intermediate Similarity	NPC16287
0.7375	Intermediate Similarity	NPC178025
0.7353	Intermediate Similarity	NPC213152
0.7342	Intermediate Similarity	NPC472239
0.7342	Intermediate Similarity	NPC320514
0.7317	Intermediate Similarity	NPC269360
0.7317	Intermediate Similarity	NPC264005
0.7317	Intermediate Similarity	NPC33768
0.7317	Intermediate Similarity	NPC93778
0.7308	Intermediate Similarity	NPC164999
0.7308	Intermediate Similarity	NPC267517
0.7284	Intermediate Similarity	NPC76518
0.7284	Intermediate Similarity	NPC60350
0.7284	Intermediate Similarity	NPC137493
0.7273	Intermediate Similarity	NPC321690
0.7273	Intermediate Similarity	NPC115515
0.726	Intermediate Similarity	NPC108131
0.725	Intermediate Similarity	NPC470047
0.725	Intermediate Similarity	NPC470046
0.725	Intermediate Similarity	NPC21667
0.725	Intermediate Similarity	NPC245866
0.7246	Intermediate Similarity	NPC165695
0.7237	Intermediate Similarity	NPC469796
0.7237	Intermediate Similarity	NPC469793
0.7229	Intermediate Similarity	NPC4309
0.7229	Intermediate Similarity	NPC16377
0.7229	Intermediate Similarity	NPC471900
0.7222	Intermediate Similarity	NPC260474
0.7222	Intermediate Similarity	NPC188292
0.7222	Intermediate Similarity	NPC310992
0.7215	Intermediate Similarity	NPC201912
0.7215	Intermediate Similarity	NPC263272
0.7215	Intermediate Similarity	NPC38350
0.7215	Intermediate Similarity	NPC267691
0.7215	Intermediate Similarity	NPC162632
0.7215	Intermediate Similarity	NPC274050
0.7215	Intermediate Similarity	NPC4166
0.7215	Intermediate Similarity	NPC3915
0.7206	Intermediate Similarity	NPC25853
0.7206	Intermediate Similarity	NPC127582
0.72	Intermediate Similarity	NPC255168
0.72	Intermediate Similarity	NPC211641
0.7195	Intermediate Similarity	NPC70661
0.7183	Intermediate Similarity	NPC103734
0.7179	Intermediate Similarity	NPC477371
0.7179	Intermediate Similarity	NPC118987
0.7164	Intermediate Similarity	NPC56905
0.7164	Intermediate Similarity	NPC27610
0.7164	Intermediate Similarity	NPC266295
0.7164	Intermediate Similarity	NPC94991
0.7164	Intermediate Similarity	NPC30215
0.7162	Intermediate Similarity	NPC5701
0.7162	Intermediate Similarity	NPC181204
0.716	Intermediate Similarity	NPC221758
0.716	Intermediate Similarity	NPC85774
0.716	Intermediate Similarity	NPC59453
0.716	Intermediate Similarity	NPC214043
0.716	Intermediate Similarity	NPC82902
0.7143	Intermediate Similarity	NPC274182
0.7143	Intermediate Similarity	NPC247312
0.7143	Intermediate Similarity	NPC220498
0.7143	Intermediate Similarity	NPC475124
0.7143	Intermediate Similarity	NPC213832
0.7143	Intermediate Similarity	NPC271974
0.7143	Intermediate Similarity	NPC285371
0.7143	Intermediate Similarity	NPC212210
0.7143	Intermediate Similarity	NPC57954
0.7125	Intermediate Similarity	NPC310989

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 NPC43300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	3469
0.2-0.3	4108
0.3-0.4	875
0.4-0.5	209
0.5-0.6	172
0.6-0.7	101
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD4747	Approved
0.8235	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD4137	Phase 3
0.8	Intermediate Similarity	NPD4691	Approved
0.7917	Intermediate Similarity	NPD5733	Approved
0.7671	Intermediate Similarity	NPD4058	Approved
0.7671	Intermediate Similarity	NPD4687	Approved
0.7639	Intermediate Similarity	NPD5276	Approved
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4788	Approved
0.716	Intermediate Similarity	NPD4786	Approved
0.7125	Intermediate Similarity	NPD4221	Approved
0.7125	Intermediate Similarity	NPD4223	Phase 3
0.7073	Intermediate Similarity	NPD5329	Approved
0.7024	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6098	Approved
0.6986	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5360	Phase 3
0.6977	Remote Similarity	NPD8035	Phase 2
0.6977	Remote Similarity	NPD8034	Phase 2
0.6951	Remote Similarity	NPD4197	Approved
0.6914	Remote Similarity	NPD3667	Approved
0.6835	Remote Similarity	NPD3617	Approved
0.6824	Remote Similarity	NPD5737	Approved
0.6824	Remote Similarity	NPD6672	Approved
0.68	Remote Similarity	NPD4789	Approved
0.679	Remote Similarity	NPD8028	Phase 2
0.6786	Remote Similarity	NPD4138	Approved
0.6786	Remote Similarity	NPD4693	Phase 3
0.6786	Remote Similarity	NPD4690	Approved
0.6786	Remote Similarity	NPD7521	Approved
0.6786	Remote Similarity	NPD7146	Approved
0.6786	Remote Similarity	NPD5205	Approved
0.6786	Remote Similarity	NPD4688	Approved
0.6786	Remote Similarity	NPD7334	Approved
0.6786	Remote Similarity	NPD4689	Approved
0.6786	Remote Similarity	NPD6684	Approved
0.6786	Remote Similarity	NPD5330	Approved
0.6786	Remote Similarity	NPD6409	Approved
0.6747	Remote Similarity	NPD3665	Phase 1
0.6747	Remote Similarity	NPD3133	Approved
0.6747	Remote Similarity	NPD3668	Phase 3
0.6747	Remote Similarity	NPD3666	Approved
0.6744	Remote Similarity	NPD6080	Approved
0.6744	Remote Similarity	NPD6904	Approved
0.6744	Remote Similarity	NPD5328	Approved
0.6744	Remote Similarity	NPD6673	Approved
0.6712	Remote Similarity	NPD4224	Phase 2
0.6711	Remote Similarity	NPD6081	Approved
0.6711	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5208	Approved
0.6628	Remote Similarity	NPD6903	Approved
0.6627	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6079	Approved
0.6588	Remote Similarity	NPD5690	Phase 2
0.6588	Remote Similarity	NPD3618	Phase 1
0.6588	Remote Similarity	NPD4694	Approved
0.6588	Remote Similarity	NPD5280	Approved
0.6585	Remote Similarity	NPD4692	Approved
0.6585	Remote Similarity	NPD4139	Approved
0.6579	Remote Similarity	NPD4245	Approved
0.6579	Remote Similarity	NPD4244	Approved
0.6575	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4753	Phase 2
0.6517	Remote Similarity	NPD6399	Phase 3
0.6508	Remote Similarity	NPD343	Approved
0.6508	Remote Similarity	NPD345	Approved
0.6508	Remote Similarity	NPD344	Approved
0.6494	Remote Similarity	NPD4758	Discontinued
0.6494	Remote Similarity	NPD4243	Approved
0.6494	Remote Similarity	NPD5777	Approved
0.6447	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3698	Phase 2
0.6429	Remote Similarity	NPD287	Approved
0.6404	Remote Similarity	NPD5693	Phase 1
0.6404	Remote Similarity	NPD6050	Approved
0.6404	Remote Similarity	NPD7515	Phase 2
0.6395	Remote Similarity	NPD5279	Phase 3
0.6395	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4195	Approved
0.6333	Remote Similarity	NPD4202	Approved
0.6329	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4784	Approved
0.6329	Remote Similarity	NPD4785	Approved
0.6292	Remote Similarity	NPD5692	Phase 3
0.6292	Remote Similarity	NPD5207	Approved
0.6265	Remote Similarity	NPD4695	Discontinued
0.6264	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6001	Approved
0.6264	Remote Similarity	NPD7748	Approved
0.6264	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6942	Approved
0.6237	Remote Similarity	NPD6084	Phase 2
0.6237	Remote Similarity	NPD6083	Phase 2
0.6222	Remote Similarity	NPD5281	Approved
0.6222	Remote Similarity	NPD5284	Approved
0.6222	Remote Similarity	NPD5694	Approved
0.622	Remote Similarity	NPD5364	Discontinued
0.6207	Remote Similarity	NPD4519	Discontinued
0.6207	Remote Similarity	NPD4623	Approved
0.6196	Remote Similarity	NPD5210	Approved
0.6196	Remote Similarity	NPD4629	Approved
0.618	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6117	Approved
0.6136	Remote Similarity	NPD3573	Approved
0.6129	Remote Similarity	NPD5221	Approved
0.6129	Remote Similarity	NPD4697	Phase 3
0.6129	Remote Similarity	NPD5222	Approved
0.6129	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4096	Approved
0.6098	Remote Similarity	NPD6116	Phase 1
0.6087	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7525	Registered
0.6064	Remote Similarity	NPD4755	Approved
0.6064	Remote Similarity	NPD7902	Approved
0.6064	Remote Similarity	NPD5173	Approved
0.6049	Remote Similarity	NPD3703	Phase 2
0.6049	Remote Similarity	NPD4190	Phase 3
0.6049	Remote Similarity	NPD5275	Approved
0.6026	Remote Similarity	NPD6922	Approved
0.6026	Remote Similarity	NPD6923	Approved
0.6024	Remote Similarity	NPD6114	Approved
0.6024	Remote Similarity	NPD4776	Phase 2
0.6024	Remote Similarity	NPD6115	Approved
0.6024	Remote Similarity	NPD6697	Approved
0.6024	Remote Similarity	NPD4777	Suspended
0.6024	Remote Similarity	NPD6118	Approved
0.6022	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD5696	Approved
0.5978	Remote Similarity	NPD5133	Approved
0.5949	Remote Similarity	NPD7143	Approved
0.5949	Remote Similarity	NPD6939	Phase 2
0.5949	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD7144	Approved
0.5938	Remote Similarity	NPD5285	Approved
0.5938	Remote Similarity	NPD4700	Approved
0.5938	Remote Similarity	NPD5286	Approved
0.5938	Remote Similarity	NPD4696	Approved
0.5918	Remote Similarity	NPD6052	Approved
0.5889	Remote Similarity	NPD4518	Approved
0.5876	Remote Similarity	NPD5223	Approved
0.5875	Remote Similarity	NPD7152	Approved
0.5875	Remote Similarity	NPD7150	Approved
0.5875	Remote Similarity	NPD7151	Approved
0.5873	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3702	Approved
0.5851	Remote Similarity	NPD5654	Approved
0.5833	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3671	Phase 1
0.5816	Remote Similarity	NPD5224	Approved
0.5816	Remote Similarity	NPD5211	Phase 2
0.5816	Remote Similarity	NPD5225	Approved
0.5816	Remote Similarity	NPD5091	Approved
0.5816	Remote Similarity	NPD5226	Approved
0.5816	Remote Similarity	NPD4633	Approved
0.58	Remote Similarity	NPD6675	Approved
0.58	Remote Similarity	NPD7128	Approved
0.58	Remote Similarity	NPD5739	Approved
0.58	Remote Similarity	NPD6402	Approved
0.5789	Remote Similarity	NPD7732	Phase 3
0.5789	Remote Similarity	NPD7614	Phase 1
0.5783	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD7645	Phase 2
0.5758	Remote Similarity	NPD4754	Approved
0.5758	Remote Similarity	NPD5175	Approved
0.5758	Remote Similarity	NPD5174	Approved
0.5747	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6412	Phase 2
0.5743	Remote Similarity	NPD6614	Approved
0.5732	Remote Similarity	NPD6926	Approved
0.5732	Remote Similarity	NPD6924	Approved
0.5729	Remote Similarity	NPD5959	Approved
0.57	Remote Similarity	NPD5141	Approved
0.5686	Remote Similarity	NPD6881	Approved
0.5686	Remote Similarity	NPD7320	Approved
0.5686	Remote Similarity	NPD6899	Approved
0.567	Remote Similarity	NPD7638	Approved
0.5652	Remote Similarity	NPD6051	Approved
0.5644	Remote Similarity	NPD6008	Approved
0.5644	Remote Similarity	NPD4767	Approved
0.5644	Remote Similarity	NPD4768	Approved
0.5631	Remote Similarity	NPD6372	Approved
0.5631	Remote Similarity	NPD6373	Approved
0.5612	Remote Similarity	NPD6404	Discontinued
0.5612	Remote Similarity	NPD7640	Approved
0.5612	Remote Similarity	NPD7639	Approved

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